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Knowledge Sharing in War Times

In both times of peace and times of turmoil, the context in which we operate evolves. It’s not a matter of whether these contexts exist, but rather how well-prepared you and your team are to navigate them.

As astutely stated by Becky Flint in her Peacetime CPO vs Wartime CPO article, the synergy between product and business success is undeniable, with people at the forefront. Your team’s ability to thrive amidst ever-changing circumstances hinges on their context and how you enable them. Beyond the tangible skills needed to weather change, there lies an intangible, unspoken element: the knowledge each individual possesses about the product, the team, the company, and the broader environment.

The Essence of Knowledge

Defining knowledge is a task that could extend beyond the scope of a single blog post. However, within our context, we can at least acknowledge that it encompasses more than just product expertise. It includes the ability to interpret company strategies, the acquisition of traits and behaviours necessary to be part of the team, and more. The sheer breadth of this knowledge is staggering.

Why Does It Matter?

Knowledge, as well as our unique interpretation of it, forms the core of our individuality. It’s what, coupled with our personalities, sets apart the contributions we make within our teams and, by extension, our business landscape. It’s akin to our mental model of the real world.

Considering that most endeavours involve a team, and each team member harbours their own mental models and experiences, the collective strength of a team rests on the expertise and contributions of its individual members.

The Challenge During Turbulence

In times of upheaval, pausing or dedicating time to share expertise with others can be an arduous undertaking. A study that Dragonboat conducted revealed that over half of Product Ops professionals identify “aligning cross-functional teams” as a significant challenge during quarterly planning, a hurdle that impedes business progress.

Suggestion: Watch on demand our CPO Series webinar “Aligning Around the Right Success Metrics”.

Navigating the Terrain

Among the myriad qualities of a wartime Chief Product Officer (CPO), one stands out: information mastery. Yet, there’s one aspect even more critical: speed. In an era where we demand rapid syncs, swift response mechanisms, and instant actions, decelerating seems implausible. But it’s crucial to remember that crashing at 120MPH is far harder (and potentially more disastrous) than slowing down.

If knowledge empowers us and defines our uniqueness, then having the right information at the right time equips us to be agile and efficient. When it comes to knowledge, here’s your immediate action plan:

1. Streamline Your Approach

Invest in well-documented, targeted rituals that can be anticipated. An agenda and the right audience are excellent starting points. Already documenting? Even better. When your documentation replaces a meeting, you’re a true efficiency champion.

2. Centralize Information

Strive to create a centralised repository where team members can easily access new knowledge. This includes ongoing tasks, holiday schedules, best practices, and past lessons learned. Imagine this repository as an extension of your brain — an autonomous resource that empowers your team while liberating you.

3. Construct for the Future

Invest time in crafting a robust information architecture that becomes your digital brain’s foundation. While the content within it evolves, the structure should remain steadfast. Think of it like the pods in a beehive: unchanging in size, yet accommodating the dynamic production of knowledge. Examples of these pods could be “Our Workflow,” “Strategic Direction,” “Collaboration Guidelines,” and more.

4. Promote the Culture

In the midst of challenges, evangelism becomes a vital skill. Convincing others that sharing knowledge is pivotal won’t happen overnight. But it won’t happen at all without investment. Understand that it takes time, and lead by example. Kickstart the movement by documenting your knowledge and showcasing its value to others. Remember, this is a divide-and-conquer strategy — win people over, one by one.

A Platform for Progress

Certainly, you’ll need a platform to facilitate this seamless exchange of knowledge. While jotting down every morsel of insight on paper sheets might sound tempting, there are better options. Enter Dragonboat — a tool designed to structure your team’s portfolio and foster real-time collaboration.

With Dragonboat, you can:

  • Enhance roadmap visibility
  • Optimize resource management
  • Monitor portfolio delivery
  • Align business goals with roadmaps

To discover how Dragonboat empowers product leaders and product operations teams across the globe to thrive amidst challenges, schedule a call with our experts.

Peacetime CPO VS. Wartime CPO

Ben Horowitz penned an article of Peacetime CEO vs Wartime CEO, in which he called out different approaches needed in leading companies during different times. 

As we know, when product wins, business has a chance to win; and when product fails, business will fail soon after. It’s not too far of a stretch to apply the same framework of leadership practice for Chief Product Officers (“CPOs”). That is, there are styles and techniques for a Peacetime CPO and for a Wartime CPO. 

What Does Peacetime Look Like?

According to Ben, “Peacetime in business means those times when a company has a large advantage vs. the competition in its core market, and its market is growing. In times of peace, the company can focus on expanding the market and reinforcing the company’s strengths.” For example, Google has enjoyed a very long peacetime where Google search dominates the market with very high return. 

What Does Wartime Look Like?

“In wartime, a company is fending off an imminent existential threat. Such a threat can come from a wide range of sources including competition, dramatic macro economic change, market change, supply chain change, and so forth.” An example is when Steve Jobs returned to Apple when it had only a few weeks of cash runway. 

What Time Are We In Now – Peacetime or Wartime?

By default, all startup CPOs are wartime CPOs – you are competing with big established players. You have a limited run way. If you are a CPO or head of product in a startup, you are a wartime CPO.

In today’s fast evolving technology landscape and post 0% interest rate era- peacetime has turned into wartime. 

There is hardly a company not in wartime now. Even for Google or Facebook, both had for decades enjoyed a major lead against competitors in an expanding market. And now both fighting their existential threat from AI and newcomers. 

How Do You Transition Into The Wartime CPO Practice?

Assume you are already in wartime mode or you are moving into wartime mode, how would the CPOs operate differently?  

First, let’s see the two styles in more detail. 

How Does A Peacetime CPO Lead?

  • Set BHAG – big hairy audacious goals 
  • Encourage more exploring, debating. 
  • Explore market opportunities. 
  • Give broad autonomy to teams. 
  • Not rushing. Efficiency is not important. Team can use any tool or process, from spreadsheet, slides to any bottoms up individually selected tools as decision speed is not a high priority. 

How Does A Wartime CPO Lead?

Wartime CPOs ask lots of questions and evaluate much closer on the changing landscape. Here are some of the key characteristics. 

What Changes Should You Make?

Transitioning from peacetime CPO to wartime CPO requires much more than just leadership style change. The entire organization must adjust too. How do you make it happen quickly without “burning down the house”? 

Here are some tips and learnings from CPOs who have done this before. 

Communicate The Change

Not everyone recognizes the change or needs for it. Leaders must communicate to align the team on the “why”.  So they are not blindsided by the changes, or resist them.  

Have The Right Process And Cadence In Place

  • Change your PDLC or roll out one if you don’t have it defined “on paper”. PDLC outlines how everyone in the product org, and those in GTM collaborate. (Check out  PDLC playbooks for outcome focused CPOs)
  • Have a more repeatable cadence of planning and communication. Speed and focus requires repeatable operating cadences. Everyone needs to know what’s expected and where to find information. 

Have The Right Platform 

When speed and focus are required in the collaboration across many teams and functions, an integrated platform is essential, not a nice to have. 

Moving fast should not be the reason for “(having) some babies thrown out with the bathwater” like what has happened at Twitter. 

Using a platform like Dragonboat, you will have immediate visibility on how to make shifts in allocation quickly with data to preserve the most critical talent when adjustment is unavoidable. 

With Dragonboat run your product operating system to orchestrate the cross functional teams to:

  1. Make effective, focused product investment decisions to drive revenue or lead competitors
  2. Watch outcome closely to adjust roadmap and priorities swiftly
  3. Manage your resources effectively to reduce bottlenecks and blocking dependencies.
  4. Still invest in the future, quarters or years out, just not decades out. 

To learn how Dragonboat helps CPOs and product leaders from both startups and Fortune 100 to complete and succeed effectively, schedule a call with our experts

Transforming From Project to Product

Executive Summary

With the rise of knowledge workers and distributed teams, companies are shifting away from a short-term, top-down project-based work culture, to a multi-horizon, agile, collaborative product ownership approach. 

Moving from a project to a product-centered mentality requires a culture change that does not happen quickly. If you want complete project-to-product transformation, unique areas throughout your organization will require holistic change. 

We found out, through the extensive experiences of our team, customers, and community members, that many people face these challenges:

  • Project-based planning and delivery
  • No visibility into other parts of the organization
  • A reactive approach to planning, strategizing, and team allocation
  • Focused on near-term results 
  • No single source of truth to continuously share progress

This article covers the learnings, observations, and experiences that prove helpful for organizations maneuvering the project-to-product transformation process.

CPOs Can Lead the Charge

A big part of any transformation will be around becoming outcome-focused. To do so, someone must champion a new paradigm—a portfolio management approach that aligns, synchronizes, and optimizes outcomes across your entire company. 

So, who leads this charge?

A Chief Product Officer (CPO) is a great place to start. The CPO champions a portfolio management approach that progresses the organization’s outcomes.

A CPO driving the project-to-product transformation focuses on:

  • Motivating teams and keeping them aligned on the overarching vision and mission
  • Helping navigate internal stakeholders to keep the product org viewed as a strategic partner as each functional area begins their change management process
  • Making the best investment decisions that drive outcomes

Becoming outcome-focused doesn’t happen overnight. It’s a journey. But there is a framework that many of today’s successful organizations use to guide the way.

The Hierarchy of Needs

As the change touches nearly every part of the organization, an integrated system must be implemented to support the change. To do so, you may need to understand the needs and interactions across roles and activities. 

The hierarchy of needs helps teams understand how they operate today while giving them a path forward to achieve the desired transformation. The following areas make up the hierarchy:

  • Building roadmaps
  • Managing portfolios
  • Delivering outcomes 

Each level contains a mix of the other components as an evolution that builds upon the foundation you laid in the previous area.

We recently wrote in-depth about this topic and covered everything from product ROI to outcome-focused roadmapping. Check out the entire framework and visual pyramid here.

Connect OKRs and Initiatives

For a project-to-product transformation to work, you need a single source of truth for product decisions. This requires the ability to connect OKRs and strategic initiatives.

  • Top-down: Align OKRs and strategies across all levels of your organization
  • Bottom-up: Empower innovation to achieve company-wide goals
  • Across team: Collaboration and dependency support

Communicating top-down alignment and showing visible support combined with bottom-up execution is a much more positive experience than a siloed approach led by individual teams.

Along with top-down support, all areas involved in building and supporting your product must be on board with the transition. It might be more challenging for some functions than others. For example, the finance team might struggle with product-based thinking because it isn’t necessarily how budgets have been traditionally managed or how they are accustomed to viewing the ROI. 

The CPO and other leadership must demonstrate empathy to these and other departments that may be resistant to change to garner their support.

Proper Portfolio Allocation

Transitioning from managing projects to managing a product portfolio requires proper resource planning and allocation. Organizations need to change from feature-based roadmaps to outcome-driven roadmaps.

Leveling up to a portfolio allocation mindset enables you to:

  • Achieve both long-term vision and near-term results
  • View the entire product portfolio through different lenses
  • Set target allocations by various swimlanes or bets
  • Review planned allocation and make real-time adjustments

Many Dragonboat customers use the Responsive Product Portfolio Management (Responsive PPM) framework to accomplish the above. Responsive PPM connects objectives, customer needs, products, and resources with execution. It accelerates outcomes responsive to the state of the organization and the market.

Unlike traditional project-based execution, which focuses on a group of projects and centralized governance, Responsive PPM focuses on continuously evolving products. This allows portfolio leaders to adapt and adjust in real-time to increase outcomes and product ROI.

Align on Metrics

During your transition from project to product, you will inevitably discover that every department has different KPIs that matter to them. This can create misalignment and strategies that work against each other.

To measure the success of your product, you need more than just monetary value. You need to replace ROI with Metrics over Available Resources or MoAR. 

MoAR is the ratio of relevant contribution of a product feature towards a metric used to measure a business outcome over the number of resources needed to achieve this contribution.

The MoAR formula enables a direct and holistic measure for portfolio planning and a clearer vision of product portfolio metrics. For a full breakdown of how it works, read the blog post “Forget ROI, Use MoAR for Product Portfolio Metrics.”

Remember that metrics viewed in isolation across various functions without understanding dependencies cause trouble. Metrics on…

  • Engineering velocity
  • Customer NPS
  • User engagement
  • Product delivery

…are all great but ineffective if not mapped back to business results.

Leverage Product Operations to Drive Transformation

Although we’ve only mentioned a few areas you’ll have to address in your project-to-product transformation, you will need someone to keep all the moving pieces connected. This is where product operations, or product ops, come into play.

The role of product ops is to enable an effective outcome-focused product organization, or a product-led company, to achieve the best portfolio outcomes. 

Phenomenal product op professionals help:

  • Clarify strategy across all levels 
  • Drive responsive execution that delivers commitments 
  • Help to scale without the business-damaging chaos
  • Lead the adoption of data-informed decision making
  • Balance long-term vision and short-term outcomes to win in the current and future market

How does a product ops team accomplish the above? You can group their work into eight areas:

  • Evolve product and p[ortfolio processes and tooling
  • Lead strategic and portfolio planning
  • Strengthen portfolio visibility and stakeholder engagement
  • Help define customer and user engagement initiatives
  • Standardize product analytics, experimentation, and launch planning
  • Advise on financial planning
  • Coordinates product tools and processes
  • Drives operational excellence through partnerships with leadership and HR


Understanding and executing across the areas mentioned in this post enable you to help drive your organization’s transformation. With thoughtful planning and helpful resources, you will achieve the project-to-product transformation you’ve been looking for. 

Our team is also here to support your efforts—book time today for a customized demo to see first-hand what Dragonboat can do.

product ops roadmap to success webinar

Big Hairy Audacious Goals (BHAGs) Using Outcome-Focused Portfolio Roadmapping

Executive Summary

A BHAG (pronounced “bee hag”) stands for Big Hairy Audacious Goal. It’s a simple yet powerful phrase that teams immediately connect with. Consider the following examples:

  • Starbucks: Become the most recognized & respected consumer brand in the world
  • NASA: Land humans on the moon
  • Amazon: Every book, ever printed, in any language, all available in less than 60 seconds (Amazon)
  • Microsoft: A computer on every desk in every home (Microsoft)
  • Stanford University: Become the Harvard of the west (Stanford University)

Despite the above examples having unique long-term visions, one aspect is consistent: the journey to success was not a straight line. 

So, what does this mean for today’s modern product teams?

If a strategy reflects the hypothesis on the best way to achieve a BHAG based on the current state of your product, team, available resources, and market conditions, how do you lead your team to achieve something grand? 

In this post, I explain why product leaders must evaluate, align, and adjust their strategies along the journey to achieve their BHAG. I also recommend ways to navigate the constant changes, uncertainty, and constraints you likely face. Let’s get started!

The Need for Portfolio Roadmaps

The former head of product at Asana, Jackie Bavaro, posed a great question on Twitter: How do I create a Product Strategy when all the CEO gives me is a revenue target? You can read the entire thread here, but here’s my favorite part:

A good product strategy has 3 parts: Vision (inspiring picture of the future), Framework (target market and what it takes to win, including pillars, principals, etc.), Roadmap (not a commitment, a wake-up call to see what it takes to achieve the vision in N years)

I’ll summarize the rest, but Jackie explains how a product leader needs to drive the conversations to connect the dots between the business goals and the product work while considering the top customer problems to solve. For each issue, brainstorm ways that solving the problem might achieve the business goal. Which one gets you closer to your BHAG?

Identifying the problem to solve is only the first step. Next, you have to decide how to implement it. How do you have a feature-based roadmap where everyone knows what’s coming and an outcome-based roadmap to illustrate the framework and outcomes? 

Feature Roadmap vs. Outcome Roadmaps

Here are a few great examples of hypothetical roadmaps by Gibson Biddle, former head of product at Netflix/Chegg.

Feature Roadmap

Outcome Roadmap

Hopefully, these example roadmaps give you a sense of the critical differences between a feature roadmap and an outcome roadmap. But keep in mind that these are only two examples. A roadmap has even more flavors based on the lens you look through and who your audience is.

Because of the need for multiple roadmaps, companies created multiple slide decks to represent vision, strategy, and BHAG in various ways to illustrate and communicate their plans. 

With Dragonboat, you can create and communicate real-time portfolio roadmaps and switch your lens with a few clicks to get a different new perspective—all using the same data. It’s one integrated platform that helps build product roadmaps that accelerate portfolio outcomes. 

Our customers call this unique ability “slice and dice” portfolio roadmapping. 

Building Outcome-Focused Roadmaps in Dragonboat

If you want to try this framework with your own data, start a free trial and play around! Here is what to do first:

  • Consider how your executives talk about strategies, goals, and BHAGs.
  • What terms do you use? (swimlanes, value stream, horizon, goals, themes, OKRs)

These are the anchors you will use to organize your portfolio in Dragonboat. They are open-ended by design. Often you may have company or portfolio-wide goals with team-level goals nested underneath. You can use this hierarchy to set up your product portfolio—giving you a dynamic ability to switch “lenses” and quickly view your plans from different perspectives.

Note: If you have multiple independent products with individual goals or themes, send a message to your Dragonboat CSM and ask them to turn on the “portfolio marker” feature, where you may mark whether a goal or theme applies to the entire portfolio or one product area. 

Next, let’s talk about the timeframes.

  • Do you use a quarterly horizon for the next 4 quarters? 
  • Or do you take a “lean roadmap” approach with Now/Next/ Later? 

Having both is also okay!

Here is a template of Rolling Quarterly Roadmap based on the Netflix example above.

Here is a template for fuzzy timeframes like Now Next or Later based on the Outcome Roadmap Template of the Netflix example.

With timeframes established, you’ll want to focus on your next level of leaders: Directors and Managers.

How can they translate the goals, strategies, or outcomes to their day-to-day work? The work is often referred to as features, initiatives, or bets, and they:

  • Map to specific goals and strategies
  • Defined with a high-level scope and duration
  • Contain an owner who is responsible for driving the work forward

A feature represents an Epic that’s typically done by a team in a few sprints. And an initiative typically represents a basket of features that have a tangible impact on specific outcomes. Initiatives involve multiple teams and last for a quarter or more.

In larger organizations, you may have strategic bets that last half a year or longer with significant resources devoted across many teams. 

Another element for consideration is how your product team is structured. Some teams call these different lenses Roadmap and Sub-Roadmap. Others call it Product Group and Product. At the same time, others may have Pods and Squads. 

No matter what you call it, you can define your portfolio through the lens that makes the most sense to your product team while giving everyone a space to focus and coordinate their plans. 


As no product is built by a single team, having a source of truth with a consistent and holistic view enables effective communication, planning, executing, and ultimately, achieving your BHAG! 

Dragonboat supports high-level strategic planning but gives you the flexibility in timeframe and team-specific planning to make things work for all teams. And it does it all in one product roadmapping and portfolio management platform. 

Why Dragonboat CTA

How to Hire and Evaluate Your Next Chief Product Officer

Executive Summary

Every company needs a Chief Product Officer (CPO). Why? Because someone needs to champion a portfolio management approach that optimizes outcomes across the entire enterprise.

Managing a portfolio isn’t about the number of product lines or your platform’s size but rather about collaboration and managing complexity while delivering outcomes. When an organization is ready to mature its product management discipline and hit significant revenue growth milestones, it’s time to put a product leader at the executive table.

Here are a few questions to ask if you’re unsure that your company needs to hire a Chief Product Officer:

  • Are you yearning for a portfolio approach to balance the needs of customers, business goals (OKRs), and engineering capabilities to achieve the best product outcomes?
  • Do you want more flexibility, agility, and responsiveness when planning, strategizing and allocating resources?
  • Do you need someone who can achieve near-term results while maintaining a long-term vision with limited time and resources?
  • Are you looking for someone to continuously promote progress and share a single source of truth, driving transparency and trust across all teams?

Answering yes to the above is your sign—it’s time to bring in someone who can effectively collaborate with key functions involved in building and delivering products. 

In this post, I’ll share the top secrets to finding a phenomenal Chief Product Officer and how to evaluate their impact. A special thanks to Melissa Perri, CEO of Produx Labs and the author of “Escaping the Build Trap,” who shared some of these secrets during her CPO Series Q&A

7 Traits to Look for in a Great CPO

Most great Chief Product Officers have more than just deep product-related experience. They possess the ability to build relationships with other functional leaders early and understand how the rest of the company operates.

These are the traits you should look for when searching for a CPO:

Takes initiative: Chief Product Officers need to take the initiative. They don’t just sit there and wait for permission to align cross-functional teams and get them to deliver outcomes. They constantly maximize their efforts toward achieving the company’s strategic goals. 

Forges relationships: From executive buy-in to team lead alignment, a great CPO is a master of maneuvering relationships and bringing teams together for a single, shared vision. They keep everyone on track for short-term goals while helping them understand the long-term vision.

Financially savvy: A Chief Product Officer should have deep experience with the business’s financials. They need to understand how the actual financials of the company work and be able to connect their strategies to their impact on the business model. The more a CPO is willing to dive into the finances and forge a relationship with the CFO, the more likely they will succeed.

Board-ready: Managing up and presenting to the board is no easy task. You need a CPO who can present their ideas clearly and discuss challenging problems in a very diplomatic, convincing, and straightforward way. The best Chief Product Officers are humble enough to admit mistakes and build true partnerships with board members by asking questions and listening.

Says no but explains why: It’s easy to say no. Most people stop there. A CPO says no in a way that helps everyone understand the “why.” This nuanced communication preserves relationships and allows everyone to move forward in the same direction.

Strategically-minded: Great Chief Product Officers leverage strategic frameworks that guide product decisions across all levels of the organization. They define the strategic drivers, standardize prioritization efforts, and allocate resources towards objectives (OKRs) and initiatives.

Makes data-driven decisions: Chief Product Officers make decisions based on data by measuring outcomes to influence the next iteration of product strategy. They assess resourcing needs, progress tracking, and scenarios using real-time data. A responsive approach to planning, strategizing, and allocating allows Chief Product Officers to adjust their plans dynamically.

Check out this clip from our CPO Series of Melissa Perri where she reveals what she looks for when hiring a Chief Product Officer:

Should You Promote Someone to VP or Hire a CPO?

Depending on the company’s size, you could have a VP of Product while also needing to bring on a CPO. 

A VP of Product typically:

  • Manages and scales one or two products
  • Focuses on coaching and mentoring product managers

A CPO typically:

  • Collaborates and aligns the C-suite on the right business strategy to execute
  • Connects financial outcomes and product roadmaps back to what the C-suite’s doing 
  • Interfaces with the board and with the rest of the executives
  • Focuses on building teams underneath them that can scale

“What it really comes down to is understanding the ROI and making sure that you get ROI from your product investments. That’s what a Chief Product Officer is going to bring to the table. They’re going to make sure that you are building the right things that will get a return for your company. And they’re making sure that you can scale appropriately with that.”

Melissa Perri

Evaluate Your CPO Against These 5 Areas

The most successful Chief Product Officers make an impact within their first 90 days. However, they don’t worry about massive, overarching changes right away. Instead, they focus on:

  • Using curiosity to assess the current situation
  • Building deep relationships while aligning goals
  • Introducing new internal structures but not sweeping changes
  • Providing a source of truth that brings org-wide visibility

If you’re a new CPO and haven’t formalized your success plan, read this: The 90-Day Success Plan for New Chief Product Officers.

If your CPO has been in place, here are the key criteria you should use to evaluate their impact:

Product Strategy

Your Chief Product Officer should be the driving force in developing the product strategy, including honing key persona targets, as well as the product’s value proposition, segmentation, price, and monetization strategies. They should also create, maintain, and share portfolio-level views of the product roadmap while championing the long-term vision. A CPO understands that the best product strategy is developed across the entire leadership team and is only successful if there is alignment from all teams from development through execution.

Product Management

If the company views the product team as a strategic partner versus just an order taker, your CPO is doing something right. This means your Chief Product Officer has developed the core product management discipline leveraging people, processes, and product portfolio management tools to distribute responsibilities across the entire team to accelerate outcomes.

Metrics and Process

Successful CPOs track and monitor metrics and take a data-driven approach to product operations. They use data to align priorities across revenue, customers, operations, and business stakeholders. They also know how to manage financial outcomes and share these with the broader organization. A CPO should have a successful track record of systematically developing and implementing across the core product management process and can demonstrate they know how to lead an organization through transformative changes.

Org Builder and Coach

A Chief Product Officer should have a proven track record of hiring and developing your product organization. They know how to drive top-down alignment while empowering loosely coupled teams with bottom-up innovation—keeping everyone aligned on short-term goals and the larger-scale vision. Across the product org, you should see a balance of employees your Chief Product Officer has brought on: former colleagues, new employees, and teammates promoted from within. At the end of the day, the CPO creates a culture of trust, motivating the entire team to execute and deliver results. 

Internal Collaboration

The primary job of a Chief Product Officer is to drive business outcomes while effectively collaborating with critical functions involved in building and delivering products. They should be orchestrating deep collaboration between product, design, customer success, marketing, and engineering. CPOs create a cohesive framework that connects vision and goals with initiatives and features while guiding each team’s best practices and decision-making. They plan roadmaps and assess allocation in real-time across all product levels, perform trade-off analyses with functional leaders, and prioritize within the context of business goals, customer needs, and product strategies using MoAR (or their own customize prioritization framework).


If your organization is ready to accelerate portfolio outcomes, consider bringing in a Chief Product Officer to lead the charge. In today’s landscape, you need someone who can:

  • Connect objectives with initiatives
  • Build data-driven roadmaps
  • Collaborate with cross-functional leaders
  • Adjust allocation based on outcomes

A successful Chief Product Officer will bring strategic clarity across all levels of the organization. They’ll also drive responsive execution that delivers against your company’s goals. If you’ve been striving for a balance of long-term vision and short-term outcomes, a great Chief Product Officer will do exactly that. 

So, don’t wait. Now is the time to elevate your product organization and balance the right outcomes at the right time—with a Chief Product Officerbringing everything together.

PS: Don’t miss it – Chief Product Officers from market-leading companies like Shopify, Pendo, and Procore are sharing their unique insights during our CPO Series. Check out the line-up and register to join the next session

Fintech Product Portfolio Management: How Outcome-Focused Teams Scale

Fintech (financial technology) is a cutthroat, complex, and increasingly competitive industry. With the need for increased speed to market to stay competitive, fintech product leaders need to run their product portfolio like a well-oiled machine. Operating in a highly regulated industry requires flexibility, adaptability, and frequent pivots due to external and regulatory changes. Layering on top of that is dependencies.

In this post, I’ll cover how to run an effective fintech product team at scale:

  • Key factors that set fintech companies (fintechs) apart
  • The key strategies for fintech success
  • How to execute winning fintech strategies

What Sets Fintechs Apart?

To ensure success in this space, we must first address what sets fintechs apart from other industries.

Where fintechs may be easy to start, they are hard to scale. There are a couple of reasons that make fintechs challenging to scale. Let’s take a look at some of the most common reasons:

  • Fintechs sell complex products with different users, segments, and use cases.
  • Global operations are typically “forced.”
  • They constantly face shifting legal and regulatory requirements.
  • Most require a strong dependency on third parties or external vendors for core capabilities.
  • There is fierce competition from existing traditional financial institutions and incumbents.
  • Unless you are doing lending, fintech is a very thin margin business.

Because the fintech industry is complex by nature, companies either need massive capital investments or execute practices to thrive in the environment to survive. In the absence of the former, a few key strategies will pave the way for fintech success. 

Key Strategies for Fintech Product Portfolio Management Success

Now that we understand the unique traits of the fintech industry, we can get into setting your team and company up for success. Let’s break down the process:

  1. Reach ubiquity as fast as you can 
  2. Drive use-case expansion
  3. Boost margins
  4. Partner with mergers and acquisitions (M&A)

1. Reach Ubiquity As Fast As You Can

To achieve ubiquity, fintech companies must ship smart and fast with a single product early on. 

One of the best examples of this comes from the $60 billion company, Block Inc. (formerly Square Inc.). 

In its conception, Block started small before it had several digital service products. The team began with a card reader dongle that consumers could use with their phones, allowing them to accept payments anywhere. This initial focus on one product allowed Block to stay top-of-mind for its target customer, small merchants, and it opened the door for expanded adoption.

2. Drive Use-Case Expansion

Use-case expansion is about allocating new products as soon as there is the first sign of product-market fit. 

“Ubiquity and use case expansion really have to come together immediately one after another. Fintech is a cutthroat industry, so your next focus is how can our company improve adoption? That’s why use-case expansion is the immediate focus after ubiquity.”

Becky Flint, CEO and Founder of Dragonboat

In PayPal’s early days as a part of eBay, its strategy was simply to “thrive on eBay.” The PayPal team wanted to capture as much market share and volume as possible. However, there was a flaw in remaining in the ubiquity phase, resulting in missed growth. 

PayPal noticed that there was a gap in eBay’s market and that a lot of merchants were not selling on eBay. That’s when PayPal transitioned into driving use-case expansion and set out to target those people. That is when the real growth began. 

In 2006, eBay was more than 75% of PayPal’s revenue, and by 2015, it made up only 15%. Ultimately eBay and PayPal split, and PayPal went on to be a $90 billion company. 

If you continuously focus on improving your existing product, you will overlook significant new business opportunities, ultimately diminishing returns and hamper continued growth.

3. Boost Margins

To stay competitive in fintech, companies need to boost their margins. However, fintech is a thin-margin business, so how can you increase margins as a way to scale?

“With no infinite amount of funding, boosting margins is no easy task. This is what makes fintech product managers so unique because in order to be successful, they must be business savvy.”

Becky Flint, CEO and Founder of Dragonboat

Fintechs operate in a fast-moving market, so to boost margins at a scaling fintech, you have to look at the market and the changing landscape. Let’s check out what PayPal did back in the day.

At the time, when you used a credit card globally, there would be a foreign exchange fee somewhere around 3%, which was cutting the margin.

PayPal saw this as an opportunity. As a global company, it already had multiple currencies, so PayPal sought to do an internal exchange. That way, instead of letting a credit card company handle foreign exchange fees at 3%, consumers could have PayPal take it for only 2%—a win-win for everyone.

4. Partner with Mergers and Acquisitions (M&A)

Lastly, most successful scaling fintech companies eventually partner with mergers and acquisitions to fully mature their business.

2021 was the most active year for fintech M&A, and 2022 is tracking to yield similar results.

There are a few reasons fintech companies partner with M&A. Most importantly, it allows them to diversify the products they offer, get ahead of the competition, and succeed in a global market.

For example, Block acquired the Australian Buy Now, Pay Later (BNPL) firm Afterpay in Australia’s biggest ever buyout to capitalize on the boom in the Buy Now, Pay Later space and remain competitive. Jack Dorsey, co-founder and CEO of Block, remarked, “Together, we can better connect our Cash App and Seller ecosystems to deliver even more compelling products and services for merchants and consumers, putting the power back in their hands.”

Another example of an M&A to stay competitive and innovative is Paypal’s move to acquire cloud-based infrastructure Curv for digital asset security, expanding its initiatives to support cryptocurrencies and digital assets. 

How Can You Execute Winning Fintech Strategies?

So now that we have covered “the what,” let’s get into “the how.” A winning fintech strategy requires a responsive portfolio workflow. 

As fintech goes through various phases of evolution, from ubiquity to use-case, product leaders need to be able to adjust quickly. A portfolio workflow gives you the ability to see your roadmap. This is key for product companies that are complex and scaling to catch potential problems early.

A responsive portfolio workflow is unique for its three-directional movement: 

  • Top-down alignment – Provides the overall direction of where the company wants to go to help focus on the additional ways to grow.
  • Bottom-up empowerment – Brings the product to more markets. With the overall direction paved, bottom-up empowerment provides new ideas and concepts to take the company to the next level.
  • Cross-team collaboration – An effective, responsive portfolio workflow requires multiple teams to come together to execute bottom-up empowerment and reach the vision and direction established by top-down alignment.

Implementing a Responsive Fintech Product Portfolio Workflow

With a responsive portfolio workflow (and the right outcome-focused platform), fintech teams can achieve business goals, manage multiple teams, and scale. Let’s look at an overview of how you can implement an outcome-driven product management workflow

Step 1: Define Objectives

The first step is to make sure you can see what to focus on and how various teams will support your many goals. Fintech is complex, and so you need to be able to see the dependencies across all levels of your organization.

After defining goals and strategies, you need to consider how to support them.

Step 2: Set Allocation/Estimates Along Multiple Dimensions

Strategy without resource allocation is a pipedream.

Think about your allocation in three dimensions:

  1. Segment
  2. Region
  3. Product

The ability for your fintech to scale is directly correlated to your ability to see your portfolio in different dimensions and allocate resources against the strategy. That is the key differentiator between successful and unsuccessful.

Step 3: Connect Goals, Strategies, and Execution

In fintech, there are multiple levels of dependencies, and they require various teams to support initiatives. Connecting goals, strategy, and execution is vital to avoid misalignment and chaos.

This is one area a tool can visualize how everything ties together, from your feature goals to your team contributions. ​​This alignment will push your organization forward by making product roadmap planning, resourcing, progress tracking, and communication much more effortless.

Step 4: Prioritize Across Teams

When you start thinking about product strategy going from ubiquity to use case, your efforts need to connect allocation across all dimensions and tie that to your product and prioritization process. This shift in mentality helps companies evolve to where they want to be.

When looking to visualize how your allocation ties to goals, it doesn’t have to be 100% accurate. The idea is that you can quickly understand if you are performing well (i.e., over or under-allocating).

Pictured: Dragonboat demonstrating how strategies line up and how your work contributes to your goals and how you allocate to the previous target.

Step 5: Ensure Delivery

Once everything is set in its dimensions, you must be sure you are moving the needle.

Product and delivery in fintech are complex. The ability to see the roadmap and metrics tied to it will help a company see the problems and the changes.

Portfolio tools will allow you to see real-time updates and check in with the progress of your product. From there, you can use responsive reallocation to make any needed adjustments.

Step 6: Responsive Re/allocation

Responsive allocation is looking at your product and the road bumps it is facing and making adjustments to it to point your product in the right direction.

That is why having the ability to see your roadmap and the items tied to it is so vital for a complex, scaling company. Especially in fintech, many phases of evolution make a responsive workflow and outcome-focus planning key to success.

Manage Your Fintech Product Suite Like a Financial Portfolio

A portfolio-based approach will allow you to focus on core business and strategy to find winning products. You can use proven success and earlier success to adjust and reallocate.

In summary, winning portfolio workflows require fintech companies to be responsive, top-down, bottom-up, and across teams and adaptable depending on where you are in your business. The portfolio process starts by aligning on goals and strategy. This framework allows your company to manifest great products from different initiatives led by various teams.

nium dragonboat product portfolio management case study

What is a Chief Product Officer (CPO) and What Do They Do?

An exceptional, outcome-focused product portfolio is vital to every company’s success. So as organizations grow, so does their need for a Chief Product Officer (CPO) who can rise above the day-to-day and take a more holistic view while leading the product team. In the following post, we perform a deep dive into this critical position, so you can decide how it fits within your organization or career path.

What is a Chief Product Officer (CPO)?

A Chief Product Officer (CPO) is an executive-level position that oversees a company’s product organization and portfolio(s) to ensure they deliver value to the customer while meeting its strategic goals and objectives. Sometimes referred to as the “Head of Product,” this is a cross-functional role responsible for designing, building, and delivering solutions and bottom-line impact. 

To this end, CPOs focus on the following:

  • Making strategic product investment decisions that drive outcomes.
  • Building and motivating a world-class product team to deliver on the company’s vision and mission.
  • Collaborating with internal stakeholders throughout the product life cycle and positioning the product organization as a strategic partner vs. an order taker.

It may help to remember that Chief Product Officers don’t build the product themselves. Nor do they design, code, or write marketing materials. Instead, a CPO connects all product-related activities to the company’s overarching strategy by collaborating with:

  • Engineering for product development work.
  • Marketing for positioning and messaging.
  • Sales for pricing, demos, and closing.
  • Customer success for continued adoption, upsell, and cross-sell opportunities.
  • Finance for budgeting and identifying ways to optimize gross and net margins.

In other words, the primary job of a Chief Product Officer is to drive business outcomes by effectively collaborating with key functions involved in building and delivering meaningful products. They set a top-down strategy that balances multiple dimensions while encouraging bottom-up innovation.

What Does a CPO Do?

Company leaders holding a meeting to illustrate what a Chief Product Officer does.

Chief Product Officers collaborate with the various functions required to develop products. And great CPOs apply a portfolio approach that helps them balance customers’ needs, business goals (OKRs), and engineering capabilities to achieve the best outcomes. To accomplish this challenging task, CPOs:

  • Take a responsive approach to planning, strategizing, and allocating, and dynamically re-adjust in real-time.
  • Work to achieve near-term results and long-term vision with limited time and resources.
  • Continuously promote progress and build trust by developing one transparent source of truth to communicate and champion ideas, plans, and progression.

In organizations where the CPO role is new, this can be a challenge because they must switch their mentality from delivering features to driving outcomes. In addition, it requires a broader perspective, moving from one product to the entire portfolio and managing multiple functions. For example, Chief Product Officer responsibilities typically include the following.

Product Strategy: The Chief Product Officer outlines a comprehensive product strategy encompassing the whole portfolio. They are responsible for the “why” of the product, ensuring the product direction fulfills the company’s strategic vision and delivers meaningful outcomes.

Design and Development: The CPO may completely own product design and development in smaller organizations. Whereas at larger companies, these functions can fall under multiple leaders. For example, a Chief Technology Officer might also work with the product team, but their focus is on enablement (how to get things done). Regardless, the CPO influences both teams. 

Product Marketing and Sales: Chief Product Officers represent the voice of the customer internally, communicating insights from research and analysis about the customer experience with the marketing and sales teams. They also interface with these groups when creating the ideal customer journey, from product awareness to onboarding and buying additional products and services. This collaboration focuses on customer retention and is a crucial product, marketing, and sales metric. 

No matter where they get involved, the CPO aligns the product direction with the company vision. They anticipate needs and challenges and adjust responsively to changing internal and external conditions.

How Do CPOs Differ From Other Product Leaders?

Example product team organizational chart in a company with a Chief Product Officer on the executive team.

Chief Product Officers are at the top of the organizational structure, leading the entire product organization, portfolio, or sometimes a portfolio of portfolios. As such, all other product leader roles and functions typically ladder up the CPO:

  • VP of Product: Owns a product line or a group of products.
  • Director of Product: Owns a set of product areas or a single product. 
  • Product Manager: Owns an individual product area. And depending on the organization, the product management function may consist of many product and senior product managers.

Chief Product Officers serve as mentors and influence the product department’s dynamics but rely on other product leaders to manage the day-to-day while focusing their time on collaborating with functional leaders to influence strategic direction by:

  • Effectively communicating company goals.
  • Providing visibility into roadmap strategy and planning.
  • Delivering stakeholder reports to define objectives and show progress.
  • Communicating the why behind prioritization decisions.

Great product portfolios only come to life through great collaboration. That is why multiple cross-functional teams must come together to deliver significant outputs. To realize the vision, the CPO helps define a long-term plan that outlines how they will turn ideas into impactful product experiences that drive revenue. This strategy must consider resourcing needs and dependencies and connect the high-level objectives and key results (OKRs) to day-to-day execution.

To bring a winning product portfolio to market, a CPO must orchestrate the efforts of all departments—communicating the vision and ensuring everyone stays aligned with the common goals.

What Skills Do Companies Look for In a CPO?

When hiring a Chief Product Officer, companies look for more than product-related experience. The CPO is a highly visible and strategic role, so this person must be capable of seeing the big picture and building healthy working relationships with leaders across all business areas. So, in addition to technical knowledge, below are the critical traits and skills most successful CPOs possess:

Leadership Skills: Chief Product Officers must motivate cross-functional teams to maximize their efforts toward achieving the company’s strategic goals. Their success depends on their ability to unify various groups to keep everyone aligned, focused, and motivated to pursue a shared vision.

Influence and Communication Skills: CPOs interface with many stakeholders, which requires clear, concise, and (sometimes) persuasive communication. From board members and Executives to product teams and customers, the CPO needs to share the product vision and plans for fulfillment continuously. 

Strategic Thinking Skills: Great CPOs use strategic frameworks that guide product decisions across all levels of the organization. They define the strategic drivers, standardize prioritization efforts, and allocate resources to ensure the team can confidently pursue critical initiatives and objectives (OKRs).

Data-driven Decision Making: Chief Product Officers make decisions based on data. They identify Key Performance indicators (KPIs), measure outcomes, and use what they learn to influence the next iteration of product strategy. They also assess resourcing needs, track progress, and run what-if scenarios using real-time data. Most use a responsive approach to planning, strategizing, and allocating, which allows them to use data to adjust their plans dynamically.

Roadmap Transparency: Creating and sharing roadmaps is one thing, but most companies want a CPO who provides clear visibility into their progress, with roll-ups at all levels and by any dimension (ideally, in real-time). So, a strong CPO knows how to collect and report that information, typically with the help of a product portfolio tool

“What it really comes down to is understanding the ROI and making sure that you get ROI from your product investments. That’s what a Chief Product Officer is going to bring to the table. They’re going to make sure that you are building the right things that will get a return for your company. And they’re making sure that you can scale appropriately with that.” 

Melissa Perri on the difference between a VP of Product and a CPO

Does Every Company Need A CPO?

Simply put, yes! 

Every company needs someone championing the overall product vision and a portfolio approach because every organization’s product or product lines need to support multiple goals, segments, and themes. Product portfolio management isn’t about the size of the portfolio but rather about the craft of managing complexity and delivering the best product outcomes given constraints. Product leaders must do this work to ensure product performance. 

If your company isn’t sure it needs a Chief Product Officer, consider these questions:

  • Do you want to become outcome-focused and escape the build trap?
  • Do you want to keep mandating initiatives or start providing strategic intent?
  • Do you need a new framework that connects OKRs with Agile execution?
  • Do you need to align priorities across revenue, customers, operations, and business stakeholders?
  • Do you need to connect the dots between all moving pieces for real-time portfolio planning and allocation?

If you answered yes to any of these questions, you need a CPO.

The Bottom Line

The Chief Product Officer role is essential for organizations that want to deliver an exceptional product experience while being mindful of the business’s constraints. Chief Product Officers enable cross-team collaboration, drive top-down strategy, and empower bottom-up innovation so they can deliver meaningful products while achieving results. As such, a great CPO will lead an organization toward the following: 

To learn more about the CPO role, check out our 90-Day Success Plan for New Chief Product Officers named ‘Most Valuable Post of 2022’ by Product Management Today.

Wyatt Jenkins Dragonboat Testimonial

The 90-Day Success Plan for New Chief Product Officers

Executive Summary

When embarking on a new challenge with a new company, the most successful Chief Product Officers (CPOs) do an incredible job making an impact within their first 90 days. They don’t worry about massive, overarching changes. Instead, they focus on:

  1. Using curiosity to assess the current situation
  2. Building deep relationships while aligning goals
  3. Introducing new internal structures but not sweeping changes
  4. Providing a source of truth that brings org-wide visibility

Start slow. Accomplishing the above in your first 90 days ensures you’ll establish credibility. You don’t want to be the new Chief Product Officer that comes in too hot—quickly making overhauls and rapidly changing everything without the proper context. You’ll likely step on people’s toes and have difficulty building the trust you need for your long-term vision if you do. 

In this post, I dive deeper into the four areas of focus. I also outline tangible examples for quick wins. These are key takeaways that you can use to guide your 90-day success plan. 

New CPOs Wanted

Search for “Chief Product Officer jobs” and see how many listings appear. 14,797. That’s the number you’ll see on various job boards (at least at the time of this writing). There’s good reason so many companies are waking up to the need for this pivotal role. 

The Chief Product Officer oversees an organization’s entire product portfolio while:

  • Tying product work to company strategy
  • Making the best investment decisions that drive outcomes
  • Keeping their teams motivated and focused
  • Helping navigate internal stakeholders to keep the product org viewed as a strategic partner, not an order taker or feature farm.  

Chief Product Officers balance multiple dimensions, including customer needs, business goals, and engineering resources. They set the top-down strategy and empower their teams to create the bottom-up plan.

After talking with dozens of CPOs, I’ve found that there are two trends:

  • CPOs are the newest role in the C-Suite 
  • The most significant skill gap for new CPOs is portfolio management

These trends don’t surprise me. The CPO role is very fresh and new to many organizations. It requires a mentality change from delivering features to driving outcomes. It also means taking a broader perspective, from one product to the entire portfolio. 

But the Chief Product Officer cannot do it alone. They must communicate effectively and collaborate with the Chief Financial Officer (CFO) for budget, the Chief Revenue Officer (CRO) to drive revenue, and the Chief Customer Officer (CCO) to retain customers. 

The responsibilities of a Chief Product Officer come with pressure and an expectation to implement meaningful change with significant results. This is precisely why I’m writing this blog post—to give you a 90-day success plan so you can lead your product organization with confidence. 

Here are the most critical areas to focus on in your first 90 days as Chief Product Officer:

Assess the Situation With Curiosity

Before you do anything with the product, you first need to understand what’s working and what’s not. Prior to implementing changes, go on a listening tour. 

  • Spend time with direct reports and cross-functional peers
  • Find out everything you can about the immediate problems and uncover unknowns
  • Validate your assumptions and start to create a short-term roadmap

The goal is to look for quick wins and alignment with the new team. You want to discover areas of opportunity and identify things you can put into place fast to establish trust. Fix inefficiencies to create more bandwidth with the existing resources. This isn’t the time to think about who you’re going to hire or how to implement a brand new strategy—it’s all about understanding what’s been done to date, what works, what doesn’t, and how you can drive immediate impact with the existing team. 

You’ll now have a set of assumptions to validate with your stakeholders as you build your plan and create your roadmaps.

Build Deep Relationships and Align Goals

This may sound counterintuitive, but your peers are more important than your boss outside of direct reports. Why? Because delivering real product innovation requires a true partnership from your cross-functional cohort, the Chief Revenue Officer, Chief Technology Officer, and Chief Financial Officer (just to name a few). This group must maintain alignment to ensure product development initiatives don’t fall into the build-trap—building features without having visibility into their impact on company goals.  

When collaborating with your peers, you want to find a balance between everyone’s needs. There will inevitably be competition and contention for resources and prioritization considerations. Use metrics and numbers as your friend to effectively communicate why the roadmap decisions you make will significantly impact the broader organization. Visibility is key to alignment and buy-in.

  • Understand the challenges and desires of each functional area
  • Map these areas back to your roadmap and keep everyone aligned on the outcomes you’re trying to achieve
  • Prevent one group from overpowering the product direction
  • Help everyone understand the trade-offs of prioritization and how requests fit into the higher-level strategy

Another important stakeholder is your boss’s boss. As CPO, you should have visibility with the board, partners, and customers. Ensure you’re validating your plan and creating alignment with all key stakeholders at every level. 

Create a New Structure

Now it is time to create a new structure, but not an organizational structure, a new communication, operations, and delivery structure. You can’t completely overhaul corporate operations in 90 days, but you can evolve this layer within the product org. Start by making the shift from building features to becoming outcome-focused. 

In tackling this now, you’ll create a culture from the beginning around how your work connects to company goals. You’ll also set your department up for success by showing how it is a strategic driver of the organization’s ability to succeed and stay competitive.

To accomplish this, Chief Product Officers need someone who can become their right hand. 

  • Bring on a product operations role or up-level someone to fill this gap
  • Product Ops will help you run the strategic operations of your org to enable an influential, outcome-focused group
  • Think of Product Ops as the COO of the product org

Putting a good ops structure in place from the start ensures you facilitate a healthy rhythm of alignment across goals, strategies, and prioritization. It also forces compelling product delivery cadences and stakeholder engagements, which are crucial to your success.

Deliver Quick Wins and Provide a Source of Truth

Today’s most successful businesses and product leaders realize that spreadsheets and docs are no way to run a real business. Wins don’t always have to be shiny new features. Sometimes the most impactful wins are around:

  • Providing visibility into roadmap strategy and plan
  • Stakeholder reporting to understand objectives and progress
  • Communicating the why behind prioritization decisions

To provide this level of detail, you’ll need to create a strategic framework that guides product decisions across all levels. You’ll need a portfolio management tool to help. 

With a modern tool in place, you’ll be able to:

  • Define your strategic drivers
  • Standardize your prioritization framework
  • Set resource allocation towards objectives (OKRs) and initiatives

Now your team can make the best product decisions across the portfolio to deliver customer delight and business outcomes.

Lastly, share away! 

You’ll want to view and share roadmap progress roll-ups at all levels by dimension and in real-time. This requires specific roadmaps for each unique audience. A portfolio platform will allow you to quickly create and share these views in a few clicks, using the same real-time data. 

Can’t decide what type of tool you need? We have a guide for you: How to Choose Between a Roadmap and Product Portfolio Management Tool

Congratulations! With this level of visibility, you have created one central source of truth—all within your first 90 days. That in and of itself is an accomplishment worth celebrating. 


Here’s what I think the next wave of great Chief Product Officers will focus on to be successful:

  • Applying a portfolio approach to balance the needs of customers, business goals (OKRs), and engineering capabilities to achieve the best product outcome
  • Taking a responsive approach to planning, strategizing, allocating, and dynamically re-adjusting
  • Achieving near-term results and long-term vision within limited time and resources
  • Continuously promoting progress and sharing the source of truth, believing that transparency creates trust

Final thought: As a new Chief Product Officer, you have the opportunity to shape what greatness looks like for this role. There’s never been a better time to lean in, learn new product frameworks built for portfolio leaders, and adapt and adjust in real time.  

Wyatt Jenkins Dragonboat Testimonial

Our Favorite Moments From ProductCon 2022

Recently, we partnered with Product School to bring more insights and learning opportunities to ProductCon 2022, the world’s largest product management conference. Held virtually via the Hopin platform, over 20,000 product people attended from all over the globe. In addition to the event’s main stage sessions, we hosted five of our own sessions in the Dragonboat expo booth, including a keynote featuring Melissa Perri. We also held expert Q&A sessions and panel discussions on a wide variety of topics ranging from product ops to responsive product portfolio management

Didn’t get to attend? Here’s a recap of our favorite moments from ProductCon 2022!

1. The Good Vibes From DJ Will Gill

DJ Will Gill, who was named the #1 virtual event DJ by Wall Street Journal, proved that just because an event is virtual doesn’t mean you have to miss out on the fun! From the beginning of the day and all throughout, conference-goers could take a break from the action and enter the DJ booth where he played fun, upbeat songs that made you want to get up and dance. This positive energy and good vibes definitely helped to set the tone for the event and make it a more fun experience for everyone tuning in from home or the office. 

2. Chris Butler and Becky Flint’s Chat About Kicking Off Product Ops in 2022

Our first Dragonboat Expo session centered around one of our favorite roles in product: product ops. Continuing the discussion from a recent chat on kicking off product ops, Chris Butler, Global Head of Product Operations at Cognizant, joined our CEO, Becky Flint, to take live questions from the audience about product operations.

They answered questions such as:

  • How do you prioritize when just getting started with product ops?
  • Does the expectation/ role of product operations evolve as the company evolves? 
  • What is the right path into product operations?
  • What is the ratio of product management to product operations people/teams at your company?

Watch the Full Session Below:

3. Melissa Perri’s Keynote Live From an Actual “Build Trap”

Following the session with Chris Butler, the one and only Melissa Perri, ProduxLabs CEO and bestselling author of “Escaping the Build Trap” joined our booth from her very own “build trap!” As you can see, Melissa’s been busy, not only building products but perhaps a new workspace as well!

During her session on building an outcome-focused strategy, Melissa shared a wealth of insights from her views on what it means to be outcome-focused, the importance of the CPO role, how to advocate for product ops, core tools for product management, and much more.

One of our favorite takeaways from her session was her explanation of the difference between outputs and outcomes: 

One of the big misconceptions I think people don’t understand is that yes, you need outputs to get to outcomes. So we can’t forget about the outputs. But the whole idea about outcome focused product management is that the outputs are a means to an end. They produce an outcome. If you’re not keeping your eye on what you’re trying to achieve, it’s really easy to get into the trap of just building and building and building.

So outcome product management is really about understanding deeply what the business goals are. How can you achieve them through helping your customers achieve their goals? Then, how can you tie the strategy together while monitoring if you’re reaching your outcomes? How close are you in achieving your strategy? How far? What do you need to do to get to the next level? That’s really where outcome-focused product management goes from.”

Melissa Perri, CEO, ProduxLabs

When discussing the role of a product manager, Melissa Perri shared:

“Product management is about really optimizing this value creation system, which is that you’ve got customers on one side that need customer value and businesses that provide the value to the customers through products and services. As product managers, we need to figure out how to optimize both pieces of that. How do we maximize customer value, and in return get business value? To do that, you need to have a really deep understanding of your customers. You have to be very aligned on your business goals and tracking towards them. You have to have really tight feedback loops to understand what’s going on.”

Melissa Perri, CEO, ProduxLabs

Last but not least, having just joined our Board of Advisors, Melissa Perri explained why she is excited about Dragonboat’s product portfolio management platform:

Watch the Full Session Below:

4. Jackie Orlando’s Tips for Building Product Ops

How do you build product ops from scratch? For many newly hired Product Ops Directors, this is the million-dollar question.

Jackie Orlando, Director of Product Ops at Tealium, shared her journey of building product ops from the ground up and partnering with Dragonboat for Tealium’s product portfolio management needs. 

Here are some of Jackie’s best tips for getting started with product ops:

  • Don’t take on too much at once, focus on your burning problems to solve first instead of boiling the ocean.
  • Work with your leadership to identify the big rock problems you want to solve first and prioritize them, and then tackle one thing at a time. 
  • Try not to introduce too many tools at once and try not to have multiple tools that solve the same problem.
  • Don’t be afraid to evolve your team charter over time. As you go, your areas of focus are going to mature along with your team. 

Jackie realized she needed the right tooling to help her:

  • Create a single source of truth
  • Enable smarter outcome-based decisions
  • Enhance visibility
  • Streamline status updates
  • Increase cross-functional transparency

The search for this kind of solution led her to Dragonboat. 

“Dragonboat was the only solution I could find that actually focused on the outcome-based decision element. Allowing us to tie our feature ideas directly to our company OKRs and product objectives, which then tied into our ability to slice and dice things and create reports that give senior leadership visibility into where their investments are being made across the org.”

Jackie Orlando, Director of Product Ops, Tealium

Jackie’s views on the importance of product ops and its purpose of generating a single source of truth for the product org echoed what Melissa Perri touched upon in her session:

“The time it takes to figure out ‘Is this the right decision?’ is usually what slows down organizations. If you can’t make a decision, you can’t build something, you can’t get it out there, you don’t make money. So that’s where product operations becomes really important. It makes that go faster.”

Melissa Perri, CEO, ProduxLabs

Watch the Full Session Below:

5. Product Manager Mavens Explaining How They Make Difficult Trade-Off Decisions

After Jackie’s session, we were joined by Raz Carcoana, Senior Product Manager, Pie Insurance, Dalia Vazquez, PM consultant, and our new VP of Product, Tijana Dwight, for a lively discussion related to the changes and trends to watch for product managers in 2022. 

The audience asked, “How do you go about making difficult tradeoff decisions?

Raz first replied, acknowledging that thinking about where to spend one’s time and resources to make the greatest impact is one of the most challenging parts of being a product manager. He explained, “Until you do it, you can’t measure it. And if you can’t measure it, you don’t know if it’s working or not. And so, you have to put your best foot forward.”  He continued, 

“At the end of the day, it comes down to stakeholder alignment and getting everybody to execute at the same time. What you want is everybody on that page, rather than a lot of friction and disagreement.”

Raz Carcoana, Senior Product Manager, Pie Insurance

He clarified that disagreement isn’t bad, it’s part of having a dialogue which is always needed before picking a new direction.  

Dalia Vazquez agreed and added,

“Fail fast! Everyone’s always looking for a magic wand or Wonder Woman’s bracelet. But the reality is, if you work at a startup or small company, everything is a fire. Everyone will tell you, “This is important”. But I’ve found that creating a source-of-truth helps reduce politics, conflict, etc. We ” 

Dalia Vazquez, Product Management Consultant

Watch the Full Session Below:

6. Learning When Product Portfolio Management Becomes Essential

During our last session of the day, Becky Flint was joined by Rachel Weston Rowell, SVP Product & Innovation, Insight Partners to discuss why product leaders should level up from product management to product portfolio management.

They explained that portfolio management is about how to evaluate and allocate various investment options based on desired outcomes. Even if you have one product, treat it as a portfolio, since most products will have multiple components, segments, goals, etc. For outcome-focused product teams, applying the responsive product portfolio management approach means they can adjust desired outcomes periodically, based on the state of the market and business.

Rachel and Becky go on to explain that if you are running multi-quarter, multi-team initiatives, it’s time to adopt a portfolio approach. Here are some of the signs that product portfolio management is the right fit:

  • Scaling R&D
  • Multiple teams
  • Dependencies
  • Competing goals

When asked about how product management and product portfolio management differ, they shared this slide which paints a helpful picture:

Want to learn more about responsive product portfolio management? Get a Dragonboat demo.

Watch the Full Session Below:

7. “I see an elephant”   

Last but not least, here is one more of our favorite soundbites from the day!

When it comes to product management, metaphors and analogies about the role are a dime a dozen. (Especially if you’re on Twitter!) However, Dalia shared her own product management metaphor which doesn’t disappoint:

“It’s like that picture of all the blind men, touching the different parts of the elephant, and they’re all trying to describe it. And the leg, the trunk, everything is important, but the product manager is standing over here like, ‘Y’all are touching only one part of the whole picture. I can see the entirety of it.’

And that’s how I see product management and product development. I see it as an elephant, constantly.

Dalia Vazquez, Product Management Consultant

Thanks to everyone who visited our booth, we were blown away by the positive response to our sessions, the interactions we enjoyed with you, the thought-provoking questions you asked, and so much more!

Congrats to our raffle prize winner, Matt DiBari, Chief Product Officer at SpotHero, who will receive our “Ultimate Work from Home Bundle”!

Don’t miss out on our upcoming events, subscribe to our newsletter in the footer of our website to receive all of our event-related updates!

Did you go to ProductCon? What was your favorite part? Let us know!

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What is Product Portfolio Management?

We’ve observed a puzzling paradox—great product managers exist at market-leading and market-losing companies. So what does it take to build a high-performing product organization that propels companies to wild success? The answer is Product Portfolio Management (PPM).

In this post, we’ll look at the definition of product portfolio management, its evolution, its relationship with product management, and the key elements.

What is Product Portfolio Management?

Product Portfolio Management is the practice of aligning an organization’s product portfolio with its business strategies to achieve profitability. It involves evaluating product performance, identifying risks and opportunities, prioritizing high-value products, and optimizing resources. That lets you make informed tradeoff decisions and balance the product mix among strategic buckets.

Product portfolio management borrows principles of portfolio management from the finance world: 

“Portfolio management is the art and science of selecting and overseeing a group of investments that meet the long-term financial objectives and risk tolerance of a client, a company, or an institution.”

Besides making the best investment decisions, winning portfolio management includes:

  • Allocation to various categories of investments to maximize portfolio yield. 
  • Periodic allocation adjustments based on the goals, performance, and markets.

A successful product organization operates the same. It uses a portfolio approach to evaluate product categories and allocate resources to maximize business outcomes. In addition, it is responsive and adaptive to fast-changing market trends and business needs. 

Next, let’s look at the history of portfolio management to understand how we arrived at the newest evolution—Responsive Product Portfolio Management (PPM). 

The Journey to Responsive Product Portfolio Management

Traditionally, product organizations ran Portfolio Management, which considers each product line an investment option. For example, the Proctor and Gamble baby care portfolio comprises shampoos, powders, and diapers. 

When IT came along, the product line became intangible. But, the need remained to allocate resources (e.g., engineers) to best support customers. That led to Project Portfolio Management, defined as:

“The centralized management of one or more portfolios, and involves identifying, prioritizing, authorizing, managing, and controlling projects, programs, and other related work, to achieve specific strategic business objectives.”
Project Management Institute (PMI)

Project Portfolio Management fits well in a waterfall-type environment. However, this approach became a struggle as digital products grew more complex. Digital products, like Google Search, often appear as a single product from the customer’s perspective. But the product organization for Google Search has many product teams with their own underlying “product areas.” It is a “one-product portfolio.”

In this structure, product portfolio managers face many questions. How do you define categories for product investments when there are no easily separable product lines? How do you evaluate and decide which part of Google Search to focus on? Where should you increase or reduce investment? 

With the adoption of agile product development, Project Portfolio Management, with its pre-defined, fixed-scoped projects, no longer worked. 

In agile, engineering teams work collaboratively with product managers to design better ways to solve customer problems. However, if product managers start working with engineers on all ideas, all the time, across teams, it can become very chaotic and confusing. 

These were the “new” challenges we faced 15 years ago at PayPal during its Agile transformation. So we created a new product portfolio management practice to support multidimensional digital products in an agile world.

This practice is called Responsive Product Portfolio Management (Responsive PPM).  

Traditional Portfolio Management vs. Project Portfolio Management vs. Responsive Product Portfolio Management

Chart showing the iterations of product portfolio management.
The three iterations of PPM

How is Product Portfolio Management Different Than Product Management?

Now, you may wonder, “How does portfolio management interact with product management, and how do the two differ?”

Product management sparks innovation and problem-solving at the level of the customer’s need. In contrast, portfolio management ensures strategic alignment and resource allocation to maximize portfolio outcomes. 

Core product management skills include analyzing customer needs, product discovery, design, planning, iterating, and releasing new product features. Portfolio management skills include strategic planning, forecasting, resource allocation, trade-off analysis, scenario planning, and adjustment.

Chart showing the difference between product management and product portfolio management.

Can Small Orgs and Individual Product Managers Do Product Portfolio Management?

Can a Product Manager apply a Responsive PPM approach, even if they don’t have control of the company’s entire portfolio of products?


Product portfolio management involves managing complexity and delivering the best product outcomes given constraints. Product Managers find themselves doing this already, every day. 

Every product manager leads a portfolio since their product or product area needs to support several goals, multiple segments, and various themes. The emphasis is not on managing the size of your portfolio but on managing your choices.

Watch the Webinar Recording: Replace Your Roadmap with a Responsive Portfolio to Drive Outcomes

Key Elements of Product Portfolio Management

Now that we’ve covered the different iterations of product portfolio management and how it relates to product management, let’s break it down to see what is involved.

Product Roadmapping

A roadmap is a visualization of the vision, priorities, timelines, and work required to meet your goals. Roadmapping helps you communicate your plans to stakeholders and track progress.

Before building a roadmap, you must collect and organize customer insights. These could be internal ideas or direct feedback from customers. If you’re doing a feature-based roadmap, you would work from this backlog of requests and choose which feature to prioritize for a single outcome. However, with outcome-focused roadmapping, product teams can take a more holistic approach to prioritizing features that will drive the best outcomes while considering all the dimensions of the business, customer, and portfolio. 

Remember, customizing your roadmap based on your audience and showcasing varying details is crucial. Indeed, this is the last step of any great roadmap—sharing it!

Present the data in a way that quickly aligns everyone involved and communicates the plan. For example, C-level executives likely want to know if your roadmap is on track and meeting OKRs. On the other hand, a weekly sync with the product team must highlight the details of each Epic, visualize dependencies, show progress percentages, and display statuses. These are two very different roadmaps, but both are equally important.

Portfolio Management

In addition to the PMs’ focus on their individual roadmaps, product leaders and product ops need to align and manage the entire portfolio—multiple products and their dependencies. To do this successfully, connect your long-term vision with team execution. The most successful product-centric companies do this by starting with corporate-wide business goals and identifying where to invest resources to achieve meaningful results. 

Next, set objectives that span multiple business areas and link them to the corporate strategy. You can even connect objectives and key results (OKRs) to your initiatives and roadmaps. By linking these, you prioritize initiatives for the relevant OKRs based on how much they contribute to each objective. 

During this step, you’ll want to anticipate trade-offs to understand the opportunity cost of prioritization decisions. Roadmaps cover the what and when, but it’s vital also to include the “how” and “what-if” scenarios during resource allocation so you can respond to the inevitable changes driven by the market.

This framework is how outcome-driven organizations operate. It becomes an internal pulse and guides teams to prioritize what to build next while keeping everyone aligned through planning, resourcing, and progress tracking.  

Some organizations also like to analyze existing product portfolios using frameworks like the Boston Consulting Group’s Growth Share Matrix or GE/McKinsey Matrix. The BCG Matrix organizes products based on their relative market share and growth rate into four categories, with “cash cows” being products with low growth but high market share. In contrast, the GE/McKinsey Matrix looks at the competitive strength of the business unit compared to industry attractiveness.

Outcome Delivery

The key to delivering outcomes is to ensure your strategy aligns with the company’s overarching goals. Outcome-driven teams constantly decide where to focus, choosing the features that will provide the most impact and greatest outcome. They prioritize and re-prioritize diligently to keep their work connected to the near-term focus and long-term vision.

Today’s industry-leading organizations allocate resources between multiple dimensions, outcomes, and timeframes. They apply the rock, pebble, and sand technique to best manage their company’s product portfolio. In doing so, they can also move forward with their big, strategic bets and continue to innovate and transform.

The last element to delivering outcomes is continuously evaluating progress toward your goals and responsively adjusting. For example, you should adapt if the team is over-achieving in one goal and underperforming in another. No need to wait for the next “planning cycle” to make a change. That is the beauty of outcome-driven product management—the ability to respond, adjust in real-time and keep every effort focused on your goals. 

The Benefits of a Responsive Product Portfolio Management Approach

Product portfolio management is the product-centric company’s key to combating chaos, misalignment, dependencies, resource bottlenecks, and other growing pains.

While there are a few “flavors” of PPM, we recommend following the Responsive PPM approach:

  • Produce outcome-driven initiatives that are iteratively built, tested, and learned from or validated before the next iteration.
  • Encourage a bottom-up workflow that empowers teams and leaders to make iterative and holistic decisions toward achieving their OKRs.
  • Allow executives to adjust and reprioritize in response to changes in execution, available resources, and external factors.
  • Tie the strategic and execution cycles to the rhythm of “Align, Allocate, and Adjust,” ensuring everyone moves in the right direction and speed. 

Rather than planning only once a year, Responsive PPM is the rallying drumbeat for an entire organization. Responsive PPM lets agile, product-centric organizations maintain agility regardless of size and scale. 

Are you interested in learning more? Then, join the fastest-growing community for product portfolio management and connect with industry colleagues at

nium dragonboat product portfolio management case study

Four Portfolio Risks Every Product Leader Must Address

Every product leader faces four portfolio risks to achieve business results (OKRs) and minimize opportunity costs.

  1. Strategic misalignment risk – leads to failure in achieving goals
  2. Prioritization risk – leads to siloed decisions and local optimization
  3. Delivery risk – leads to preventable product and business losses
  4. Opportunity risk – leads to slow response and declining competitive position

Let’s take a deeper look at how to mitigate product portfolio risks.

The Strategic Misalignment Risk

Successful product organizations rely on empowered teams to create the right products. However, as an organization scales, multiple teams and functions may be involved in building products. As there are many ways to achieve the same goal, the Strategic Misalignment Risk increases exponentially with each new product manager or team added. As illustrated in the example below, one team can build a bridge while the other digs a tunnel. Both aim to solve the same goal of connecting the two sides, but the strategies are misaligned.

To address the Strategic Misalignment Risk, product leaders need to create a Strategic Framework to guide product decision-making throughout the organizational levels.

The framework starts with creating strategic alignment at the portfolio level. This is called top-down strategic alignment – where leaders define goals and collaborate with the next levels to define the high-level strategies to achieve these goals. The flow of strategic direction on the right side of the diagram below shows the strategic alignment from the top down. Teams can also come up with strategies to achieve these goals. Strategies are aligned at the portfolio/ executive level. This bubble-up workflow is illustrated on the left side of the diagram. Regardless if leaders or teams come up with the strategy to achieve certain goals, the alignment must come from the top level to ensure clear guidance to the rest of the organization.

3 Horizon strategy and execution in responsive PPM

In today’s fast-changing environment, the focus and strategy change more frequently at the portfolio level. The strategic intent often gets lost or misinterpreted. Adopting a source of truth for the Product Portfolio is essential to enabling continuous and up-to-date context for everyone within the organization.

The Prioritization Risk

“As a product team, we prioritize features using RICE and then draw a cutline. Everything above the line goes to Engineering. And everything below the line needs to be deferred.”

You mean this is not a good way to prioritize?

This feature scoring type of prioritization approach should alarm you. It is a telltale sign of Prioritization Risk that may lead to siloed decisions, local optimization, and disjointed user experiences (aka product by org chart). Prioritization risk is the result of isolated prioritization without the big picture product portfolio context.

Feature factory – scoring may lead to local optimization

Compliment feature scoring with the following to address Prioritization Risk:

  1. Connect features with customers and goals
  2. Assess allocation across goals, customer segments, and other products
  3. Collaborate with the engineering team on different product solutions with different resource needs. Try manual workarounds/ non-product solutions temporarily to solve customer problems iteratively
  4. Evaluate portfolio scenarios and trade-offs
real time allocation with prioritization
Dragonboat Forecast Module – Allocate + Prioritize + Scenario Analysis

The Delivery Risk

I quit “company X” because their product teams over promise and under deliver. I had to deal with many angry customers and my angry sales teams. It was a no-win situation.

– anonymous Chief Revenue Officer

While engineering teams practice agile iteration, there are often needs to deliver product commitment. Not just for customers, but for the planning and execution of downstream, cross-functional teams who are involved in bringing the product to market.

Delivery risks are often due to dependencies, poor estimation, loss of resources, interruption, tech debt, or a sheer misunderstanding of the current progress vs target completion date.

To address Delivery Risk, product leaders need to

  1. Spot and account for dependencies during roadmap planning (aka quarterly roadmap planning)
  2. Assess and allocate appropriately for tech debt as part of portfolio planning
  3. Allocate for production support and unplanned interruptions to reflect the true capacity for feature development
  4. Track progress and trends to spot the risks early (e.g. leverage the smart alert feature in Dragonboat)

Leverage an integrated tool like Dragonboat that connects planning with execution and adds progress tracking, smart forecasts, and alerts to reduce the effort and skillset required in managing delivery risk.

The Opportunity Risk

Congrats, your released feature achieved its goal. Do you reduce its allocation in the next planning cycle? What if another product area is under-performing? Do you move additional allocation to this area?

If you don’t adjust portfolio allocation from time to time, you introduce Opportunity Risk.

During the current roadmap iteration, product teams may also see new opportunities arise, problems emerge or features get delayed. Their roadmaps need to change. The speed of roadmap changes introduces Responsive Risk.

Often product teams rely on skilled program managers to juggle spreadsheets, lengthy meetings, and back and forth “scenario” planning to Tetris roadmap changes.

In today’s fast moving world, an integrated, smarter tool is needed to reduce manual work and speed up decisions.

Product leaders need an integrated portfolio platform to lead their organizations. A platform that facilitates the best practices of product management, enabling effective decision-making at the individual PM level and across the portfolio.

– CPO, Feedzai

In Summary

To address the four key portfolio risks and ensure successful product portfolio management, product leaders should adopt:

  • A strategic framework that addresses strategic misalignment risk.
  • An integrated prioritization process that addresses siloed prioritization risk.
  • A smart planning and tracking process that addresses delivery risk.
  • A portfolio scenario process that addresses responsive risk.
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5 Tips on Scaling a Product Organization for Growth

As a company grows, scaling a product organization becomes exponentially more complex. Should you double down on your existing product and market with richer offerings and more price tiers? Or should you expand to an adjacent market? Perhaps a new use case for a new market segment? Or create a new product? How should your team organize and plan? Could a product ops role help eliminate silos and improve team efficiency? When a company grows from under 100 employees to 300, 2,000, or 10,000+ employees, each stage faces unique challenges.

In this post, I’ll share learnings from scaling a product organization and building and rebuilding engineering teams at companies like PayPal, Shutterfly, Bigcommerce, and Feedzai during their various scaling phases.

Specifically, this post will cover five topics:

  1. When it’s time to review the “scaling problem”
  2. How to organize your product teams
  3. How to apply a portfolio approach to managing product
  4. When and how to adopt a multi-tiered planning process
  5. Why you need a source of truth for everyone, not only product teams

When Does the “Champagne Problem” Start?

“Looking back, we should have addressed scaling way earlier,” said Eddie Machaalani, co-founder of Bigcommerce,

When should you start thinking about scaling?

When your engineers can’t fit in the same room!

– Eddie Machaalani, Co-founder of Bigcommerce

That’s at about 20 engineers or 4 scrum teams. Sharing and collaborating between teams starts to require more deliberate effort to prevent silos and loss of context.

In addition to the size of the team, the scaling challenge becomes more prominent once a company reaches product-market fit. Customer growth creates use case expansion, making it much harder to prioritize. And it’s also when the tech platform needs to be revamped.

Some founders call it the “champagne problem.” Nevertheless, it’s still a very hard problem.

One of the first things to tackle is the structure. Not the HR-related structure, but the structure of collaboration nodes. Consider when it makes sense to introduce a product operations manager to “PM the PM experience.”

How to Organize Your Product Teams

There are a few ways to organize your product and engineering teams:

  1. System component/ product area, e.g. web, mobile, data platform. This matches well with engineering expertise.
  2. User journey – such as onboarding, using, and reporting.
  3. Persona (aka vertical) like merchant, consumer, operations.
  4. Goals/ outcomes e.g. growth, retention, scalability, innovation.

All of these structures have pros and cons, especially if you stick to one type for too long.

In an output-focused organization, the stable team is highly valued to reduce the learning curve and increase delivery velocity.

In an outcome-focused organization, the internal mobility and flexible team is more valuable in bringing new ideas and learnings from one part of the organization to another.

Sean Kane, VP of Engineering at Upwork

Additionally, initiatives are often carried out by multiple teams, regardless of how the teams are structured.

What I’ve seen work best is a hybrid structure with more periodic changes.

For example, organize by goal/ outcome with the semi-permanent structure of component/ system. This way, goals are aligned within the same “temporary” team while there is still some technical/ domain continuity for fast ramp-up.

At Bigcommerce, initiative teams were built with engineering pairs (semi-permanent structure by component/ system) and adjusted every 1-2 quarters depending on the needs of the business and product.

How do you decide on the formation and size of these initiative teams? This takes us to the product portfolio management approach that every scaling company needs to adopt.

How to Apply a Portfolio Approach to Managing Product

“Portfolio? We only have 1 product.”

– Anonymous Founder

If you still think a portfolio approach only applies to companies with “many products”, check out the responsive product portfolio management framework.

A digital product is often a “bundle of multiple products” for different personas, or to achieve multiple goals. For example, a marketplace has buyers, sellers, and other players.

The responsive product portfolio management (Responsive PPM) approach allows you to categorize all the things you want to do as a portfolio of investment categories. You’d allocate various amounts of resources to these buckets at different times to produce the best outcome for your company within that time frame.

To learn more, read about the rock, pebble, and sand portfolio management analogy.

In a responsive portfolio framework, you may also evaluate your product portfolio across multiple dimensions including goals, products and customers. For example, the goal dimension of the portfolio has buckets like growth, retention, cost; and the product dimension of the portfolio has buckets like core expansion, new use case/ solution, new market, etc.

The portfolio approach has an influence on how your teams are structured. At Feedzai, when there were about 20 product engineers, we broke the product team into a Platform team for the original core product and multiple solutions. This gave each of the product leaders a focus on their “permanent” structure. At the same time, goals were set and adjusted from time to time, due to the nature of the market, product, and business.

As soon as you hit product-market fit, the product team should start discovery on the next product or extension, as it takes time, trial, and error to find one that may work.

– Saurabh, Chief Product Officer (CPO) of Feedzai
responsively adjust allocation scaling product organization
Adjust team size based on product performance

An effective product organization assesses and adjusts the team structure periodically to balance the needs of the portfolio. This leads to the next topic – tiered planning.

When and How to Adopt Multi-Tiered Planning

Many people think problems such as chaos and misalignment are unavoidable growing pains. However, they are often addressable problems.

Eddie Machaalani, co-founder of Bigcommerce

First, leaders need to adjust their perspectives as the company grows. At a smaller company, leaders commonly keep tabs on the company through day-to-day scrums and one-on-one meetings. As the company grows, it’s necessary to have separated vantage points.

A scaling company has 3 levels of vantage points – the executives focus on the long-term vision, while the teams focus on bi-weekly sprints. The VPs and directors are the ones to align both executives and with each other on how to achieve the long-term vision before they can empower their teams to move towards the direction that the whole organization is moving towards.

3 Horizon strategy and execution in responsive PPM

These 3 levels of focus naturally lead to the 3 levels of planning cadence – annual, quarterly, and bi-weekly.

And they are not just once a year or once a quarter type of events. Just like scrums have daily stand-ups after sprint planning, quarterly planning is accompanied by weekly or bi-weekly check-ins.

Aligning on the strategic focus (also called “bets” or “big rocks”) in the annual cadence is critical to setting the direction of the company. It could be growth via acquisition strategy at Shutterfly, or growth via expansion in LATAM at PayPal. These strategic bets set the direction for quarterly initiatives.

The quarterly planning focuses on both the breakdown of bets and the adjustment of the focus for the next cycle based on outcomes from the previous quarter. Allocation to various portfolio buckets is evaluated as a guideline for prioritization within each bucket. High-level resource needs and dependencies are identified and addressed before they hit teams to prevent “agile madness”.

Why Do You Need a Source of Truth for All, Not Only Product Teams?

Product and engineering teams tend to be more self-reliant and don’t mind using spreadsheets and decks. But this approach is not only time-consuming, it delays the access and accuracy of information to the rest of the organization. Chaos and misalignment happen when product teams “hoard” information. Oftentimes, features were delayed or even canceled while marketing, sales, or support continued with their motion unaware of the change. Or the same feature may have different names in different decks, emails, or other channels causing major confusion across areas.

The first change all scaling companies should make, if not one already in place, is having product operations develop a source of truth on the product roadmap. What will be available, when, who can be reached for more information, and what’s planned but not committed yet are all important for the organization to know.

The speed of access to information directly correlates to the speed and quality of decision-making.

The Scaling Mindset

In personal growth, there are phases of the leadership pipeline: managing yourself (individual contributor), managing others (manager), managing managers (director), functional managers (VPs), business managers, etc.

As the company grows through its first 50 people, there are ICs and managers. When it hits 100+, the managers will need to grow into Director level roles, and some ICs would have to grow into manager-level roles. By the time the company hits 300 people, another round of collective growth is needed for directors to grow to VPs, and managers to directors, and so forth. Because each of these leadership level transitions requires significant adjustment on perspective and focus, scaling is difficult.

Process, organization, cadence, mindset, and tooling are all critical parts of scaling. At key stages of a company’s scaling, leadership must adjust all of these parts to work well in the new phase. While a tool does not solve all problems, a good tool enforces best practices. A good agile tool helps the engineering team to practice agile, whereas a good Responsive PPM tool helps the product organization to become an outcome-focused responsive organization.

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