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The following transcript has been altered for readability.
Introduction
Josh Berman: Hi, everyone, welcome to today’s Product Ops HQ meetup. Thank you for joining us. My name is Josh Berman. I’m Head of Product Marketing at Dragonboat, and I’ll be your emcee for today’s session. Along with me, I have Alyssa Voss from the Dragonboat team, and she’ll be assisting us on chat if you have any questions. In addition, be on the lookout for some of the great resources and content that Alyssa will be sharing with you as we progress through today’s session.
For those of you that are new to the Product Ops HQ meetup, I’d like to share a warm welcome. For context, Dragonboat’s Product Ops HQ meetup was created to serve the needs of the growing product operations community to meet, share ideas, learn, and grow. We do this by hosting regular virtual meetups covering a wide array of topics like the one you’ll see today. We also do this by providing networking opportunities to meet like-minded folks in the field. One such example of this is the virtual space we provide on Slack where you can ask questions and tap into the communal knowledge of Product Ops pros like yourselves. If you’re not there yet, we encourage you to join us there today.
Josh Berman: What I love about this community is how global we’ve become, and it’s kind of a tradition as part of these meetups to ask you all to chime in on chat and share where in the world you’re located. Product Ops is gaining popularity and influence, and it truly knows no bounds. So I encourage you all to chime in on chat right now and share where in the world you’re located.
While everybody’s saying hi, I want to make a few notes about today’s session. As always, this session is being recorded, and you’ll receive access to the recording via email after the event. Our format for today’s session is that we’ll be presenting and then doing a Q&A session to conclude the event. If you have any questions at any point throughout, we encourage you to share them in the chat, and we’ll either answer them right in the flow of the event or we’ll follow up during our Q&A session to answer them for you. The only ask I have for you all today is that you mute your mics when we have our presenter talking—it can get a little noisy and distracting. Please do respect that.
Before we dive into today’s topic, I’d like to acknowledge that it would not be possible without Dragonboat. Dragonboat is the number one product operations platform that enables product leaders to maximize business impact through effective product and portfolio management. It provides a single platform to manage your entire product operating model. I encourage you to check us out at dragonboat.io.
So now to our main event: today’s session, “Product Decision-Making for Revenue Impact,” will be led by Keoki Andrus. With a product career spanning over 30 years, Keoki excels in creating integrated product strategies and scalable roadmaps. He has a strong track record of building product ROI through go-to-market alignment and product leader development, helping companies achieve a competitive edge. Keoki, I’ll hand it over to you for a brief introduction and to kick us off.
Opening Remarks
Keoki Andrus: All right, well, hello, everyone. It is great to virtually be with you. You know, this question of product ops—it’s kind of this emerging thing. It’s an interesting problem because, like, what is it? And when I talk to people, not everybody’s even aligned on what it is, but we’re all in this role or we’re working with it. I kind of see product ops as having a couple of different roles. One is helping with product practice to help normalize it because we need to be able to scale it and make it work, you know, from person to person. And then what does product practice contain? Well, it contains setting up strategies, making decisions, and then executing those strategies. Product operations supports all of that.
What is the most important part? It’s usually the part you’re having the biggest trouble with in your organization right now. Today, I’m going to mainly focus on that first part: how do you make good product decisions? I won’t go as deep into supporting that decision-making or implementation, but rather the decision-making itself.
Keoki Andrus: To start off, I’m going to tell a little story from my own experience that illustrates how difficult the product management challenge is and how we can approach it. I know that I’ll say some things today that sound very definitive, like “this is the way it is.” Of course, there are exceptions to everything. Instead of dancing around these edge cases, I’m just going to say things as they are. If you disagree or think it’s obviously wrong for some reason, we can discuss it, or you can decide, “Keoki’s just not talking about that edge case.”
As we go along, feel free to throw questions into the chat. We don’t have to wait for Q&A at the end. We can take questions in real time, and we’ll just roll with it.
The Story: Turning Around a Struggling SaaS Company
Keoki Andrus: So, here’s my story. In 2016, I was invited to lead a product for a SaaS company that had been going through a rough time. For two years, they had not shipped anything material. This was because they had a leader who was very charismatic but also created a lot of churn. Morale was terrible. My first month there felt like I was playing therapist as I went around meeting people. The company’s win rate was 12%, despite having a decent pipeline—that’s horrible. There was a lot of finger-pointing between functional groups.
When I walked into the sales department, it felt like a morgue. People were slumped over their desks, and the energy was just so negative. On top of that, the technology team had frequent outages due to all the churn happening, which led to more churn—losing business. That’s what I walked into. It was a really bad situation.
Immediate Steps for Change
Keoki Andrus: To address this, we decided to define something we could ship quickly—something that would make an immediate impact. We needed to boost morale and prove we could do something. At the same time, we had a growth market we wanted to enter: big customers. Despite having spent millions of dollars building a pipeline, our win rate with these big customers was zero. We’d get all the way through the bidding process but lose every deal.
To start, we shipped something quickly to prove we could execute. Then, I started implementing some simple human principles. Did you know that smiles and laughter raise effective IQ? When people feel good, they perform better. I walked through the sales department four times a day, smiling and chatting, getting people to laugh.
Next, we gave functional groups a voice in decisions. We also built choice models to figure out gaps in our offerings for both core customers and growth segments. We developed our first roadmaps, implemented processes to enable on-time delivery, and invested in improving reliability.
Keoki Andrus: What happened next? Within two months, even though we hadn’t shipped much, our win rate increased by 50%. Retention started climbing. Eventually, we became the leader in reliability for our industry. The thing I’m most proud of? I went to the executive team and told them, “We’re going to start winning these deals.” They laughed at me—not outright, but with looks that said, “Yeah, sure, Keoki.” But we did start winning those deals, and soon enough, they became so common that we stopped talking about them. They became part of the business norm.
Sixteen months later, we successfully sold the business in a liquidity event. All of this stemmed from what we did from a product ops perspective: how we made decisions, where we placed our bets, and how we executed.
The Core Job of Product Ops
Keoki Andrus: So, what is our job in product? It’s simple: decide what to build, get it built, and ship it successfully to maximize ROI. But we often forget the “maximize ROI” part. Too much focus is placed on creating roadmaps and collaborating with engineering, but if the market doesn’t know about what we build, what’s it worth?
I like to say, “A feature that no one knows about doesn’t exist.” Our job has three main goals:
- Improve Win Rate: Anything that helps us win more deals.
- Grow and Retain Customers: Ensuring the product keeps customers engaged and reduces churn.
- Achieve Operational Excellence: This includes faster delivery, better reliability, and cost management (e.g., cutting down expenses like MongoDB licenses).
These are the three things that matter. Everything we do should align with at least one of these.
Decision-Making Challenges
Keoki Andrus: Let’s talk about decision-making. One common pitfall is the “Field of Dreams” mindset—“If we build it, they will come.” This belief often drives poor decision-making in product. Everyone assumes they have the key to success: customer feedback, prioritization matrices, the loudest voice in the room. But these are flawed approaches.
Another challenge? Over-indexing on users while under-indexing on buyers. It’s easy to track what users are doing, but harder to understand buyers’ motivations—especially when users aren’t the ones making purchase decisions. This disconnect can lead to a focus on things that don’t move the needle.
Lastly, responding to customer complaints without a strategic lens can create what I call “Frankenstein products.” These are products overloaded with features, added in response to customer demands, but lacking cohesion or a clear vision. While this might help win specific deals, it doesn’t help win markets.
Managing Tech Debt and Operational Excellence
Keoki Andrus: Let’s address the tech debt trap. Have you ever heard someone suggest dedicating 10%, 15%, or even a day a week of your resources to tackling tech debt? It sounds logical—after all, tech debt can slow us down and make development harder. But here’s the reality: removing all tech debt won’t necessarily improve your win rate, grow retention, or make your product more reliable.
Instead, every tech debt initiative must come with a clear business case. For example, if reducing MongoDB costs by 50% could significantly impact profitability, then it’s worth the investment. If fixing tech debt will enable faster scaling or improve reliability in a measurable way, it might be worth considering. But vague promises of future efficiency aren’t enough.
To illustrate this, I worked with a team that saved one developer week per month by refactoring their reporting system. It took three developer weeks to implement, but the ROI was clear within three months. That’s a good tech debt decision. Without a compelling case, tech debt can become a bottomless pit.
The Importance of Metrics and Leading Indicators
Keoki Andrus: One of the biggest opportunities in product ops is defining leading indicators that allow you to measure success early. For example, if you’re trying to improve win rates, track how many sales reps are fluent in the new feature during beta. If adoption isn’t happening at that stage, your win rate won’t improve. Other leading indicators might include:
- The number of mentions in customer conversations.
- Growth in pipeline for related features.
- Requests for information or trials.
By identifying these metrics upfront and integrating them into the initiative, you can make adjustments before it’s too late. This approach applies to all three core objectives—win rate, customer retention, and operational excellence.
Lessons from Success
Keoki Andrus: In one of my previous roles, we implemented a process that ensured 90% of our shipments were delivered on time. At first, the engineering team resisted, fearing commitment. But over time, they embraced it. Within a few years, they were delivering 95% of projects on time, nailing aggressive timelines consistently. Their pride in being part of such a high-performing team transformed the culture and set a benchmark for the industry.
Closing Remarks
Keoki Andrus: To wrap up, remember this: there are no exceptions to the three core goals. Every product investment must align with improving win rates, growing retention, or achieving operational excellence. No feature, no initiative, and no “small ask” should bypass this rule. That discipline is what drives meaningful results.
Audience Q&A
Josh Berman: Thank you, Keoki, for sharing these incredible insights. Let’s open the floor for some questions.
Audience Question: How do you manage expectations around the time it takes to see results from product decisions?
Keoki Andrus: Great question. This is why leading indicators are so important. During the planning phase, I work with product managers to define metrics that we can measure during beta. For instance, are customers engaging with the feature? Are sales reps talking about it? By tracking these early indicators, we can identify problems and course-correct before launch.
Audience Question: What are some tips for managing an outsourced product development team?
Keoki Andrus: Focus on alignment with the goal. Outsourced teams often do exactly what they’re told, but greatness happens when they understand the bigger picture and take initiative. Communicate not just what needs to be done, but why it matters. Encourage them to speak up if they think something doesn’t align with the overarching goal. That level of engagement can elevate their performance and drive better outcomes.
Final Thoughts and Wrap-Up
Josh Berman: Thank you, Keoki, for your time and wisdom today. I think everyone here has gained valuable insights into making impactful product decisions.
If you’d like to get in touch with Keoki, his LinkedIn profile will be shared in the chat. For those of you interested in exploring how tools like Dragonboat can operationalize your product operating model, we encourage you to visit our website at dragonboat.io or use the links shared in the chat.
Additionally, don’t miss our upcoming session in the CPO Series featuring Vanessa Garber, where we’ll dive deeper into the role of strategies and outcomes in the product operating model. You can register for this session through the link in chat.
Finally, for those looking to continue the conversation, join our Slack community to connect with other Product Ops professionals. Thank you all for attending today’s session, and we look forward to seeing you at future events!
Thanks again, Keoki, and thank you all. Take care and have a great rest of your day!
