Women in Tech Podcast: A Behind-the-Scenes Look at Dragonboat

women in tech becky flint dragonboat

Building products has never been simple. Our founder and CEO, Becky Flint, experienced the challenge first hand while building the product portfolio management function for fast-growing companies like PayPal, Shutterfly, and Bigcommerce. She tried dozens of PM tools but found that none supported the needs of an outcome-focused product organization. 

So, instead of patching different tools together, she made her own prototype that solved this problem. Now, 20 years in the making and several iterations later, Dragonboat.io is a reality and our team is growing!

Becky recently sat down with Espree Devora on the Women in Tech Show to talk about her founder’s journey. She tackled questions like:

  • When should you start your own company?
  • What are the biggest challenges of entrepreneurship? 
  • How did you overcome these challenges while starting Dragonboat?
  • What is your advice for women looking to build their careers in tech?

You can listen to the podcast episode here:

The following transcript has been lightly edited for clarity. 

Espree Devora: Welcome back to The Women in Tech Podcast, celebrating women in tech around the world. So excited for our next guest, Becky, coming at us from the Bay Area in California. Hello, Becky.

Becky Flint: Hi, Espree. So exciting to talk to you today.

Espree Devora: I know, I’m stoked to have you here. To kick things off, go ahead and tell us a little bit about who you are and what you do.

Becky Flint: Yes. So, my name is Becky Flint. Today, I am the founder and CEO of dragonboat.io. For those of you who are not familiar with the Dragonboat, it is a purpose-built platform for all outcome-driven product organizations. Dragonboat is new, but for me, it has been 20 years in the making, so we can go deeper-

Espree Devora: What? 20 years in the making. Wait, no, let’s stop, let’s jump into that now. How is it 20 years in the making? Tell us.

Becky Flint: So, it’s very interesting, I never thought about starting a company to build something like Dragonboat. When I joined PayPal it was fairly small, most of the product managers, almost all product managers can fit it into one conference room. You can imagine how small we were. I was brought in to help lead a global expansion. As you can imagine, expanding PayPal to other countries takes a lot of work. There were a lot of challenges and really the rise of something today we call product operations

Long story short, as PayPal was growing very rapidly, we’ve gone through a lot of growing pains, a lot of challenges. I had to build lots of internal tools and spreadsheets and I couldn’t make it work. Then, finally, I learned a process called product portfolio management. And that essentially led to the tooling that became the predecessor of Dragonboat.

Later, I went to a few amazing companies and joined them and they were pre-unicorns or small unicorns like Shutterfly, Bigcommerce, and Feedzai. Then eventually they went through the journey and it become a unicorn then a public company. 

As a part of the process, the need for Dragonboat was all over the place. I looked at all the tools and found all the things I could find in order to patch everything that we needed together to scale product rapidly while maximizing outcomes. And what I found was there was no boat, there were only pieces! 

Later I became a consultant, and I was recruited from company to company, where I brought along this “boat” which, was still, at the time, a suite of spreadsheets. Finally, I thought, “Hey, if I had to scale something like that, maybe this is the tool, it’s the product I have to build.” 20 years later, there you go, meet Dragonboat.

Espree Devora: That’s crazy. And while you’ve been building, what would you say is the biggest obstacle you successfully overcome in building your company?

Becky Flint: I think startups are facing three key turning points or challenges. 

One is, do we have a problem? If there wasn’t a problem, obviously there would never be a company. So I think the problems were really well understood. 

And then the second part of that is, do we have a product to solve it? 

Then the third part is how can we iterate and improve on it? 

I would say the third part is the lucky part of my journey. I was able to start to test out and try out a product fairly early thanks to people I met in my career and through my network of the people I worked with. 

Regardless of how great intuition is, as an entrepreneur, you still have to hit the road and get people to use your product. It was really helpful to be able to get the product to some of our early customers along the way.

Becky Flint

Espree Devora: One of the things that are really important to you that you shared with me before the interview is building a strong team. Tell me a little bit about your perspective on strong team building.

Becky Flint: It’s a little bit complicated, so let me go take one step back. Meaning that when we think about a team, quite often we think about the people we work together with. So a lot of times they say, hey, I’m in marketing, I have a marketing team, I’m working with my team together. If you are in product, you are working with an engineering team, you have a scrum team, you work with them together. So that is obviously really, really important to have a strong team in that sense. You work with them day in and day out.

Then beyond your team or pod, you have a team that’s not yours. It’s important to be able to work with an extended team to be successful. 

So, in the earlier days working at PayPal and later on in other companies I worked that, as well as eventually getting to Dragonboat, we recognized this. I had a small team when I got started, but I needed more talent and skills, and resources from other areas in order to succeed.

How do I build an extended team and extended network? So how do I find advisors? How do I find partners? How do I find some of the consultants and contractors, they’re all my extended team. And I get to partner with them and leverage a small part of their time. 

Building a strong core team plus an extended team that can help you fill in the gaps of the business’ needs is super important for your startup’s growth.

Becky Flint

Espree Devora: When did you first become interested in technology? Working with a Goliath like PayPal, which became your future. When did that journey start? Were you a little girl or at what point did it start for you?

Becky Flint: Yeah, it’s interesting. I didn’t really fully utilize my education so to speak. I fell into technology. I actually came to the U.S. when I was fully grown from China and I came here for business. I went to Business School in San Francisco in 1997. So for some of you, if you are older, you’ll remember that was a time that web went all out. 

I was in business school and I took a finance major concentration. Next thing you know, the dotcom boom was happening, there’s a lot of startups, all my students and everyone’s just working at different tech companies. 

And then I thought, “Hey, I better go find some real work experience.” The next thing was so exciting. I was working with customers, designed products, and learned to code. And all of sudden I became a tech person. I was like, forget about having an MBA, forget about finance, this is so much more fun. That’s how I started to get into tech and then even started another, like a little startup company trying to do a B2B exchange for a computer manufacturing product.

Then it was all fun, exciting. And guess what? Next thing you know dotcom burst. So then I had to go back to the “real world.” Then I started to work, this is the time where my MBA in finance started to rescue me. I was able to find roles in some of the financial companies. I was in Wells Fargo for a while and then at Schwab for a while. Next thing you know, I heard about PayPal. I was like, “Oh cool. This is tech and it’s also finance.”

Espree Devora: Wow. That’s so lucky. Wait, keep going. I’m just blown away that, because you had that combination of background, PayPal made sense but at the time it was just yet another name on a list, it wasn’t PayPal at the time.

Becky Flint: No, no. It was a small company. It wasn’t really that big of a name so I left really nice job at Wells Fargo to go to PayPal. In some ways also very lucky because I live in the South Bay and Wells Fargo’s in San Francisco, and PayPal’s in South Bay. I said, “Hey, it is a tech company. It does FinTech” I realized finance is great, but it’s just too stable and not a lot of changes, and tech’s much more fun. So yeah, that’s what happened.

I was very, very lucky. And the PayPal team was like, “Well, you don’t really have a lot of experience and maybe you should come in as a junior project manager.” I was like, “I just like this company.” I didn’t care about my job title. I could take a higher-level role but I like the company. I thought it was really cool. So I joined the company, it was just a good time. 

Espree Devora: Because life is an adventure. And we should always just be partaking in the adventure and not so caught up in metrics like finance, vanity or whatever it may be and make sure we’re truly enjoying the process of life.

Becky Flint: Right. Exactly. If I had joined PayPal 10 years later, I would never have had an opportunity to build a portfolio management process across the whole company. That just does not happen to someone at the level like not VP, right? It requires many levels of influence across the organization. 

Then that was also another interesting story because speaking of raising your hand and solving problems, I was leading the international expansion, taking PayPal from country to country. It’s amazing. Think about it. Launching PayPal in Australia, launching PayPal in Portugal.

Espree Devora: I can’t even imagine like five, you said five product managers in a room when you started. Was that right?

Becky Flint: All the product managers fit in one room. 

Espree Devora: I mean, that’s just nuts. How big was the staff count when you started versus what is it around today?

Becky Flint: I can’t remember how big it is today, but when we started, I think maybe a couple hundred engineers.

They had a lot of business and marketing and customer support. But you think about the core product development, product managers and engineers. It was really small. 

Espree Devora: It’s crazy. Such a cool life experience. One thing that I’m really glad that you brought up was your MBA. Because one of the questions I wanted to ask in this really interesting career journey you’ve had is how much has going to school, not just MBA but your university and the MBA helped accelerate you as a tech professional?

Becky Flint: I think it has tremendous importance for me, in terms of in the tech industry, because I didn’t come from the US. So that’s like, if I hadn’t come here for MBA, I wouldn’t even be here, I would be in different countries. So that itself definitely is pivotal in terms of my journey. 

And the second part is when I went from MBA to tech, it gave me a different perspective than the people purely in tech. Because I’m more than just writing code. I didn’t know how to write code, but I can translate the concept, the business, how users could use it, how that makes sense to the user and translate it into code.

Then I learned to code. I think having a sense of the business concept, the P&Ls, the positioning, the messaging, all that stuff is tremendously helpful especially today. Everyone needs customer empathy. 

Espree Devora: The most annoying thing to me about the pandemic, how was it every single company was like, “Oh, now we have to care about our customers.” I’m like, What do you mean? As though this is a new novel idea, you should have been doing this before any pandemic. Why is this now the marketing angle to care about your customers? It’s… Yes, customer empathy to the max.

Becky Flint: I think yeah, in some ways that’s really more of the level of competition. In some ways, the pandemic really accelerates a lot of things into being digital. This also means information is a lot more available and accessible to everyone. That means the competition is much, much stronger in every aspect. And I think a lot about how this impacts the global hiring market.

I’m in the Bay Area, working with all the Silicon Valley companies and stuff. 

There used to be an advantage to living in the Bay Area in terms of starting a company, having a network, etc. Today, that is dissipating very quickly. You can talk to anyone on Zoom, access people and capital; everything is more readily available to everyone. 

Becky Flint

Espree Devora: Let’s circle back to Dragonboat, and then I want to get more into the lifestyle of your company and of your profession, but Dragonboat specifically for everyone listening, who are the customers for Dragonboat? Who should be like, “Oh my gosh, I’m so glad we know that Dragonboat exist?”

Becky Flint: Dragonboat is a platform for the product organization. When I say product organization, it’s not just for product managers. 

Just like sales is not just one person who goes to sell something, there’s always teamwork. So, Dragonboat is the core for supporting a product team. But the product team works with engineering, the product team working with design, marketing and sales, all that. The product teams also work with each other.

In the past, when people tend to think about product teams, like I’m a product manager working with engineering. I can launch and iterate and then just magically, things happen. The reality is today, as soon as you hit a product to market and have customers, you realize you have to work with a lot of people. Dragonboat’s a platform where the product team would be the driver or the hub, but that also helps everyone else interact with the product team.

The feedback, requests coming into the product team, so you have some understanding of what customers want, tied to business goals and outcomes and metrics you have tied. That will help the product team together with the input of the customer, create your product ideas, roadmaps and so on. 

And product teams also have to work with each other so that we don’t have our islands. And because a product is actually built across multiple teams and finally it can be delivered through engineering. Once we put it on to the market, the go to market team has to know what we are building, what we’re shipping, what things are. So, that is the core of it… You can almost think about it, it’s a boat where the part of the organization that is product-related runs, but where everyone also is part of it as well.

Espree Devora: What’s the impact? What’s the solution? Every company is created in order to create the solution. So, now we have product managers signing up for Dragonboat, and then what is the solution in their life?

Becky Flint: One is that product managers need to make the right decisions. It takes a lot of effort, not only in product things and also in being able to communicate and plan and track. So at Dragonboat, the number one thing is to make a lot of busy work go away, so we automate a lot of activities that need to happen for product managers. The second part of that it’s enabling faster and more accurate information to everyone else involved in building product. Meaning, customer success will know what’s going on and the marketing team will know what’s going on. What we plan on the roadmap, being able to put feedback into the system so that we can actually make decisions better.

Dragonboat enables the collaboration of the product team with each other, with the cross-functional teams, and then with stakeholders in a way to best deliver product. 

Becky Flint

Speaking of customer empathy, Dragonboat also allows you to have more stakeholder and internal team empathy as well. So they can deliver the product that drives value and does not increase overhead on everyone.

Espree Devora: There’s so many people listening right now who have thought about taking the leap like you have, working for a company and then creating your own company and being a founder. What drives you to continue to be a founder rather than work for someone else’s company? 

Becky Flint: Right. I think it’s very funny that if you are sitting there saying, “Hey, I want to start a company.” Then I think that’s just not the right time, because you didn’t have a burning problem you have to solve. 

So I started a company two times in my career, in both cases there were burning questions. Let’s use this one as an example. I wasn’t going to start Dragonboat. I really enjoyed seeing a company grow and helping the product team. I loved being able to create products, being able to drive value and sometimes turn around the companies that were struggling to scale. 

Then I decided to start Dragonboat because one, I realized I’m solving the same problem from company to company. And there had to be a better way.

And two is, there were no other options. If I can find other solutions that can solve the problem, even if I’m passionate about the problem, I would go for them. But at the time, nothing stood out. Looking back on my career, I say, “Hey, if I never chose to work for a company and didn’t happen to fall into an amazing company like PayPal,  I wouldn’t be where I am today.” So, had I chosen to start a company at that time, my career would be different. 

If you can learn a lot and meet great people when working for someone else, go for it! You don’t have to say, “I need to start at a company,” for the sake of it. But if you say, “I have this problem, I’ve been trying out various solutions but I haven’t been able to solve it yet. It’s just so painful.” Then, I think it’s time to start a company.

Becky Flint

Everyone says, okay, starting a company is not easy, it is hard. It is so true because, as a founder, maybe 5 or 10% of the time I spend is truly doing the things that I wanted to do. Versus when you work in a company, if you’re in a good role, you spend 60, 70, or even up to 80% of the time on things you want to do and you’re good at you enjoy doing. 

Starting your own company as a founder, you have ambitious goals and you have to do everything, which often means the opposite of what you actually enjoy. 

You do all these other things. It’s not always the most productive, but you have to do it. I think I’m very lucky to have had a lot of support along the way, but it’s very, very hard for sure.

Espree Devora: And in the early days, how did you sustain it? Did you raise money, was it self-funded, was it profitable right away? What was your journey in igniting it and then fostering a team and making sure you’re not losing your mind?

Becky Flint: It is a combination of all of them. So, I self-funded partially from my own savings. And I was also very lucky when I left my last role, I was working with the co-founders and CEO, CTO and then they saw how a properly run product org can change the company. So they invested in me and our company early on, so I’m very, very grateful to them for taking the risk in such an early stage when you didn’t really have a product. Then also I did a lot of consulting which helped with the cash flow.

I didn’t pay myself for two years, that also helped. I used a combination of contractors and consultants. Then we started as a remote native company, we never had an office and I had teams globally in the beginning. So that helps us with the cost, with a lot of access to talent. 

Today, everyone can start a company, covid already made remote work the de facto. But back in the days, it was a competitive advantage. So knowing how to find people to work with and knowing how to work with the people remotely is key.

Espree Devora: 100%.

Becky Flint: I mean, it cut our costs by at least half.

Espree Devora: 100%. My first business partner is one of the co-founders of Box, the file sharing company. When we were building, there was no WordPress. There was no easy way to code. I was very lucky that he knew it all and then he would tell me, I remember it was so cool. 

He would tell me what coding languages, I should be on the lookout for. So I would go to meetup groups with all these developers and I’m not a developer. And they were like, “What are you doing here?” I’m like, “I have to know. I have to know how all these things work in the benefits.” And I was just super curious. 

I’m glad you brought up your savings and then also your past work, help fuel your company. The reason I say that is when I raised money for my company, my investors said, one of the reasons they trusted funding me is because I invested in myself and that showed them how committed I was.

Then a second note is I just met with a company in the past week. They were profitable within I think, two or three months. I’m like, “Wow, that’s so unusual. How’d you do that?” He’s like “The company that I was working for became my first customer.” There’s no one way to build a company, and every single part of your journey and choice that you make could be something extremely beneficial that you would’ve never thought of. It’s so cool.

You really care about women succeeding and you have some amazing advice to give them as they build their careers in tech and possibly become founders or grow the companies they have now. What would some of that guidance be?

Becky Flint: Well, first of all, don’t think of yourself as a woman. First, you think of yourself as a human being. You can do the things you can do, put your agenda on the side. I think that would really help a lot. 

Yes, as a society, we need to help and then we need to provide more opportunities for women. But my mom is a mechanical engineer. And when she went to school, she was one of the 300 people in her class, the only woman. She never thought of herself as a woman versus all the men. She was just like, “Hey, I’m here. I’m a student of engineering and I’m going to be an engineer. There’s no question about my gender.”

I think it was super helpful for me to think about myself as an individual and I can do amazing things and I can put in my effort. I think the first thing is to help each other out. But I really just want to think about us as individuals who can contribute value and not think too much about that. 

Espree Devora: I got into tech through my dad. And he would take me to business conferences and all this stuff. I never noticed I was the only female. I just was a person interested in tech around a lot of other people interested in tech. And I do think the more we self-classify, we may end up putting limitations on ourselves that we don’t need to put there.

Becky Flint: The second part I will say is thinking about it either both life and a career is a journey. There’s no direct line from A to B that you have to take what is coming at you that seems like a good opportunity, learning and growing. 

A prime example was going from an MBA in school and then going to tech startups, because I think there was a lot of activity going on. A lot of things are new, look so exciting. It looks like the future. But the same thing for PayPal, when I went to PayPal, I took two steps down.

To grow in your career, do things that add value, even if it’s not in your job description. Have an eye for seeing problems and then try to solve them.

Becky Flint

But remember, you collaborate with the people who are the “owners.” You don’t just go ahead do it. That’s not good. 

And then always bring good people along with you. When I had a mentor, I saw her not only think about the things in her area, but also think about how her area could expand to help a broader audience and the broader organization. And that’s where she mentored me to give me visibility and perspective on thinking that way. I think that bringing people along, it’s so helpful. The key thing is when you bring people along, you bring the network, you have a different perspective and ultimately everyone wins. So the tide is rising high.

Espree Devora: I love that guidance. One thing that I was also thinking about this week as a leader is when I respond to something, am I reacting or am I responding with confidence from my boundaries? I notice whenever I feel that someone is doing something negative to me or something like that, I stop and I’m like, okay, people could only take as much as you allow them to take.

And I have power over who I say yes to who I say no to, or how I negotiate. And so, how can I show up in a more powerful way that isn’t an attack on either part. Like no one’s attacking me and I’m not attacking anyone else, I’m simply sharing my boundaries. 

The reason why I bring that up is I think the more I surround myself with empowering people and focus on being an empowering person, the more clarifying energy I have to really embrace my boundaries from a positive uplifting spirited place, not like this like dark scarcity based place. 

Does that make sense?

Becky Flint: Yeah. I think that we humans have the rational part of us and also the emotional part. And quite often we’re naturally having an initial emotional response and the rational part of ourselves, will say, “Hey, you know how we want to handle this in a way that’s calm and cool.” It is the right thing to do, but then also over time, takes a lot of energy because you have to do it twice.

So, by choosing unconsciously, surrounding the people and others on the way that they are seeing and act in a way like more calm and then more, I want to you is the word outcome. But it’s really positive outcome focus versus complaining, blaming, negative energy.

Espree Devora: Yes, that.

Becky Flint: Then also you don’t have to do things twice. You just do it once and naturally say, hey, we have a problem, how do we solve it? It’s much better say, why is this happening? That’s like a same problem, different attitude. But if you always hand up with the people say like blaming or whatnot, you’re just very draining

Espree Devora: You said it so much better than I did, that. Last few questions, quick-fire questions.

Becky Flint: Okay.

Espree Devora: What is your favorite book? I’m making you choose?

Becky Flint: Not favorite, but a recent book I liked is EMPOWERED by Marty Cagan.

Espree Devora: And this is a selfish question because I’m such a nerd, your favorite mobile app or software website aside from Dragonboat.

Becky Flint: Calendar.

Espree Devora: Oh yeah. Which calendar do you use?

Becky Flint: Just Google Calendar because our team all use that. 

Calendar isn’t screaming for your attention. All the other apps want your eyeballs all the time. Calendar is there when you need it, running in the background.  I really like that. We all know we could not live without our calendar. 

So, sometimes I think hey, Dragonboat is like that. It’s something running in the background, it enables you, but doesn’t require your eyeballs on it all the time.

Espree Devora: It’s such a good point. We have so many listeners. If there’s one thing that we could do to support and accelerate your success, what would that ask be? And it can’t save the world because so many of my guests always say something that’s to serve other people. So it has to be to serve yourself.

Becky Flint: Well, if I was to serve myself, it would be something say, hey, if you want to grow your career and truly make an impact on other people’s lives, you should check out Dragonboat. 

Because we exist, not as a tool to try to take everyone’s time and energy away, we exist to help, to give time and energy back to others. 

We have lots of opportunities to grow.  To anyone who has a desire to make an impact, I really welcome and encourage you to apply. We need designers, product managers, engineers, marketers, customer, success, sales talent, and more.

Espree Devora: Awesome. Thank you so much for hanging out with the Women in Tech Podcast!

Kalei White

Senior Marketing Manager and Team Rower at Dragonboat
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