Women In Tech — Becky Flint, CEO of Dragonboat
Becky Flint is the Co-Founder and CEO of Dragonboat, a smart platform to help companies accelerate product execution — combining what you intend to achieve (goals for your roadmap), when you want to do, and looking at your resources (team and skills) and other constraints, to find the best way to take the product features to market.
In this episode of Women In Tech, by Plato, we talk to Becky about her career and some of the lessons she’s learned building products at companies like PayPal and BigCommerce.
How did you come up with the idea of Dragonboat?
Dragonboat is, in my friends’ words, Becky in a box! In my career, I have worked very closely with product management and engineering management. I’ve been both sides to help teams to figure out goals, how to work together, how to take in customer and market demand, how to organize people and projects so that we can take a product to market fast.
However, this was done historically on spreadsheets. At the time I was at Paypal, leading Paypal global expansion. Later on, I led program management and delivery at Shutterfly TinyPrints and then in two more companies at Bigcommerce and at Feedzai.
All these companies were going through a very fast growth period and we had to constantly adjust and juggle between our priorities, our market needs and then teams, hiring and organizing. It has always been very chaotic for us to work really well together.
That’s where the name of Dragonboat comes through: to be a coordinated, aligned team so that everyone row along the same direction to achieve our goals. After many spreadsheets and a lot of work, I realized there are no tools to actually help us to do to it intelligently.
So we built Dragonboat not only as a tool but provides a process and a method on how to align, coordinate and organize teams together during growth. It has baked in our experiences and intelligence.
Walk us through the early days of your career and your journey.
I often look at people’s career and it’s fascinating to me. When I look back at my own career, I realize now it’s a very unusual journey. I actually have a background in medicine and almost became a doctor but I decided to change my career because in those days I could not become a surgeon as a woman.
So I decided to change career and came to the US for business school. At that time, I was already a full grown-up, I was 26 and had $500 in my pocket. I barely spoke English, I went to school here trying to learn business and finance.
That was the first era of the Internet in the year of 1997. Everyone was in a technology startup and I was interested, excited, intrigued to find something so new and fascinating.
So I joined a startup and worked for free because I was a student and couldn’t really work for pay. But I just really enjoyed working there helping companies to build websites.
That’s how I got into tech and one thing led to another through the waves of the dot com growth and dot com bust and I luckily landed into PayPal.
So PayPal was a new chapter of my career. I started as a project manager and then was the first member of the team in charge of growing PayPal’s international expansion. PayPal was growing so rapidly I learnt so much and my responsibility grew bigger over time.
When I started the international expansion at PayPal as the project manager, we were only available in five countries. Six years later PayPal was in more than 200 countries and I had gone from individual contributor to program manager to senior manager and leading a team in four countries.
That really gave me a different perspective on growth and the challenges coming along with it. After leading program management, I’ve had a few other roles at PayPal like leading product and building a new planning and roadmap execution framework for PayPal. Eventually, I ran out of new things and I decided to move onto a smaller company for a new challenge.
I joined a company called a TinyPrints which was acquired by Shutterfly and worked there for a while, helping the company to integrate a smaller team (100 people team) into a bigger organization. And chance led me to another growing company in San Francisco called Bigcommerce.
That took my startup days of building a website to a whole new level — with eCommerce, payment platform, apps, shipping and all sorts of things. It really helped to take the learnings from PayPal growth to help that company to establish a way to scale and grow and ship product across the globe.
The next journey I went to was at Feedzai, a very interesting company, a lot smaller in scale (when I started there were only 150 people). The company was really on the verge of a growth breakout, which it did because it grew from about 150 to 350 people in less than a year.
And I guess there’s a brand new challenge: how do you balance the two competing forces of building the platform while also delivering a product? How do we focus on a roadmap? How do we deliver? How do we structure our team?
It was a great journey where I applied what learned through my earlier career at PayPal, through my experience at Shutterfly, through my experience at Bigcommerce.
The experience all helped in the next journey but eventually, it came to a breaking point of “hey, we cannot do it like this. I know how to build and scale roadmaps, but we cannot do it with the spreadsheets.” And this led to the birth of Dragonboat.
You couldn’t become a surgeon as a woman. What are some other challenges you still have to face to this day?
When you look at the individual contributor level, maybe not in engineering teams but in UX, design, product, quality, there are fewer women but not significantly a smaller number. But the higher you go, the smaller the number.
After a few years climbing the ladder, I started to realize everywhere around me were guys. It is challenging from that perspective: the viewpoint can be very different, the style can be very different, and opinions that get carried out and are discussed are definitely different.
I have learned to be more cautious on how I put my viewpoint out in a way that is more explicit, more direct. Sometimes I repeat myself more often to be more comfortable in my own communication style.
I think that there are a couple of things that I don’t want to stereotype one way or another but, at least from me and a couple of my friends’ perspective, I feel like it would help us more if we prepare more. It seems like quite often when we’re in situations like meetings, brainstormings and the other sessions and debates, it is often more forgiving if a male counterpart has a point that wasn’t fully valid or thought through versus a female who may not be a fast thinker or didn’t have as many facts and figures. That tends to be a little bit more likely discounted.
So I think that basically requires us to do a lot more homework: “Hey, what do I need to prepare for those?” I really built that habit and if I don’t prepare for those sessions, I would be slightly disadvantaged compared to, you know, typically guys. That’s the interesting thing I noticed but it’s more common in meetings.
What are some other differences in terms of your roles and responsibilities going from IC to Manager to Founder?
It’s a very good question. I think that, interestingly, there are more similarities in these roles than I originally expected. However, there are also very conscious decisions I make in different roles, meaning, the broader my responsibility is, the less I get to do things I really like.
I think in my happier days in my career was the time when I was actually a product manager or a project manager because I actually got to get my hands dirty working with the team, spent a lot of time on things and not worrying about other things.
As I grow higher in responsibilities, to director and VP and CEO, I realized I don’t get to do a lot of fun things. I have to make conscious decisions.
If I do something more fun, quite often, it does not work correctly in my job. That really should be my team’s opportunity to do things that have a more direct impact and what I need is to provide the framework to support them, to enable them.
The framework should not be only within our own teams but also more about how our teamwork with another team, how our organization works with another organization. And these are a lot more impactful and sometimes it’s a little bit of a learning curve and requires effort to constantly remind myself that my focus is different.
My focus now is enabling my team, enabling my organization in building my company and enabling our partners to be able to achieve more together.
For other people coming in and just starting out their career, what advice do you have for them?
It’s interesting that when we look back at a career, we easily see the trend but it’s harder when you actually go through that.
For the most part, there are actually ups and downs on the journey.
The reason I’m saying this is, for example, in the earlier days when I came to the US, I had to start everything from scratch, right? I not only had to learn the language just to get by, but I also took an unpaid internship, basically working for a company where everyone else is, on paper, more junior than me, but that’s not the point.
My point is I would learn something new that I didn’t know. And in this way, these people were more senior than me. That kind of step happens in many ways. When I was at PayPal and working in the program management field for a while I became very successful and led large teams.
But then I went to the product field, I actually stepped down because I became an individual contributor again. So I actually had to go write specs, worked with the team and stepped back even though the level is the same but the role itself is deeper and a more IC-like role.
That actually happens also as you move from company to company. So I think to have a mindset of “I’m doing something really new to me. No matter how experienced, whatever level I am, this thing is new to me and therefore, I’m willing to take a step down for the next step up.”
I think that is a very important mindset for me, at least, to be able to progress both in terms of the position and in terms of responsibility. How do we make a path forward? It’s not one straight line.
You are also a mentor at Plato and you give advice to mentees. Can you tell us why you decided to join as a mentor at Plato and describe that experience?
A few things made me decided to join the Plato community.
One is I feel like everyone lives in a bubble, that’s a good thing. But that’s also a bad thing because we don’t really get to experience new things and perspectives. As we grow up in our career, we start to form a network with people and a bubble. So, to me, being able to interact with new people in different places is something interesting to me.
The second part is about mentoring people: it’s something very important to me personally and professionally. I truly believe in it. As someone who went from an individual contributor to a leader, I’ve been mentored directly and indirectly — sometimes I reach out, sometimes people just mentor me without even knowing it. I benefited a lot from that.
I take that with me for my team. For every individual, every single member of my team in the past, including those who do not work with me anymore, I always told them, in my first 1:1, that it’s very important for me to develop people and it’s my responsibility to mentor you in ways that are helpful. It not only pays forward but it is just also good for everyone.
The third part is very interesting: mentoring people in some ways has the reciprocating effect as well. I am also being mentored by the people’s new perspective with questions I didn’t think about. For that reason, I enjoy that as well.
So these are the couples of main things that contribute to me being part of the Plato community and fairly active on it.
Want To Get Mentored By Becky? Find Her On Plato!
Plato connects engineering managers and PMs with experienced mentors and tech leaders from top companies like Google, Lyft, Netflix, and more. You’ll get to have group mentoring sessions alongside peers, and private conversations with mentors like Becky.
To get a taste of Plato, sign up for a group mentoring session here — http://community.platohq.com
Looking to mentor, or know someone who’d make a good mentor? Apply here — https://www.platohq.com/become-a-mentor
