Career Stories

This VP of Product Shares How to Roadmap Your Career

Yael Barak, the VP of Product at Checkout.com
Yael Barak, the VP of Product at Checkout.com.
| Courtesy of Checkout.com

As a problem-solver by nature—and someone with a never-ending curiosity about the world around her—Yael Barak was meant to be a product manager, a role that hinges on discovering pain points and then figuring out how to fix them.

But that’s not all Barak, the VP of Product at Checkout.com, loves about the work she’s been doing for the last 15 years. “As a product manager, you’re constantly identifying new ways of driving value for customers,” she says. “You’re at the confluence of every business process, driving cross-functional collaboration, and developing life-long skills such as communications, analytical thinking, and empathy.”

Here, Barak shares what she’s working on at the fintech company, why product managers need to be good storytellers, and the importance of owning your own destiny.

What led to your job at Checkout.com, and why were you excited to take on the role and join the company?

I love the payments space and wanted to continue my professional journey with a fintech company that was building payment products at a global scale. I was also looking to join a product organization that had a strong customer-centric focus, and where I could leverage my experience to help grow and develop the team just as much as the product itself.

I got the opportunity to do all of these things at Checkout.com. My team and I work with all functions of the business on a daily basis, we are relied on to develop strategy and build a roadmap to execute on it, and we are the voice of our customers within the organization.

What are you responsible for as the VP of Product?

I am accountable for one of our product pillars. My team and I are responsible for developing the product strategy, taking into account factors such as market conditions, the competitive landscape, and customer pain points. We work with all facets of the business to understand their perspectives on our product, and with other product and tech teams to make sure we’re all moving in sync so that our products come together to provide a great experience for our customers. I also represent Checkout.com at events and conferences, visit our customers, and help develop and mentor other members of the product team.

How is the product organization structured at Checkout.com, and what is the product development process like?

Each product team is a multifunctional unit made up of product managers, software engineers, designers, and project managers. Each team is empowered to work independently and make decisions on what and how to build, and we collaborate with other product teams to ensure that all our products provide a consistent and delightful experience for our customers.

To keep up to date with our peers we have regular product review sessions in which product managers share what they are working on with the wider group, obtain feedback, or validate some of their thinking and analysis. We’re a pretty laid-back group and everyone is approachable and always willing to help out.

What skills do you most value in product managers? What does it take to succeed in the role?

Good product managers are curious, empathetic, and analytical. When considering a problem they seek to understand it from multiple perspectives and come to their own conclusion based on data and research. It helps to be a great storyteller because in the process of solving complex and ambiguous problems it’s critical to craft a narrative that makes sense to different audiences such as buyers, users, and cross-functional team members. A good product manager can explain their product to any stakeholder in a way that is understandable to them. Finally, leadership qualities such as conflict resolution, facilitation, and collaboration skills are also important.

What do you find most important in a company culture and how do you foster that among a team?

More than anything these days I’ve come to appreciate the value of inclusion and transparency. Inclusion means everyone has a voice regardless of seniority or role, and even if we have contrasting views we come to a conclusion respectfully and move forward as a team. Transparency is all about building trust. As a leader I want my team to trust that I have their backs, and I want my cross-functional partners to trust that I’m thinking of their best interest. It’s much easier to achieve this trust when you’re open and transparent about challenges and you involve the team in solving them. What this means in practice is that we have regular cadences as a team where we share product strategy, perform team health checks, and evaluate our ways of working together. Everyone on the team has a voice.

As a woman who has worked in male-dominated fields like tech and finance, what has been the biggest challenge you’ve faced in your career and how did you overcome it?

I’ve been generally lucky to work for organizations where opportunity was rewarded based on merit and performance. When I face a situation in which I feel I’m being evaluated as a woman ahead of a professional, I try to counter factually. For example, when I was a new mother, a former manager assumed that I would want to avoid business travel to stay close to my children. I informed him that wasn’t the case.

I can’t say that there is no discrimination in the workplace, and bias is experienced by other groups as well. My approach is to align myself to an organization that has clear policies and a strategy to address these issues, and to contribute to solving them by setting a positive example.

What advice do you have for other women who are pursuing leadership roles based on your experience and career path?

Don’t be afraid to use your voice and make your wishes and objectives known. I tell everyone (man or woman) that they are the owners of their destiny and that taking chances is worth it when you’re going after something you really want. Don’t wait for a tap on your shoulder to get an opportunity, but rather knock on someone’s door and let them know you’re ready to step up. Ask for feedback on what it would take to achieve your objectives and listen carefully to the answers you get. Then internalize, analyze, and create a strategy and roadmap. That’s right—you can product manage your career, too!

What have been the keys to your success as a leader?

With every year that passes I learn new things and unlock insights. One theme that runs through it all is resilience. There are going to be many ups and downs—in your personal life, for the business, for someone on your team—and you need to be able to forgive yourself for your mistakes, learn from them, and move on. If you extend patience and support to your team they’ll do the same for you.

How do you practice work-life balance?

I like to Crossfit to counter sitting at my desk all day. There’s nothing like throwing heavy weights around and working at the edge of your endurance to get you out of your own head. There’s also lots of learning to be had about stamina and resilience from taking on hard physical work. My working hours can be erratic since I collaborate with teams in multiple time zones, but I protect my daily workout time religiously and I encourage everyone to do the same. We should all work smarter rather than harder!

You’re organizing a dinner party with three people, real or fiction. Who’s invited and what will you talk about?

The older I get the more I want to spend my time with people who have a positive outlook on life, navigate challenges with an optimistic mindset, and generally don’t take themselves too seriously (sense of humor is a must to get in the door). For that reason, I would invite Gandalf the Grey, Ruth Bader Ginsburg, and Terry Fox [a cancer research activist who ran across Canada, despite having one leg amputated, to raise awareness for the disease]. I’d love to get their perspectives on how to find resilience against tough odds and what grounds their determination to push forward in tough times.

Updated 11/14/2022