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July 02, 2018

Jake Stern on starting as Plaid's first New Business Associate hire

Madeline Perretta

Updated on November 19, 2019

Photo by Kevin Hu

You’re in sales. Can you describe what that looks like at Plaid?
I started as the first new business associate. Basically, you’re the face of Plaid for any company, startup or enterprise reaching out to us. I would lead the initial discovery and qualification as well as help smaller startups further along the sales cycle with their integrations. It’s highly consultative. You have to learn a lot about the background of the team you’re talking to, the unit economics of their business, the core product and the resources at their disposal.

How has your role changed since your started?
I was promoted to do outbound sales to help lead the charge to reach out to companies who we'd like to work with. Plaid recently launched in Canada and my day-to-day thus far has been developing new business opportunities there. This is a new function for Plaid and our first launch into another country. My job has involved workshopping the outreach strategy with the head of sales, working cross-functionally, generating pipeline and collecting product feedback.

What excites you about your work?
Every day, the conversations I have require lots of critical and creative thinking. Also, it’s awesome to feel like I’ve made an impact building a sales development function and the beginnings of an outbound strategy for a company like Plaid. When I started, neither formally existed. We have a culture that celebrates bottom up innovation. It has been awesome to feel like I’ve had a direct and permanent contribution to growing our team and the overall business.

What’s challenging about your job?
Explaining what Plaid does. It sounds like a simple challenge, but it’s interesting because we are such a technical solution and we sell into financial services organizations, many that aren't technical. One of the great learning experiences for me has been how to tell our story to different people from different companies who care about different things. Some are focused on data quality. Others care more about conversion or increasing the lifetime value of their customers. My challenge is to identify what companies need, tell our story and work with them to realize how we can help. This is very difficult, but rewarding.

You credit the time you spent in Ecuador between high school and college with inspiring your career trajectory up to this point. Can you describe that experience?
I was lucky enough to have grown up in Palo Alto, but as a kid, it can feel like a bubble. So when I was 17, I decided that I wanted to take a year before college to learn more about myself and explore other parts of the world. Looking for different opportunities to do that, I found a program I liked called Global Citizen Year. It’s like the Peace Corps, but for kids who've just graduated high school. During that time, I became fluent in Spanish and lived with a family of eight for seven months. I was volunteering at a healthcare center and a credit union. It was an awesome experience. I walked away feeling much more globally minded and learned a lot about how commerce and technology could change peoples’ lives. It’s why I decided to study economics in college.

Which you did, at Brown University. How did you apply your experience in Ecuador to your undergraduate education?
The experience in Ecuador evolved into an interest in innovation and entrepreneurship. When I got to Brown, there wasn’t really an organized student community doing things related to that. I joined a club called the Entrepreneurship Program and saw that there was this gap where a lot of classmates wanted to learn about how to start things and collaborate in a structured way. So I started a program called Innovation Dojo. We took applications and ran a semester-long workshop modeled after Steve Blank’s lean startup class, with the goal that at the end of the semester, everyone would work on their own project and then present it to the student body. We got tons of applications and it kind of caught fire. It’s actually still going on at Brown today.

After graduation, you worked on the 2016 presidential campaign. How did that prepare you for your role at Plaid?
I joined the Democratic campaign after the primary in August and I was working as a field organizer. The party parachutes you into a battleground state, sets you up with a bunch of voting precincts and voter data and says, “now you go and organize all this.” I was required to hit certain goals for a given territory by recruiting a team of volunteers. For example: register sixty voters, call two thousand people and go door to door in ten neighborhoods. In its own way, it’s an extremely challenging sales job that taught me a lot about being creative, resourceful and resilient.

Coming off the campaign, what appealed to you about working at Plaid?
Three things: the culture, the team and the role. With respect to the culture, I care about making sure that what I’m working on is good for the world. What’s inspiring about being here is we have a consumer-first focus. It’s something we talk about every day. Being an advocate for the consumer is very much part of our ethos.

On the team, we have great leadership and everyone is incredibly talented and very curious. People also come from very diverse backgrounds, so conversations around the office are always interesting. It’s also a super flat, collaborative environment.

As for my role, I felt like it was a great opportunity to start my career in an exciting job that would teach me a really strong, consultative sales skill set. I also wanted to put myself in an environment that would challenge me to get more technical. That, combined with my interest in economics and fintech, made joining an easy decision.

What is your favorite space inside the Plaid headquarters?
The ping pong table, definitely.

What do you do with your time outside of the office?
This past year, I explored San Francisco. Also, I love riding motorcycles. I got my license right after Ecuador. I go on a long ride every other week or once every three weeks and it’s a big passion of mine. I’m planning for a big trip sometime soon. There’s this road in Iceland. It’s supposed to be awesome. Maybe that's next!

Finally, Jake, how would you describe Plaid in one word?