Jack LaMar on working with prospective Plaid clients along every stage of the sales funnel

Describe a day in the life of a mid-market account executive.
No two situations are ever the same. Sometimes, a prospect is super technical and has a good understanding of what Plaid is and what we do. In those situations, I’m more of a trusted resource or guide; I confirm or deny their assumptions and steer them toward the correct products. The other side of the coin are prospects that have heard of Plaid but don’t really know what we do—they just think there could be overlap. Those are fun conversations to have. I get to know their business and brainstorm solutions. I get to be much more consultative. I'm not necessarily trying to sell to them; I make suggestions, and they take it and run with it.

What do you like about your job?
I love a prospect or client that's tackling a new financial problem. Last quarter, I worked with a company that’s helping small businesses raise funding through private bond offerings. So, instead of taking a loan from the bank, you or I could buy bonds in, say, a mom-and-pop doughnut shop and get a return over time. I also like working with more established businesses on ways to modernize—the ones that recognize that the financial industry is changing.

You’ve been in four different sales roles since you joined the firm. How did you manage that?
When I joined Plaid, I actually took a step back in title. The idea was to get in where Plaid had an immediate need and then find opportunities to advance. I was fortunate to see that come to fruition. I think that’s because Plaid does a good job of looking at merit instead of strict trajectories. And of course, growing the company from something like 65 people to 417 presents a lot of opportunities to prove yourself.

What makes Plaid a great company to work for?
The c-suite doesn’t sit in a tower out of reach of everybody else. If you have a question, it's flat and open; you can go talk to anybody, which was definitely not the case at some other companies I’ve worked for. And nobody here is above having fun. It’s a lighthearted environment that’s also really serious about work.

What’s one way you and your coworkers keep it lighthearted?
I play on Plaid’s soccer team, which is a lot of fun. Plaid is in a corporate league, so we compete against 20 other companies in the area. We have a rotating crew of about 15 or 20 people at Plaid, and whenever new hires start, we promptly encourage them to sign up for the team.

How would you describe Plaid in one word?
Determined.

Why determined?
It applies to the individuals at Plaid and Plaid as a whole. Everybody here is determined to do well, and as a company we are determined in our pursuit of mission. It’s like there's this light at the end of the tunnel that we're always striving for, but we also understand that, if and when we get there, we will just move it farther away and keep going. Everyone's determined to have an impact and contribute incrementally to that growth. And when you have 417 people all doing that, that really drives the company forward.

What drives you forward?
Energy and self-competitiveness. Growing up, my parents had me play many different sports—soccer, volleyball, lacrosse, basketball, football, water polo—to help rein in both, and I think being so active and having a million things going on actually helped train me to focus when I needed to. I still rely on that skill at Plaid. We're a very fast-growing company. There's a ton to do. But I’ve learned to really zero in on the task at hand, even if that means ignoring my email for hours at a time while I power through a project, so that I don’t get overwhelmed, and I don’t spread myself too thin. That’s one of the challenging parts of working here but also the most exciting. I don't think I would enjoy working at Plaid as much as I do if we didn't have so much going on.

Out of high school, you were recruited to play volleyball at UC Santa Barbara, where you pursued environmental studies. Why that course of study?
When I was a kid, my parents’ jobs were tangential to environmental studies; I was always around public planning, government relations, and things like that. I wanted to do something similar, and I wanted to have a positive impact on the world. That was the motivation.

Where do you think your desire to have a positive impact originated?
I used to be really into punk rock. As I began following different artists, I realized I had no idea what the heck they were talking about. So, I started researching the issues behind the music, and that exposed me to the altruism of environmental politics.

A leg injury ended your volleyball career, which caused you to stumble academically and led to your decision to take a leave of absence from college. You then worked at a law firm, then an environmental firm, and, eventually, you went back to school to finish your degree, this time studying economics at Oregon State. What motivated you to go back to school?
I was in a weird spot with my work. My career was starting to take shape, and I was able to get some great positions without having a degree. On one hand, I felt like I could probably continue to progress, but I knew not having a degree would be a block at some point. More than that, I didn’t want to feel like I had been defeated or walked away from school, so the main motivation was personal. It’s a little hard to explain. Basically, I wanted to prove to myself that I could do it.

How did you balance being a full time student with working eight hours a day?
Pretty much no social life and a total lack of sleep. Honestly, it was rough, but with the experience I had gained since my first attempt at college, I was ten times more prepared and disciplined enough to succeed. I had to plan out my week, commit to a schedule, and stay focused on the goal at hand, even if it was months or years away. Breaking everything down into smaller pieces made it much more manageable. Otherwise, I would have been totally overwhelmed.

How did you ultimately get into tech and sales?
My first foray into both was at a recruiting software startup based in Orange County founded by a bunch of ex-Google people. I had decided environmental consulting wasn’t what I’d thought it would be, so I took a job there as an account manager. And then the day I started, like 10 minutes after I showed up, the head of sales pulled me into a room and said, "We think that you would actually be really good at sales, and we need somebody to start our sales development team. Are you okay with that?" And that's honestly how I got into it. There was not a ton of thought put into it. It was a yes or no question presented to me right after I started my new job.

Why do you think sales is the career that stuck for you?
Sales aligns with my team-oriented background. We have a number we want to hit as a team, but I also want to make my individual goals. The nice thing about Plaid is that it’s not an unhealthy sales environment like some other places. I think we've done a really good job of creating a true team atmosphere, where your goal is to do what is expected of you but also to make sure that you're helping other people around you get better.

How else does sales at Plaid compare to sales elsewhere?
At Plaid, you are challenged a lot more intellectually. With clients, you have to go deeper than what you would at most other sales positions in tech in the Bay Area. It's enough to keep you stimulated and interested every single day.

What are your interests outside of work?
It sounds weird, but one of my favorite things is doing nothing but doing it somewhere. When my wife and I went on vacation to a small town in Mexico, I loved sitting in the town square and watching people and the things happening around me. I really enjoy being an observer wherever I am.

Why do you think that is?
I go through my day in my own head, absorbed in thoughts of self. It's rare to take a moment to really see other people. It’s a reminder that I am not the center of the universe. Consciously detaching from the self-absorption helps me keep things in check. I think it's important to notice that there’s a whole world outside of us.

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