September 30, 2021

Matt McGowan on his passion for developing teams

Madeline Perretta

What is your role?
Sales Leader. I manage a team of Plaids providing our West Coast customers with outstanding service.

Describe what you do in a few sentences.
I lead our Startup and Mid-Market segments for the West. A portion of the Account Executives on my team are focused on our startup segment, which is essentially any business between one and five employees. These companies are often very new to market and in many cases, are pre-launch and pre-funding. 

The other AE’s on the team are focused on our Mid-Market segment, which includes companies that are slightly larger. Both of these are absolutely essential customer segments for us where some of the most exciting financial products are being built.

How does your work impact people’s financial lives?
We’re working with businesses who are often brand new to market, or not even yet to market. My team is lucky enough to be working with the companies pushing into new territories of the financial services world. We see the most unique and creative products that address so many unmet needs for consumers and businesses - everything from financial management for separated parents to fractional ownership of physical assets like sneakers and wine, to small business loans for the self-employed. These unique services are directly changing and improving how people interact with their money and their wealth. It’s really fantastic and fun to play a small, but meaningful role in that. 

Plaid’s mission is to unlock financial freedom for everyone. What does this mean to you?
Building on the above, to me, that means that however someone could possibly choose to interact with and allocate their money, they likely now have an avenue to do it. Plaid unlocks choices. Moreover, Plaid has enabled numerous business models that weren’t in existence 5 years ago. At best, they were reserved exclusively for the high net-worth individuals or those with great credit scores. The playing field has never been more even, and Plaid really is playing an outsized role in enabling that capability. 

What do you love most about working at Plaid?
So, I’m unlikely to be the first person to say this...ha...but the people. I genuinely like the people I work with and have felt this way since joining Plaid when we were 80 employees to now being over 900. Obviously, it’s a little harder to meet every single person at this stage, but I truly believe that Plaid has consistently done an amazing job over the years of bringing people into the company who are both smart and friendly.

I also feel that it's notable that my answer and my thought process on the people hasn't changed in the four years that I've been here. Smart and friendly have been the consistent two traits that I see in all the people that come into Plaid. And I think those traits make for both a positive and productive culture.

What sets Plaid apart from other places you have worked?
As someone on the sales side, the amount of demand for our product is unique in my career. The typical archetype of a salesperson is someone cold calling prospects, sending tons of emails, and trying to get people to take a meeting with them - and we definitely do our fair share of outbound account development - but here more than anywhere else I’ve worked, companies in our space are aware of Plaid and in many cases, come to us to have a conversation about how we can help them. We’re extremely fortunate that through our product, we’ve created an amazing brand that resonates with both developers and enterprises, and because of that, we get to have interesting conversations every day.

Okay, let’s go back before Plaid. 

Describe your journey into sales. How did you choose that career?
As a History major in college, I didn’t have a ready-made path like someone in accounting or finance. I honestly didn’t have any idea what I wanted to do, but I put my resume on - and to my surprise,, Monster’s biggest competitor, was the first company to contact me. They were hiring folks in Chicago to sell companies on putting their open jobs on the internet, as opposed to listing them in the newspaper. Crazy idea, right? It was the only interview I went on and I got the job - so I took it. I had to make 125 cold calls per day to companies under 30 employees and my territory was Ohio and Kentucky - half the businesses I talked to weren’t even using email yet, so the idea of putting their job ads on the internet instead of the local newspaper was laughable to them. I told myself I was going to give it a year and see how I liked sales - four and a half years later, I was still at in a field sales role in our Silicon Valley office and working with some of the largest software companies in the world.

I gained so many fundamental skills for selling during those times, which I still use today! I definitely learned how to deal with rejection - over, and over, and over..ha. I feel really grateful for that opportunity because it helped lead me to where I am today. 

How did you learn about Plaid?
Prior to Plaid, I worked at a seed-stage startup that was essentially a payroll platform, but for 1099 workers, so think independent contractors and freelancers. We started looking at Plaid to help us get customers up and running on our platform faster. Previously, the process was very manual - it would take several days for us to validate the business and perform fraud checks on payment transactions. Plaid was going to automate all of that, so I was personally excited about Plaid as a product and what it was going to do for our company at the time. We ended up actually getting acquired before we implemented Plaid, but Plaid’s value was clear to me from that time forward.  

What made you want to work at Plaid, and how did you make it a reality?
When it was time for me to find my next thing, I was dead set on working for a company whose product had tangible value that I could understand and sell, was early enough that there was still plenty of foundational work to do on the go-to-market side, and was in fintech - Plaid checked all of those boxes. 

To apply, I went to LinkedIn and sent a cold message to Paul Williamson, who was the Head of Sales and is now our Head of Revenue. I'd love to say my cold message worked perfectly on the first try and he offered me a job on the spot, but no. A few days and continuous LinkedIn stalking later, I was able to get a friend to make an introduction.  Paul was kind enough to grab a coffee with me, then I interviewed with a few other people, and started a couple of weeks later - that was over 4 years ago. 

How has your role evolved over time?
I started at Plaid as an individual contributor - so I was working directly with customers day to day and bringing them onto Plaid. Now that I manage a team, I’m a step removed from those direct customer conversations, most of the time. I still love working directly with customers when I can, but my responsibility is definitely more to enable my team to meet our goals, rather than to influence deals directly.

Plaid is a high-performance environment. How do you unwind?
I have a 3 year old daughter and a baby boy on the way, so it’s pretty full-on even outside of work hours. But when we unwind, you can find us at the playground, at the beach, doing sidewalk chalk, blowing bubbles, doing art, and reading lots and lots of books together. 

Also, wine. Every parent earns a glass of something nearly every night, right? I’ve always enjoyed it, but three years ago my wife and I traveled to a couple different wine regions in France and since then, it’s really become a passion. I love all kinds of wine, but some favorites lately include German Riesling, Cote Rotie and Cornas from the Northern Rhone, and anything sparkling.  

I also love to play the drums.

A drummer? Tell us more!
Growing up, I was certain I was going to be a professional musician. I’ve been playing drums and percussion since I was 10 years old -  in relatively formal settings like school bands, orchestras, and jazz bands, as well as with my own garage bands. My first garage band’s live performance was in 5th grade - we covered Nirvana’s “Come as You Are,” “Brain Stew” by Green Day, and even played a few originals. One of the guys in that 5th-grade band is literally a professional musician to this day - he scores movies and has written theme songs for TV shows alongside playing in his own band. Clearly, I didn’t make it that far in the music business, but I still play with friends regularly. In our early days before kids, we played bars and venues all around San Francisco, but at best, we now get together every 6 weeks or so, just to play for fun. 

What are you passionate about?
Related to work, I’m passionate about developing my team into one that’s high-performing. Luckily,  I have amazing folks who are exactly that already on the team. But I love teaching new skills, I love working on fundamentals, and I love helping people get better. I have a long, long list of skills and competencies to get better at myself, so self-improvement is also high on my list. 

Outside of work - being a good dad and partner, music - notably Pearl Jam, Notre Dame Football, White Sox Baseball, and wine. 

What are you proud of?
Definitely the easiest question on the list. My daughter, Finn. She’s totally fearless, outspoken, bold, smart, hilarious, and incredibly loving. She pushes every single boundary that we set for her, which sometimes can be a challenge...ha...but I'm positive that her relentless spirit will be one of her defining strengths as she continues to grow into her own person. I think she's going to give the world a nudge, and I'm excited to see her do it.