Operator Spotlight: Growth @ Plaid
All Things Venture #063
Hola Everyone, we had some technical difficulties last week that resulted in this article never actually hitting yall’s inboxes. Sad. But we got things figured out, and I’m excited to share this new column. BUT. Before we get into the article, I want to share an update on a previous company I've interviewed, Medley. Medley is run by Jordan Taylor, a fantastic founder (and friend) who is doing the work to build a membership based community designed to help all of us reach our personal and professional goals. The Medley experience is awesome, and I would genuinely recommend it to anyone who is A) looking to meet new people in an authentic, genuine way B) anyone looking for a like minded support group to honestly talk about, and work through career and personal challenges. I was part of the first membership cohort that began in 2020, and I regularly keep up with peers (S/O Strat) from my group.
Jordan and I were catching up for breakfast last week and she mentioned that they’re accepting application for their 2022 member cohort. I told her I’d share the news in my next All Things Venture article, and here we are. Am I broadcasting one of my friend’s startups to the world? ABSOLUTELY. Why? Because startups are 1000x times harder than you think, because I want to help founders like her everywhere and in way possible, and because I genuinely believe (given what I know about some of you amazing readers) that some of you will find Medley’s experiene extremely valuable - just like I did.
Learn more about them here and/or read the original interview with Jordan (Medley’s CEO) here. (And no for anyone who asks or wonders, I’m not getting paid for this)
Aaaaaaaanywaaaaaaays -
Today’s article is a fun one. It’s part of a new column I’m calling Operator Spotlight. I originally started All Things Venture with just one goal in mind, to help share the stories of early stage entrepreneurs, and over the past few months - as I’ve gotten to speak with 100s of founders - I’ve also realized there’s another group I should highlight as well - operators. Early stage operators are just as important to the early stage startup ecosystem as founders. You can’t scale to 1,000 employees without first getting to your first 10 employees, and those first 10 employees will play an outsized role in the development of an early company. So think of these Operator Spotlight articles as a window into the startup world, an opportunity to hear directly from the people building, what their role is like, why they enjoy it, and how they ended up there.
I’m all about sharing stories, learning in public, and contributing in a positive way to the tech/venture ecosystem. My hope is that someone will read one of these articles, take the plunge on joining a startup, and absolutely knock it out the park. It might be wishful thinking, but it’s worked for me and it can work for you too. So with that in mind, I’ll shut up and let’s dive right into our interview with Mary Caballero who is on the Growth team @ Plaid.
Mary! Great to have the opportunity to interview you and share your story, could you share with the audience a little bit more about your background, what led you to want to join Plaid and leave Goldman? Because they're obviously two totally different institutions. And I'm sure they attract two totally different sets of people.
Yeah, definitely. So, I joined Goldman Sachs out of school for a fairly cookie cutter reason, but I have absolutely no regrets about working there. It was, it is, a great place to start your career. It's a place where you can pick up those softer skills, like, how to be professional, how to work hard, how to prioritize, and there's so many amazing people to learn from. I was on an investing team at Goldman, and while I enjoyed investment management, the asset class we were investing in didn’t garner a ton of interest for me. That’s largely what drove me to start to look elsewhere. There were a couple of things I wanted to change about my job at Goldman; it's an old, structured institution, with so many levels, at the end of it, it was quite a hierarchy. With that top of mind, I was super excited to get somewhere smaller, so that I could have a role where I owned more of my day-to-day. So deciding to go big versus small was one decision in the fork in my road, and then another fork was finance versus elsewhere, which, probably because I went to Stanford, elsewhere meant Tech.
Pretty quickly I realized being at a small company was important to me, and I was interviewing at smaller funds, as well as small tech companies. I naturally found through the process that I was more excited about a tech role; I was so excited to interview at the tech companies, work on the case studies, and research their companies, whereas the finance stuff, and maybe because I was ingrained in it day to day, was just not something that I was excited about anymore. So, it was this very natural progression of figuring out what I did like about my job, what I didn't like about my job, and then going through the interview process and talking to people across the tech and finance sectors to figure out where I wanted to be and what I wanted to do. I had a friend at Plaid, so I feel very lucky that I had someone that I could reach out to and talk to. But it was a very long process of you know, what do I want? And where can I find that?
Yeah. And for the readers, so they have context, can you describe your role at Plaid?
Yeah, absolutely. I am on our account management team, and with Plaid’s B2B software product, most of our clients are tech companies. I work really closely with our customer base to do a lot of different things as account managers at Plaid own the customer lifecycle post-sales. We work with our clients to help them get launched, we make sure they have top-notch integrations, and we collaborate with them to find opportunities where Plaid could add value elsewhere in their business. We work with clients to understand if they have new products that they want to launch with us as well as vice versa, do we have new products that we want to partner with them on. We also work on other commercial opportunities and renewals; it's everything from product questions to technical implementation to contracting. We wear a lot of hats.
What was the most challenging aspect of switching from a big institution, like Goldman, to a fast growing startup like Plaid?
I think giving myself work was just a new concept because, when I was at Goldman, I received work from other people; I never picked which funds to interview or which analysis to run. That was not my responsibility. Whereas now, I am the main and sometimes only point of contact for these clients. And so if they weren't actively asking me for something, it was a moment of, okay, how can I make my role valuable? Like, how can I be valuable to them [my clients]? It was a big mindset shift away from, let me do everything on my to-do list, to let me create my own work and make sure I'm adding value where I can.
One of the great things about startups for people in our age demographic is that they can really accelerate your career. How have you experienced that at Plaid in terms of just getting more autonomy, ownership, and also visibility to management?
I think one of the bigger reasons that I was interested to work at a small company is because at my prior job, I found there were very static rules around promotion in a formal and informal sense, like titles were one thing, but responsibility was (and is) so much more important to me. And so now, what's been so cool at Plaid is that so much of it is merit based. It's, “You crushed it as a startup account manager? Perfect you're moving on,” and for me personally that happened. I went from working as a startup account manager to a strategic associate account manager; I moved to work with fewer customers as well as customers with a higher monthly spend. And since then, you know I didn't get promoted in like a week or immediately, but I got promoted again. And so now I'm working with customers at the next revenue threshold. It's really like you can run as fast as you want, and startups, like Plaid, they'll keep up with you. They're like, “Okay, it's time for promotion, it's time for that next level” And for me, it's been within account management, because that’s what I'm interested in.
What do you think you've been exposed to in your career at Plaid that you wouldn't have been exposed to at Goldman?
That’s a good question. I think I've just been given so much responsibility that I wouldn't have gotten as quickly at Goldman. In my role, as the main point of contact for clients, we usually work with PMs, but you also get a lot of exposure to product leads, CPOs, or CTOs. And so, I get to work closely with the CPO or the CTO of pretty significant Fintech companies; I get to collaborate with someone who is extremely successful in their career and I get to hear their take on the lending space or Fintech as a whole. The exec exposure and learning from others has been amazing, and of course there's a ton of similar excellent talent within Plaid too. But, learning externally has been really cool. And a perk to being on the client side for sure.
One of the funny things about your mid 20s is like, it’s hard and fun at the same time, because you're in this process of discovering yourself and what you want and the life you want to build. How has your startup experience played into that or informed that to a certain degree?
Yeah, I think it's given me a lot of confidence. I think something that I was struggling with a lot when I first came out of school was, I went to Stanford, but I had to reprove myself. I am a smart person, and I had good grades, but I had to reprove myself to the world. And the same thing happened at Goldman. At Goldman, you walk in and you’re immediately at the absolute bottom of the totem pole, and even at Plaid I experienced aspects of that too. I was working there, as a 23-year-old talking to the CPO of a Fintech company and I’m like, “who's to say I can do this?” And so I think over the last couple years I’ve been gaining the confidence that I can do this, I am good at this, I am smart. I think one of the biggest things I’ve realized is, just because I'm young doesn't mean I can't do something and be successful. It has been a big learning experience for me, and a huge reason why I’ve enjoyed my time here at Plaid.
Yeah, that's awesome. And do you have any advice for someone, right out of school, thinking about what their next steps in their career are?
Yeah, I think for me, while I don't regret my time at Goldman at all, I wasn't very creative about what I wanted to do out of school. I really saw it as banking, consulting, tech, and even tech wasn't startup tech, it was Google or Facebook. I think I would encourage someone to have a little bit more creativity in their thought process and encourage them to talk to people across the industry. When I was leaving Goldman, I spent a lot of time talking to PMs, account managers and salespeople to understand how their jobs were different from finance. Once you exit the finance world, there's 1000 things you can do. So I’d say, just spend as much time figuring out what role you really want. That’s something that I never thought about in school at all, so taking the time to really understand what else was out there would have been eye opening.
That’s it for this week everyone. Have a great week!!!!