Interview with Sima Gandhi, Employee #15 at Plaid

This article is part of a series revealing the stories of early employees from the most successful tech companies of the past few years. You’ll walk away having learned about what these individuals experienced, what they wish they knew, and the advice they’d give to others joining high-growth startups. Key takeaways are at the top and you can find the full interview below. 

‍

This interview is with Sima Gandhi. Sima was employee #15 at Plaid, joining in 2015 and leading Plaid through the Visa acquisition 5 years later. While at Plaid she helped lead company building initiatives – scaling the company from 40 to 500+ – as well as operational initiatives including global business development, policy, and corporate strategy. Below is an edited version of a conversation she had with us here at Compound. 

Note: If you’re looking for an all-in-one solution to manage your personal finances, Compound can help. We can help you diversify concentrated stock positions, optimize company equity, plan asset allocation, and more. Request access here and we’ll be in touch.

Key Takeaways

• On what makes a great manager – “The best leaders I’ve seen put the team’s accomplishments before their own. It’s not what I do, it’s what my team does. I think a lot of leaders (especially in Silicon Valley) have trouble transitioning from, what did I do? to, what did my team do?"
• On the early Plaid culture – “It was a low-ego, outcome-oriented set of values – people just really wanted to build and do awesome things. It was less about the “I” and more about the “we”. There was a lot of space to experiment and fail together in a safe way.”
• On the importance of hiring for diversity – “It’s important to be intentional about preventing homogeneity when you hire. You have to think about diversity and company culture from the very beginning. If your first ten hires all look the same, it’s only going to get harder from there.”
• On why Sima became a founder – “To me, it was really the pull of the product and a desire to build this that got me here. If the product already existed in the world or if someone else could do it better than me, I feel no ego about being here. I just really believe in the problem we’re solving and that  what we are building can help millions of small businesses.”
• On the benefits of being an early employee – “...it’s one of the most fun times to be at a company. There’s no precedent for how things should be done – you are the institutional knowledge. So if you’re an early employee, enjoy the ride and learn as much as you can. You’ll get access to people and leaders that you normally wouldn’t get access to at a big company.”

How did you first find Plaid and what made you interested in working there?

I was interested in working at a place where I could make a bet on myself. At a smaller company, every person’s contribution moves the ball forward. While I loved my time at American Express, there were a lot more layers in order to get something done so you think of things on much longer timelines. I wanted somewhere that had rapid execution.

I had worked in financial services my whole career and wanted to continue building in that space. Plaid was one of the only fintech companies at the time that was actually focused on the tech side of fintech. Back in the day, there were many lending companies, but a lot of them were just better UX on top of an older, brittle technology. Plaid was one of the few focused on the guts of the system. 

What was your original mandate at Plaid?

The engineers at Plaid are phenomenal and they built this amazing technology. But the reality was that the technology was dependent on the bank infrastructure, so we wanted to build better relationships with the banks to help them understand what we were trying to do and mitigate the existential threat to the tech we built. 

My role was to figure out how to build partnerships with institutions that we needed to work closely with in order to build what has become an amazing platform. For a lot of the institutions, there was a big education curve – they didn’t understand what we were doing, or they were skeptical. 

What was unique about the early Plaid team that helped you succeed?

It was a low-ego, outcome-oriented set of values – people just really wanted to build and do awesome things. It was less about the “I” and more about the “we”. There was a lot of space to experiment and fail together in a safe way.

This behavior was modeled by the very early people. It already had that vibe when I got there – it was a really great first core set of engineers. After that, it just replicated itself. 

What are some of the traits that you would love to see out of someone managing a team at a fast-growing startup?

I had been a manager before (so it’s a bit different) but what was unique was the pace of hiring. Our company went from 15 to 500+ in 5 years, and my team alone went from zero to 30 during that same period. It was a lot of hiring, a lot of training. 

The best leaders I’ve seen put the team’s accomplishments before their own. It’s not what I do, it’s what my team does. I think a lot of leaders (especially in Silicon Valley) have trouble transitioning from, “what did I do?” to, “what did my team do?”. 

Or, when the team isn’t meeting expectations, their first instinct is to get into the weeds and do more, but that’s actually counterproductive and demotivating. Instead of coaching or helping to provide leverage, they take over. That might feel productive in the short-term, but it doesn’t work in the long-term. 

How did you find great people to hire?

There’s no better substitute for rolling up your sleeves and tapping people on LinkedIn. I definitely advise looking for folks within a certain degree of connectivity, just because it’s easier when it’s the first couple of hires. 

It’s important to be intentional about preventing homogeneity when you hire. You have to think about diversity and company culture from the very beginning. If your first ten hires all look the same, it’s only going to get harder from there.

Be intentional about vetting for values too. Here at Creative Juice we are still a small team and values are the most important thing. A lot of folks struggle with candidates because they might be really talented, but they can be challenging to work with because they don’t buy into the values. It’s often not worth it. One person who doesn’t share your values can make it harder for everyone else. 

How did you articulate values with employees at Plaid?

We were really intentional about values. About six months after I got to Plaid, we actually did a values exercise to articulate and codify them again. It was always top of mind – they were on our website, everyone on the team could articulate them, and we would talk about them often. You can’t just set values and put them away, you’ve got to make sure you’re living them. If you’re not, they probably aren’t the right values. 

How did you know it was the right time to transition from an early employee to a founder?

When I left Plaid, I didn’t really want to be a founder. That’s not what I wanted to do. But I just really believe what we are building at Creative Juice. There’s a need for a product that helps creators in particular build their business. 

It’s incredibly hard to be a small business owner today and it shouldn’t be. There’s so much tax and regulatory stuff and it’s confusing. To me, it was really the pull of the product and a desire to build this that got me here. If the product already existed in the world or if someone else could do it better than me, I feel no ego about being here. I just really believe in what we are building. 

So my advice would be to find a product and a mission, instead of just a desire to be a founder for the sake of being a founder. That higher motivation will keep you going. 

What advice would you give to an early employee that’s different from advice to a founder?

If you’re an early employee, it’s one of the most fun times to be at a company. There’s no precedent for how thing should be done – you are the institutional knowledge. So if you’re an early employee, enjoy the ride and learn as much as you can. You’ll get access to people and leaders that you normally wouldn’t get access to at a big company. 

At bigger companies (or as your startup gets bigger) you’ll have to specialize and go narrower in terms of your role. So enjoy the breadth that comes with being an early employee because the amount of experience and responsibility that you can get is truly unique. 

I’d also say to use it as an opportunity to build skills that you aren’t going to be able to build elsewhere so rapidly. You’ll get to roll up your sleeves and do things that you’re not qualified to do. Appreciate the opportunity to learn in a hands-on way.