How This CEO Applies a First-Principles Approach to Remote Leadership

Janey Zitomer
July 31, 2020

Most people are notorious for throwing out manuals or shoving them in a drawer, never to see the light of day. But Flatfile CEO David Boskovic isn’t most people. 

When he was a teenager, he taught himself to code by reading the 600-page manual for PHP and SQL, and his initial curiosity in software led him to build multiple B2B SaaS companies over the course of a decade. That same passion, coupled with an interest in a first-principles approach to leadership, brought him to co-found Flatfile, a data onboarding platform. 

The CEO said he often compares the idea of first principles to being stranded on an island and having to build an engine without any background or experience. 

In such a situation, most people would try their best to remember everything they knew about engines. But Boskovic recommends working from a basic understanding of heat, gas and energy instead. 

“It will get you where you want to be much faster –– that is, as long as you have the appropriate materials at hand,” he said. 

The outlook isn’t dissimilar to how he himself became a business leader. 

“You can’t just copy success,” Boskovic said. “You need to understand its building blocks.”



Tell me a little bit about your background. What sparked your interest in the world of data?

My dad had a small business and in my early teens, I wanted to learn web development. And so I asked him if I could build his business a website. I spent two years building a perfect e-commerce platform from scratch, generally before e-commerce platforms existed. I learned everything about databases and programming. And I just fell in love with it. The moment I started writing code, I couldn’t stop. 

By the time I was 15, I knew how to code pretty much anything. I’d read the 600-page manual for PHP and SQL. I also learned a lot about running and working in a business from my parents. That gave me early insight into what it would take to run my own company.

The moment I started writing code, I couldn’t stop.’’ 

In your words, what’s Flatfile’s mission? What problem are you solving for your users?

I think every good business evolves from a personally-felt pain. In my experience working for and building SaaS companies over the last 15 years, the pain of getting a customer’s data into a product is incredibly high. Most software companies are empty box products. You build a box and the customer puts their data in it. And then the box does something magical. Take a CRM, for example. Users need to be able to upload years of customer relationships before they can run a marketing campaign.

We take care of getting the data from whatever format the user has it in into our customer’s products in a clean way. In short, our mission is to remove barriers between humans and data.


You lead with a first-principles approach. Why? And what has doing so taught you?

Leading with a first-principles approach allows leaders to understand problems that they weren’t necessarily trained to solve. You might not have been trained to lead a team of 100 customer success managers, but if you care deeply about our customers and demonstrate empathy for your team, you’ll be much better set to scale with the company. 

Most people reason by analogy. We try to use strategies that have worked before rather than understanding how to make systems or processes work in the first place. And so the core business advantage of taking first-principles thinking is that everybody generally gets to take on challenges that allow a business to grow quickly. And people can keep pace. 

Especially at an early-stage company, the organization grows a lot faster than people grow. And that means that the people who are really good at their job today are actually going to be pretty bad at it tomorrow. How do you solve for that? Do you just constantly go through people? Or do you have a system in place where people can actually scale with the business? 

Especially with a whole team of people all tackling new problems, you won’t always get perfect experience outcomes. Instead, you want people to think through problems in a way that allows them to understand why they’re making decisions.


If you could have one professional do-over, what would it be?

Boskovic offers advice that has helped him lead Flatfile: “Don’t try to copy others.” When facing problems, understand what problems matter most and solve for those. Otherwise, you might lose sight of the problem itself. “It’s taken years for me to actually understand the core problems behind a new challenge.”


Tell me about your approach to remote team leadership. How do you build a culture around a remote workforce?

The hard truth is that not every company is designed to be remote. Fortunately, generally the more technically-oriented the problem a business is solving, the more it lends itself to a remote culture. 

In the interview process, we often try to build an understanding of what someone is used to outside of work. If they say, “I love hanging out with my co-workers,” or “At my last job, we did all this fun stuff as an office,” and there’s not a rich personal life there, that person is almost definitely going to burn out at a remote job. 

When it comes to remote office culture, don’t force it. One of the key elements of remote culture is individual independence. I think a lot of remote companies simply try to make a remote version of what they’ve seen in an office before. Very few people genuinely enjoy getting on Zoom and drinking. We try to find things that are unique to remote. For example, we created a competitive customer trivia game that everybody can play asynchronously.



What traits do you look for in candidates? And what positions are you looking to fill this quarter?

We look for people who have historically demonstrated the ability to be what we call “informed captains” –– people who are able to own an area of the business and practice good judgment. We want employees who can take risks and lead decisions forward without having to look to someone in a senior role for direction. That idea ties in with first principles. Can this person tackle a problem they haven’t seen before and make a good decision, purely because that challenge is within their scope of ownership? 

We’re currently hiring across the board. We’re hiring for engineering roles, design roles and go-to-market roles in sales and marketing content. We also have open ops roles like head of compliance and customer support.

Jobs at Flatfile Inc.2 open jobs
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Design + UX
Dev + Engineer
Flatfile Inc.
Design + UX
Flatfile Inc.

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