Does Expensify Represent the Future of Culture?

A few months back, I was asked to make a list of CEOs that I think represent the best of purpose-driven leadership. One of the names I wrote down was relatively unknown at the time: Dave Barrett, Founder & CEO of Expensify. This week, Expensify went public. A day later, Dave sent the most extraordinary email to his customers about their journey. I’m more convinced than ever that his incredibly unique style of leadership is something everyone can learn from.

Let’s rewind however to October 2020 – twelve days before the election. That is when I received the first email from Dave. It was titled, “Protect Democracy, Vote for Biden.” It went to every single user of Expensify, all 10 million of us. In it he stated, “As CEO of this business, it’s my job to plot a course through any storm—and all evidence suggests that another 4 (or as Trump has hinted—8, or more?) years of Trump leadership will damage our democracy to such an extent, I’m obligated on behalf of shareholders to take any action I can to avoid it. I am confident our democracy (and Expensify) can survive a Biden presidency. I can’t say the same about Trump. It’s truly as simple as that.” 

To say it was explosive is an understatement. He was accused of violating customer’s corporate lobbying policies, misusing customer email addresses, and he received death threats. While I agree with the vast majority of his concerns (and this was before the aftermath of the election), I still can’t believe he sent it. But that’s when I learned more about how Expensify functions as a culture and a business.

First, he conferred with employees before sending it. He floated the idea to everyone on Slack. Then invited all employees to edit the letter. He asked them to vote on whether to send it and required a super majority to do it. That is how Expensify makes a lot of decisions — democratically. They vote on everything from new ideas to how people are compensated. They have no managers or titles, letting leaders emerge based on the quality of their contributions.

Second, he believed sending the letter was the right thing to do, and not likely to hurt the business badly. He was right. Not only did he post the highest quarterly earnings in the history of the company afterwards, but applications to work at Expensify tripled. Cancellations were few. “Customers want to work with brands that share their values, and I think that the value of promoting democracy is a pretty universal one,” said Barrett at the time.

The next Dave email came in January of this year asking us to vote on how Expensify should donate $3M to organizations focused on climate, housing, reentry, youth and hunger — and encouraging organizations to apply for up to $100K grants. How did they arrive at the $3M number? It was by looking at the largest pay gap between white men and other gender/races (.25 cents on the dollar) and making a donation for every dollar paid to white men in the company to their foundation. His note was one of the most transparent and raw explanations of how an organization struggles with the reality of bias internally, but also the decision to try and do something to help.

This week’s email highlighted his origin story of wanting to give homeless people a card to use for food. An accomplished engineer with a successful exit behind him, he built the entire system but no one would partner with or fund him. It was only when he switched the idea to a card to do expenses was he able to build a successful business. But he never lost sight of the desire for impact, with “Save the World” being one of the company’s three core values. He now offers a product similar to the original idea.

Expensify would not have succeeded without a great product solving a big pain point. However,  I think they also represent some of the most interesting ideas emerging in culture. The democratization of idea generation and leadership. Radical transparency, inclusivity and flexibility. The value of direct communication with customers. The willingness to be courageous. Last, but certainly not least, that every company has an opportunity to help save the world. You just have to find the best way for you to make that happen.

Quote of the Week:

“Only those who will risk going too far can possibly find out how far one can go.”  – T.S. Eliot

Are you ready to build a better working world?