scorecardHow to get a job at Expensify, the software company that just went public and made 40% of employees on-paper millionaires
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How to get a job at Expensify, the software company that just went public and made 40% of employees on-paper millionaires

Rachel DuRose   

How to get a job at Expensify, the software company that just went public and made 40% of employees on-paper millionaires
Careers4 min read

  • Expensify's November 10th IPO made many of the 140 employees millionaires on paper.
  • The software company has a flat organization structure — meaning employees manage themselves.
  • Expensify employee Adele Kennedy told Insider how candidates can navigate the rigorous hiring process.

As dream jobs go, Adele Kennedy couldn't be happier to hold a title she barely knew existed before finding the listing two years ago.

"It was one of the best things that's ever happened to me," Kennedy said.

It was January 2020, and Kennedy had been feeling jaded in the recruiting space. Then she found a posting for "people operations generalist" at the expense management software company Expensify. The opening felt like the perfect opportunity to continue her talent acquisition career while growing in other fields.

Today, Kennedy is a proud member of the 140-person team at Expensify, which recently went public on Nov. 10. As Insider previously reported, the IPO made 50 of the company's 140 employees on-paper millionaires — with fully vested options worth $1 million or more at the IPO sale price of $27 a share.

In addition to the company's growth, Kennedy pointed to the attractive benefits as appeals for job seekers.

For instance, every employee is paid a competitive "San Francisco salary" no matter where they work, Kennedy said. This is in addition to the medical leave, parental leave (for those who are birthing, non-birthing, adopting, or fostering), mental health leave, and unlimited PTO.

Expensify is perhaps most unique, however, in that everyone is considered a generalist — free to dabble in any area of the business they want, provided they have the interest and time to pursue it.

"The autonomy you have to work on the things you care about is huge," Kennedy told Insider. "It's a lot of personal responsibility because I structure my own day. I pick up the things that I want to work on, whether it's this interview, or it's writing a design doc, or it's getting into coding."

Expensify has open positions for job seekers at every stage of their career — from student ambassador to intern to engineer. Kennedy walked Insider through the hiring process and shared how interested candidates can stand out.

A unique (and lengthy) hiring process

Expensify's hiring process has 12 steps, and candidates can be cut at any point in the process. Interestingly, they can also pause the process and return to it months, or even years, later.

To start, rather than requiring a résumé, Expensify asks candidates four questions when they apply: Do you have a website? What's your coding history? What do you want to do with your life? And how can Expensify help you do that? and How did you hear about us?

"We think that a great engineer can come from anywhere," Kennedy said. "We have hired lots of people with non-traditional experience, like self-taught engineers."

The candidate will then go through a phone screening, receive an un-timed take-home challenge, and be paired with an engineer who can answer questions and will review their final product.

If the candidate passes the take-home challenge, they will meet with an engineer for a second phone call. This call will take at least 45 minutes and is meant to give candidates time to ask questions about the company's structure.

The final stage is the day-long "onsite" — a seven- to eight-hour interview (which now takes place virtually due to the pandemic).

Over the course of the day, candidates will complete two, one-hour challenges. The rubric for grading these challenges will be shared with the interviewee before they begin the challenges. An engineer will be in the room for the entirety of the challenge to help the candidate if they get stuck.

However, candidates are also encouraged to use Google, Stack Overflow, and pieces of old code, Kennedy said.

"We're not asking them to solve a problem in a vacuum," she said. "We want them to build something with as many resources as they need to do it like you would in real life."

At the end of each challenge, the candidate will present their final results, answer questions from employees, have one-on-one chats about company culture, and ask employees any questions they have in a Q&A.

The day ends with a logic problem and a one-on-one conversation with the Expensify CEO, David Barrett.

Expensify's hiring process is challenging, but Kennedy said she thinks it has allowed Expensify to find the perfect employees for the company.

"This isn't for everybody, but the people who it's for, have been here for eight-plus years," Kennedy said, adding that half the company has been there for over four years. "We're way above the average retention rate of two years for Silicon Valley people."

Checking three (but really two) boxes

Throughout Expensify's "exhaustive" hiring process, as Kennedy dubs it, the company is looking for three qualities: talent, ambition, and humility.

Expensify gauges talent based on how job candidates can succeed at their challenges using the tools at their disposal — without the hand-holding of another engineer.

"Talent is focused on basically what you can learn without being directly taught," Kennedy said. "So it is hugely important that they come in with this sort of innate ability that you can develop over time to pick things up."

Ambition is shown through a candidate's application responses and conversations. Given its flat organization structure, Expensify needs employees who are self-motivated to achieve.

Lastly, humility is based on a candidate's ability to come to an agreement with current employees to solve their challenges, Kennedy said. "Humility isn't saying, 'you have the better solution than I do.' Humility is saying, 'This is my idea, but I also respect your values and your opinions. Let's work towards the best solution we can come up with together.'"

Even with all that said, Kennedy told us Expensify's philosophy really boils down to a simple mantra.

"We only have two rules here," she said. "Which is get shit done, and don't ruin it for everybody else."