Building a Pro-Employee Company: Updating equity distribution at Expensify

Matt McNamara —  October 5, 2015 — 1 Comment
Jonah and TJ working at Expensify.

Across all teams, we’re building not just a best-in-class product, but also a world-class company.

Part of what makes Expensify such an amazing place to work is that we’ve brought together a group of people that truly believes in the company’s mission and vision. Since 2008, we’ve grown the team from a handful of people to ~100 full time employees while only promoting from within. Every single member of our leadership team has started from the ground level and earned the respect of the organization before being recognized with any formal title; part of our vision is to keep that tradition for as long as we reasonably can.

On top of that, over 75% of our employees have opted to receive some portion of their compensation in stock options. That means over 75% of the team is making a long term investment for ownership in a company they’ve literally helped build along with their hard-working peers.

In short, we’ve created a unique culture wherein employees care deeply about the health and growth of the company, because they recognize that we care about them. With that in mind, I’m very happy to announce two changes to how our stock options plans (ISOs) work to reinforce our gratitude to the people who are building this amazing company and product.

First, effective immediately and retroactively for all ISOs: we’re extending the window to exercise employee options upon separation from Expensify from 30 days (an industry standard) to two years for those that have been with us for three years. Why?

  • The IRS requires a process called “exercising” to convert options into stock. As the value of Expensify continues to rise, this process is becoming more and more expensive for people on our team.
  • There’s a tax burden involved because you’re acquiring a very valuable asset.

After making such a long-term investment working at Expensify, the last thing we want is people worrying about being unable to exercise their options due to the financial burden. We chose two years as the new window because it feels like a good amount of time to save up, but it also doesn’t lock up the options for too long a period of time (preventing us from extending those options to current employees). This added benefit is extended immediately for every employee who hits their three year anniversary, because we WANT employees to exercise the options they’ve worked so hard for.

Second, we recognize that the point of an ISO’s “cliff” is to prevent people new to the team from joining, getting some options, and then bouncing without actually making a significant contribution to the company. But, because we do compensation adjustments every six months and give employees a choice in how many options vs. cash they receive that adjustment in, the majority of employees here start a new vesting schedule every six months. As such, it doesn’t make sense to require that level of protection for the people who have put in multiple years into Expensify.

Therefore, any ISOs that commence after someone’s one-year anniversary will no longer have a cliff. We’ll continue to use the traditional four year vesting schedule with a one year cliff for people in their first year, but subsequent grants will have no cliff and will immediately start vesting over the next four years.

I’ve written on the blog before about using the phrase “family style” to describe how our team interacts with each other. Because of this special dynamic, we are able to truly build a special community across all teams. Today’s announcement is about something different. I’m calling it our “pro-employee” culture. With bi-annual compensation adjustment, quarterly peer review, internal transparency, promoting from within, and now a redesigned stock option plan designed for our employees’ best interest, we’re building a place that people love to work and are treated like the most important assets they are.

Matt McNamara
Former Mid-level Software Engineer
Director of Engineering

Matt McNamara


We're better together.

One response to Building a Pro-Employee Company: Updating equity distribution at Expensify


    Love it when companies go the extra mile to make sure incentives are aligned. Nice work Expensify!

Have something to say? Share your thoughts with us!

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s