How Expensify Shed Silicon Valley Arrogance to Realize its Gobal Ambitions

How Expensify Shed Silicon Valley Arrogance to Realize its Gobal Ambitions

Expensify may be the most ambitious software company leaving most of the bay as the center of its operations.  Early history is tied to San Francisco representative locations: the founding team worked for months at Pitts Coffee on Mission Street, then collapsed into a penthouse lounge near 4th and King Caltrain stations, then a small office and then a little flat on Market Street.  Thirty years later, there is still an office a few blocks from Expense’s Kearney Street, but it is no longer a San Francisco company or even a Silicon Valley firm.

The company is truly global with employees around the world – and it did so before it cooled the remote work before COVID-19. “Things got even better when we stopped seeing ourselves as a Silicon Valley company. We’re basically saying, no, we’re just a global organization, “CEO David Barrett told TechCrunch. 

That cosmopolitanism has led Michigan to one of the smallest rural towns – opening large offices everywhere. Ironwood’s expansion will eventually lead to a cultural shift that will see the company shift its focus from Portland headquarters in the Gulf region to offices worldwide. It is understood that an organization founded by internet pirates will allow its employees to live anywhere they want and however they want. Yet, how is it able to work perfectly with just one kid to reach $100 million in annual revenue with more than 100 employees?

As I described in the second part of this EC-1, the skills of the staff are partly due to its culture and who hires it. 

This is also because it has attracted top talent from around the world with the option of working remotely all year round as well as providing SF-level salaries to those who are not even on a tech hub basis. It receives a “workcations” for each employee, their partner and children for the full annual pay-as-you-go month. Yet the real story is how an organization can be disciplined from its core geography, willing to adapt to new places and new cultures, and ultimately leave the past as the future unfolds.