I looked at the polls[1] and specifically at the demographic of small bushiness owners, which I assume are most of Expensify's customers, and it seems he's talking to a 'lean trump' or toss up audience. How would Expensify's board justify the CEO making this kind of political speech using company channels when it's likely a half to a third of their customers are going to respond poorly?
https://www.uschamber.com/press-release/small-business-owner...
https://www.fundera.com/blog/election-2020-survey