[aka1234]

Not to be glib, the difference between $1k on the check and $1k expensed doesn't make a difference if you're well paid. If you're considering how it'd impact your tax bracket, it doesn't matter to you.

But for the customer support reps? It might make all the difference in the world. Most of those employees won't have an extra $1k laying around that they can forego until finance gets around to finally reimbursing them for their expenses. For the average customer service rep, the question will likely boil down to:

1.) Can I not pay a bill (or three) right now so I can take advantage of the program?; or 2.) Do I not participate in the program.

A couple years ago I had similar dilemma with expensing around ~$400 for something. At the time I made about $50k/year and was supporting two households in two separate cities. It took a lot of juggling household budget(s) to wait for the 4 weeks it took to get that money back. That was a lot of added stress when I was already working paycheck-to-paycheck.

Today? I make over double that. If I had to put out $1k, I could do so without blinking. But I live a VERY different life now than even 2 years ago.

[xyzzyz]

It makes large difference if you're well paid. You can only buy ~$650 worth of stuff from $1k in paycheck, but you can expense full $1k of stuff in the other scenario. Of course, you could argue that if you're well paid, you can spend additional $500 of your own gross pay to top up that $650 to full $1k, but clearly Shopify doesn't think this way, because if it did, it wouldn't give any extra $1k in the first place, and just tell their employees to get what they need and pay for it themselves.

[gamblor956]

Tax guy. I second this comment. It makes a huge difference for the non programmers how this is done from both an employee cash flow and tax perspective.

At my previous job, I was asked to go to an international networking event in Europe. The firm would have reimbursed my expenses. I was prepared to go until I discovered that the trip would cost $22,000. The firm wasn't quick enough with reimbursements for me to justify paying for it upfront, so I had to pass.