Pros
Great healthcare benefits, flexible schedule and ability to work from home (depending on position and department), nice office, and PTO is more generous than some other places. The parental leave policy is also unheard of. These are very real pros that can make Simple a livable and desirable place to work, because these aren’t things that you’ll find at every Portland employer. The product is also genuinely interesting to work on. As a customer, it helped get me out of debt (student loans). Given the right support (depends on what team you’re on), Simple is also a place where you can learn a lot and grow quickly, and I’m so grateful I got that opportunity.
Cons
But the potential and promise of Simple and what it could be is bigger than what it actually is. (This is the part where I’m going to say things that make it obvious to management who I am and I’m aware of that.) Simple says it’s a diverse and equitable employer and has signed a Portland diversity pledge—but what do they really have to show for it? While there are women on the leadership team, they are mostly in areas where you’d expect: marketing, customer relations, and HR (called People Team). Whereas Product and Eng are both headed up by white men. (Finance is headed up by a woman.) Additionally, salary equity is definitely not a thing in many departments. I've heard other stories about women at Simple (across departments) who make less than their male peers. This last fall I discovered I was making $18k less than a male peer. To be clear, we didn’t do exactly the same job, but we were at the same level in the company and could both demonstrably show how our work had benefitted the company. When I found out, I had a new manager (my fifth at Simple, I ended up having six total but that's another story), who was a woman, and she put my name in for an equity review. My salary was increased $15k, but the annual bonus was based on gross pay and also I had been underpaid for more than a year. It sucked to know that this was because my previous manager—a man who ended up leaving the company for undisclosed reasons—had kept me at a lower salary and clearly didn’t see my full value. I am 100% certain that if I’d been with a different manager sooner that this wouldn’t have been an issue. This isn’t new news for a tech company, or any company in general. The bigger problem of all of this is that Simple says that they’re better about this stuff than they are—and when you’re the one underpaid or not getting the right opportunities, it makes you feel like you’re losing your mind. It’s disingenuous. Obviously, this isn’t the case for everyone. I know some folks at Simple who have been paid fairly and genuinely enjoy their jobs and the challenges they get to work on. What I’ve been telling people is: it’s not on-paper a bad place to work. There are a lot of reviews here that suggest it is. I believe those people had poor experiences. I know about some of them because I know some of the reviewers, and their experiences were genuinely awful. And yet, if you need a job with good healthcare and you have the energy and excitement for the product/can deal with the some of the same ol’ same ol’ issues, then this is a place to work (though your mileage may vary by department).