Pros
-Reputation: Stripe is viewed as a market leader by many potential buyers -Smart people: I rarely encounter incompetence -Challenging work: a pro and a con
Cons
Stripe is clearly an engineer-first organization, and Sales appears to be viewed as a necessary evil. The GTM process is shockingly immature: AE's practically need a PhD to sell. Technical resources are limited. GTM playbooks for users still don't exist for products that are several years old. The biggest complaint is that sales compensation at Stripe is abysmal: -OTE can be competitive for some, but well under market for others. Comp bands vary widely within levels, so coworkers doing the same job could be severely underpaid. -The allure of over-performance is blunted by caps on attainment - reps close huge deals, see a small bump in pay for their efforts, then leave the company because they aren't compensated fairly. Objections are raised during all-hands, and senior leadership always responds the same: "we're on a journey and still figuring out the pieces." It doesn't appear that anyone in sales at Stripe is making >$400k, which is insane for a company of this size. -Revenue is consumption-based, which means reps don't get paid until users start processing volume. The path from deal closure to go-live is often more challenging than getting a signature. This is slowly changing with committed contracts, but those don't exist across all products. -Comp plans are a black box and managers often share MBO's close to the end of the quarter. There are 0 tools for reps to understand attainment at any given time. -Targets are based on expansion goals and not addressable market / real opportunity. Reps are expected to own a book of business w/o clear opportunities. -Employees don't get pay bumps when promoted; they have to wait until annual compensation reviews. Do NOT accept a low OTE joining Stripe in hopes of over-attainment because it's impossible to get a market-adjusting raise once you join. Stripe has a pervasive view that employees need to prove themselves relentlessly before being compensated, vs. paying employees based on the quality of their work. -Most deals require a ton of legal / risk assessment. As you can imagine, this adds an inordinate amount of headache as you interface with people that exclusively exist to tell you how much risk you're generating, with few actionable next steps.
