Pros
-Friendly and supportive people -Positive work culture -Attractive perks -Well-maintained office with a welcoming staff -Attainable goals (though frequently and dramatically changing) -Opportunity to engage in interesting projects if you show initiative -Leading-edge product -Compensation is generally good for the role, despite changes over the years Note: The Chicago office, which primarily consists of sales personnel, has a distinct culture compared to other locations. It is small (around 150 people) and more intimate, with a focus on genuine connections rather than a traditional "salesy" environment.
Cons
-SDR role is now more narrowly focused on high-volume outbound efforts and large campaigns, with less strategic outreach -Limited executive and managerial presence in the Chicago office -Limited career advancement opportunities -Unclear promotion cycles and role availability -IPO seems perpetually imminent -Small office with limited desk space; no assigned desks unless you are in the office five days a week -Varied office cultures across locations -Stripe’s complex ecosystem (with multiple products and use cases) requires significant ramp-up time; staying updated is challenging