Pros
Technically complex product - in addition to web and mobile surfaces for both consumers and merchants (and the data and infra to support them), there's an entire team working on compiled desktop software Strong culture -- really like their 4 core values of Shared Humility, Authentic Relationships, Warrior Spirit, and Joy Every Day Lots of learning (and helping) different types of small businesses, from coffee shops to restaurants to gyms, bars, and many different verticals. Great place to learn about a bunch of different industries (if you seek it out) Unified leadership team that makes time for people and tries to listen
Cons
Challenging pace -- SMB is a tough segment to crack, and that's FiveStars' core merchant demographic. It impacts the intensity of work from sales to account management and support to engineering and product Lots of focus on small business / local business / brick and mortar, so that's a con if that's not interesting to you