I've been with a Hospitality SaaS startup (~30 employees, 10 AEs) for the past 3 months as an AE. They've left me to my own devices and are generally very hands off. This is great because I don't like being micromanaged, but it's bad in that I have very little support from the rest of the team. In these first three months, I have closed as many deals as the rest of the sales team combined. The territory is massive - I'm the lone rep in the largest city in Canada. The product is promising, but if I'm completely honest it's not ready for market. I've spent most of my week addressing bugs during an onboarding instead of selling, which is a big problem.
Recently, a more established player in the field approached me about an opportunity with their company. The company is publicly traded and well established in the retail SaaS sector and is making a push into hospitality SaaS. I would be one of 5 field reps in the same metropolitan area. They have dedicated teams for onboarding, customer success, and several other things which I currently do at the startup.
The second company is putting me through multiple rounds of interviews and moving very fast, I expect an offer from them soon. Same title, same base, slightly lower OTE, same equity package (in today's $ value, but a fraction of the Series A if they make it).
My question is this - all things considered, would you stay with the Series A for the high risk/reward potential of having equity at this early stage, or join a more established player in a market facing heavy competition from several new entries in the market?
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