Pros
Toast was the first tech company in Boston to take my nonprofit experience seriously when I was looking to make a switch into direct sales. The team culture is addicting and supportive-- even though sales is competitive, I also felt my peers rooting for me as I got on my feet, switched markets, hit quota.
Management is supportive and fairly transparent across the board. Co-founders will stop to ask your feedback, the CEO recognizes you in the kitchen and checks in. It's clear everyone is excited about our product, what we do to help restaurants thrive, and the company itself. It's a pretty wholesome culture, though there have been plenty of times we played hard to celebrate hard work.
We hire great people, everyone is smart and driven and works really hard. I am especially comfortable selling Toast because I know things will happen for my customers as I say they will, project management is organized and thorough, our support team is EXCELLENT. Thank you guys for letting me sleep at night, and letting my customers sleep too, knowing their POS and the team behind it is reliable.
This is the first time in my career where I'm not worried about the next move for my resume. There's always something new and exciting as the product develops and we partner with more and diverse restaurants. The sales team is growing exponentially and I don't think anyone in the org should feel like they're limited in career growth-- BDR -> reps, inside sales -> outside, outside sales -> inside, SMB sales -> enterprise, outside sales -> management, sales -> sales engineering, etc., etc. Toast rewards hard work and wants to help you achieve career growth; I truly believe and have benefited from this.
OTE is completely realistic and many of the reps that have already ramped will W2 way more. 2017 was the first time we celebrated quota crushers with a Champions Club trip, which is an awesome perk for hustlers and aspirational as quotas evolve as we gain market share.
Sales management is pretty dynamic and open to new ideas. We're hiring reps across the company/country and while it's challenging at times to be a remote employee, RVPs and DMs are touching base frequently and work to create team culture, even if you're not seeing each other face to face all the time.
Cons
Toast is growing in an aggressive way and I think scaling smartly, though there are growing pains and sometimes I think we are too segmented b/t sales, services, account management. We're expected to close close close but also handhold through the project process and are frequently the first number customers dial with questions. Getting better as we hire some awesome managers across the company to help smooth out processes.
