As mentioned by many others, success was fairly depended on your territory. If you have a big city with new innovative restaurants popping up all the time, you have it made and will likely be successful at Toast with some good old fashioned hard work. But if you're in a smaller city, there will only be so many "good fit" prospects in the market for you while the performance expectations are the same.
Toast puts a lot of pressure and uses emotional manipulation on its employees to meet their goals. Even if you have a good manager, you will still be treated as though using ANY of your "unlimited" PTO is only an option for you if you are the best of the best in the company. Management will say it's important to take time off and then in the next breath say that they will expect you to work on a company holiday if you have any potential deals that are not closed (even if you're already ahead of your quota). This feels disingenuous and leads to a lack of trust in the leadership.
Burnout is common. A common phrase used internally is "what have you done for me this month." The focus at Toast is always on doing more, no matter what you've done for the company already and this can get tiring if you're with the company for several years as even the top performers on a team year over year are treated as just their latest month's number.
As said by others, managers focus on the aggressive goals without really offering a lot of helpful strategy or executional support to hit the goals. The main feedback given is on pipeline reviews is "how can we charge them more." While the product is valuable, restaurants are hurting now and it feels wrong to only care about getting more money from them when they don't even know if they'll be open next month.
Customers often do not feel that the onboarding and support resources provided are adequate and this means that you will spend quite a bit of time hearing from existing customers about their frustrations with the other departments of the company. Thankfully most peer companies in the space are just as bad or worse, so it's not really a competitive disadvantage in the market, but I like working for a company that provides great experiences, not just average ones.
Toast expects a lot of productivity from sales reps (which is fine) but they haven't put in the work to empower employees with systems and scalable processes to reach those productivity goals. The focus is solely on the outputs and it's up to you to figure out what inputs you need to get you the outputs. This means that many employees struggle to figure it out (if they stick around long enough to do so). Some employees report work related depression or trouble sleeping because they aren't supported but are expected to perform at high levels. If you love high-pressure management tactics then you will be fine.
Much is made internally of specific metrics that can either be fudged (anyone can open more ops just to open ops if they're not really qualified) or don't tell the full story (a food hall could have 10 locations. Some territories have several halls while some have none). I'm happy to celebrate my co-workers success, but at Toast it's sometimes done in a way that makes you feel less effective unless you know the full story, or incentivizes employees to game the system with vanity metrics or sell things in a way that helps your sales numbers even if it's not in the best interest of the customer.
