Headway
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0
Top 20% of Companies
Headway
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Current Employee Nobody really gets into sales for the work-life balance, but at Headway it’s particularly rough. The role is marketed as an Account Executive position, but once you’re in, it becomes clear that it doesn’t align with standard AE responsibilities or compensation. That bait-and-switch is frustrating, especially when you know what AEs at other companies are making.
Attrition is high. You can be at the top one month and on a performance plan the next. Even if you’re contributing in multiple ways, two bad months can put your job at risk. The pressure is intense and doesn’t let up.
That said, the best part of the job is the customer base. If you’re working with therapists, the conversations are generally positive and the product is free for them, so outreach feels meaningful and well-received.
I wouldn’t recommend this role unless you absolutely have to — but if you’re in a tough spot or just starting out, it can be a stepping stone.
3.3
Aug 5, 2025
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