Help Scout is facing the classic problem of: "what got you here, will not get you to where you want to go." The co-founders have had a decent amount of success over the first 10 years of the business operating in a "peace time" market where money was flowing and poor decision making was covered up with free flowing cash. Since the recent downturn in the market, the CEO's extremely poor decision making has exposed his immature and ego based actions.
The CEO at Help Scout is the epicenter of all of the company's toxicity, accompanied by the yes men/women that are apart of his "circle". The company strategy set by the CEO is based upon the the article, podcast, or tweet that he happened to read that week. In my few years at Help Scout, I've seen the company strategy/vision shift at least 5 or 6 times, with company goals never even being close to achieved. In regards to the CEO's obsession with copying other company's ways of working, this analogy sums up his shortcomings: "Knowing how good kitchens are organized and their dishes is not enough to know what it takes to create them and cook great food."
At the end of the day, the CEO is apart of every decision that happens at the company. He does a great job of creating a facade that people are empowered, but it's really just a mask to create a top-down feature factory. PMs and teams are held accountable for the success of HIS ideas. When HIS ideas fail, all blame is pointed towards the team that executed on HIS ideas.
Shame on the People team at Help Scout, whose job requires them to support both the business, AND protect the people. In reality, they enable the CEO and leadership to create an extremely toxic environment where everyone is in survival mode. If you have a candid conversation with any IC at Help Scout, you'll really get a glimpse into how bad this work environment is.
For any candidate exploring Help Scout as a potential opportunity, I urge you to look past the facade that Help Scout's leadership team will feed you and do some intense due diligence before joining this company. Speak to current and former IC employees, ask questions regarding the work environment, ask about recent turnover, ask about how decisions are made at the company, and ask about how the CEO influences your day to day. I tend to believe there's always hope to turn a ship around, but unfortunately I can't see that happening at Help Scout.
