Pros
In my many years of senior leadership scaling startups I've never seen a place with so much potential (screw it up so badly). They had a growing culture of passionate, smart, collaborative people across a bunch of different departments with the capacity and talent to deliver greatness. They had a core product that cyclists loved even with all it's bugs, problems and slow delivery -and they had the opportunity to make it exceptional.
Cons
Executive leadership was in way over their heads and, instead of leveraging all the incredibly experienced talent they hired to help them create clarity, focus and a clearly defined strategy and plan, they micro-managed and wanted to do everything all the time and change it practically daily, burning out the people (including the senior leaders!) in their efforts to feel effective. Everything was driven by the whims of the CEO, who clearly demonstrated he knew a lot about cycling and absolutely nothing about running or growing a successful startup company beyond duping investors into constantly giving them more money to burn on useless consultants and grandiose plans. I've never spent so much time "managing up" in my entire career and being mortified by the exec team's complete inability to work together to align on a clear and adaptable strategy so the talented people on the teams could execute successfully. Product development became more of a slogging process to placate the board and c-suite than to allow actual product development leaders to do their jobs effectively and deliver iterative value to the business and customers. Three layoffs in about 3 years, the last one torpedoing about a third of the company, with additional "quiet" layoffs continuing to happen, clearly signals this company (and in particular the CEO) never learns from their mistakes. No matter what they offer you in terms of comp or title it won't be worth sacrificing your integrity to work for the exec leadership at Zwift.
