Pros
Product org is full of strong leaders and PMs. Solid product and brand. Hire smart people - have cycled through hiring waves from great companies like Drift, ZoomInfo, MongoDB, HubSpot. Similarly, those departures have gone on to work for impressive brands (Anthropic, Intuit, Vanta, Decagon, Ashby, OpenAI, Kickstarter, etc.).
Cons
Thrash, whiplash, pivot, repeat. GTM side of the business is at the mercy of mercurial executive decision-making. Constantly setting unrealistic goals and making big swing experiments to try and hit them. Hired and laid off 2 or 3 entire BDR programs. CEO is high energy, personable, likeable, and hard worker. But unfortunately thinks of himself as smarter and a better seller than any other representative of company (bc it's his baby). Dismissive of any challenge to his big idea/conviction of the week.
There were 3 layoffs of 10+ and several random individual layoffs in my ~1.5 yr there. CEO would casually say things like "well he won't be here next month, lets be honest" or "as soon as we find a replacement she'll be gone".