Pros
- Fast moving & growing. Keeping up to speed in the AI era - Personally feeling challenged in a way I haven’t in a long time - “Unlimited” Claude Code usage - Long ramping period (3 months mixed training material, mock chats, buddy sessions, shadowing + 3 months ramping in the inbox) - Hands on experience learning new AI tools - The Support team is incredibly friendly, helpful, and candid in the best ways possible. Can’t really speak for other teams or offices, but pretty satisfied with the culture in Chicago. - Despite being an AI-forward company, they do not try to BS you about the direction that AI is going or force you to use certain tools. Leadership (including execs) are very candid and realistic open about the “AI bubble” and their approach to their current philosophy. It doesn’t feel as “snake oily” as some other AI agent platforms and companies. - Lots of very smart people working here. GTM department actually knows a ton about the product and not just selling out their butts. - Decent office perks - catered breakfast and lunch. Onsite baristas Tuesday morning. Snacks, espresso machine, assorted beverages, etc. - Commuter benefits ($75/paycheck for parking and public transport each) - Free building shuttle that does pick-up/drop-off at Union, Ogilvie, and Morgan CTA stop - Free gym membership in the building. Tons of equipment and not usually super full. Locker room, showers, hair dryers, the works. - Not a huge amount of micromanaging (yet). There are KPIs and SLAs to meet of course but still has a bit of a “start up vibe” despite the company and team sizes.
Cons
- Can be a bit too fast paced for some. Updates and new features are shipped almost daily. If you’re not disciplined at keeping up with the product updates, it could be easy to fall behind. The product is incredibly robust and can be very technical compared to an avg Customer Support role. - Not a lot of hand holding. There’s lots of resources at your fingertips but you definitely have to be proactive with reaching out and asking questions. Might not be a good fit if you’re used to being told exactly what to do. - Can be uncomfortable if you’re unsupportive of AI/LLMs. - Seems like promotions and raises can be slow if you just do the bare minimum. The folks who tend to go above and beyond and are capable of advocating for themselves, volunteering for projects, etc have the most success. - You’re expected to upskill into your new role before actually getting promoted (with no backpay) and sometimes for months. - Not always enough meeting rooms during busy days - Hybrid (3 day in-office requirement) - Company pulled back DEI initiatives so there aren’t a lot of corporate-specific resources. But I was pleasantly surprised how diverse and inclusive many of the teams are, especially Support.