Pros
The product has a lot going for it, and it's easy to understand why Connecteam has grown as quickly as it has. The platform solves real problems for frontline workforces, and many customers genuinely love it.
The people were easily my favorite part of the job. The U.S. Customer Success team built a strong community and culture despite the challenges we faced. We regularly shared ideas, supported one another, and celebrated wins without being asked to. The amount of support I received from teammates after I was let go says everything about the people I had the privilege of working with.
Working with enterprise customers also gave me opportunities to build scalable processes, AI workflows, and documentation that I'm genuinely proud of.
Cons
This role is best suited for someone who enjoys working independently with minimal direction. Resources, documentation, and processes often lag behind business needs, so you'll need to be comfortable figuring things out on your own.
The product has been incredibly successful, but leadership has openly shared that Enterprise is not currently the company's primary target market. As a result, customers with 500+ users can encounter product limitations and bugs that make it difficult to consistently deliver the white glove experience expected of an Enterprise CSM.
Onboarding can also be lengthy. While the goal is roughly three months, mine lasted closer to six because of staffing shortages on the onboarding team. I learned the product extremely well, but I often felt the enablement program focused much more on product knowledge than on developing Customer Success skills such as account strategy, executive communication, or managing complex enterprise relationships.
One consistent frustration was the lack of coaching. Feedback often centered on what wasn't going well, while wins, best practices, and peer learning were largely driven by the team itself instead of leadership. Many of us wanted more examples of what great looked like rather than simply hearing where we fell short.
Communication between leadership and frontline teams also remained a challenge throughout my time there. Many teammates across Mid Market, Enterprise, and Strategic felt leadership was disconnected from the realities of managing large customer portfolios. Feedback was frequently requested, but many employees felt uncomfortable being candid because there was a perception that speaking up carried risk. Whether that perception was accurate or not, it affected morale.
Customer Success also felt highly siloed. Teams often developed their own solutions without much collaboration across the broader organization, making it harder to scale successful ideas.
As a U.S. employee, I also felt there was a disconnect between the Israeli leadership team and the day to day experience of the American Customer Success organization. Many U.S. employees expressed a desire for stronger American representation in leadership because they felt regional challenges weren't always fully understood.
The biggest operational challenge was workload. Enterprise CSMs were expected to proactively manage books of roughly 60 accounts while delivering a high touch customer experience. Between extended onboarding times, hiring delays, and understaffing, many of us simply didn't have the bandwidth to provide the level of strategic partnership customers expected.
Leadership communicated that 2026 would be focused on driving efficiency, which was encouraging. However, many of the process improvements and staffing investments needed to support that vision never seemed to materialize quickly enough, leaving teams to work around broken internal processes instead of fixing them.
Compensation also appears to be below market compared to similar Enterprise Customer Success roles. After entering the job market again, I realized my base salary was roughly 10% below comparable positions, and unlike many SaaS companies, Connecteam does not offer an OTE structure for Customer Success.
