Horrible leadership, amazing ICs - Customer Success Manager (CSM) Calendly Employee Review

2.0
17 Apr 2024
Recommend
CEO approval
Business outlook

Pros

Super talented ICs and great perks and generous benefits. Loved the perks and the preloaded Divvy card. 401k matching is also excellent. Had the opportunity to work with somebody to biggest brands and super talented co-workers. The CSMs are doing incredible strategic work, despite the poor leadership and lack of meaningful direction/strategy

Cons

What drove me to leave Calendly is how they approach Customer Success. The focus is on how every minute is spent, extreme micromanagement and constant reminders of outstanding tasks, but very little strategic direction. The OKRs/KPIs change constantly, so it’s impossible to succeed on any specific initiative. The whole is very unmotivating and just bad business.

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Calendly Response
2y
Thank you for taking the time to share your feedback about your experience at Calendly. We are committed to creating a supportive work environment that ensures all team members feel valued. Your feedback will be shared with our leadership team.

Explore other reviews about Calendly

5.0
25 May 2026
Recommend
CEO approval
Business outlook

Pros

You have all the resources needed to assist users!

Cons

Calendly is growing fast, which means continuous changes and a fast-paced environment, which will require you to keep up with new information. Since Customer Service provides vital assistance to the users 24/7, the Support team receives less perks!

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Calendly Response
2d
Thank you for taking the time to share your experience at Calendly. It's genuinely great to hear that you felt well-equipped to support our users, having the right resources to deliver excellent customer experiences is something we care deeply about, and it means a lot to know that came through in your day-to-day work. We also hear your note about the pace of change and the experience of the Support team. Feedback like this helps us think about how we continue to invest in the people who are showing up for our users around the clock, and we'll make sure it reaches the right leaders. We're committed to listening, learning, and making Calendly a place where people can do their best work. The Calendly People Team
2.0
20 May 2026
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

Good people to be found, fully remote

Cons

Culture plummeted in my last year or two, and there was never any direction for me or my peers to feel like we had the tools we needed to grow. Priorities were in the wrong place and I no longer felt valued, just simply a number on a roster. My manager also would go from micromanaging to days-long silence, neither of which made for a productive work environment.

1
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Calendly Response
2d
Thanks for being candid about your experience with Calendly. What you've described is feedback we take seriously. The themes you've raised around culture, growth opportunities, and how leadership changes affect the people who've invested in this company will be shared with the appropriate leaders. Everyone who contributes to building Calendly deserves to feel like their work matters. We're committed to listening, learning, and making Calendly a place where people can do their best work. The Calendly People Team
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