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      Calendly

      Engaged employer

      Calendly reviews

      CEO hinders strategic direction, decision making, and execution - Product Manager Calendly Employee Review

      3.0
      Feb 7, 2024
      Product manager
      Recommend
      CEO approval
      Business outlook

      Pros

      The IC and management level are awesome. I work across many functions and can't think of one person on the IC/manager level who I don't like working with. Perks and compensation generally on par with other SaaS companies. Although some have been reduced due to budget constraints.

      Cons

      The most challenging and tiresome part of Calendly is the CEO. Calendly's strategic direction is very tops down. Tops down is not a bad thing IMO. It can be clear and efficient. What's wrong with Calendly is: You have product direction and priorities set by the CEO. You have both strategic and tactical decisions (down to copy language and small design choices) being made by the CEO. But then there absolutely no accountability for the CEO. I have heard the CEO complain that Calendly is "not working on the right things." Those things are directly set by the CEO. So if that is true, then that is on the CEO. But there is no accountability for this. There are scope items that are directly mandated by the CEO and then their value is questioned by him weeks to months later. This happens *very, very* frequently. It's fine to question the value, but the teams are put on blast when that item was mandated *by him* (not by the team). It's incredibly frustrating. Velocity of engineering teams is targeted. Velocity is suffering because those engineers don't have approved work because they are waiting on the CEO to approve before moving forward. The cognitive dissonance is frankly astounding. So many issues stem from top down leadership without any accountability built in for the main decision maker: our CEO.

      avatar
      Calendly Response
      2y
      Thank you for taking the time to share your thoughtful feedback about your experience at Calendly. We value your perspective and we are committed to creating a supportive work environment that ensures our team's success. Your feedback will be shared with our leadership team. If you have further thoughts, please do not hesitate to connect with your People Business Partner about your feedback as they are here to support you. We are committed to learning and improving together.

      Explore other reviews about Calendly

      5.0
      May 25, 2026
      Customer service
      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!

      avatar
      Calendly Response
      6d
      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
      May 20, 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.

      2
      avatar
      Calendly Response
      6d
      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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