Unstable Company With Knee Jerk Reactions - Anonymous Calendly Employee Review

1.0
Apr 14, 2025
Recommend
CEO approval
Business outlook

Pros

- fully remote - nice peers

Cons

The culture here has been completely drained. Morale is low, and stress is constant—largely due to the recurring layoffs that seem to happen every three months, triggered by erratic executive decisions. I typically appreciate founder-led companies, as founders often care deeply about their people. Unfortunately, that’s not the case here. The CEO operates with a cold, detached approach, showing little regard for the employees affected by repeated workforce reductions. In the scramble for self-preservation, even direct managers may undermine their own teams to keep their roles—creating a toxic, cutthroat environment where trust is eroded and collaboration is nearly impossible. The culture here has been completely drained. Morale is low, and stress is constant—largely due to the recurring layoffs that seem to happen every three months, triggered by erratic executive decisions. I typically appreciate founder-led companies, as founders often care deeply about their people. Unfortunately, that’s not the case here. The CEO operates with a cold, detached approach, showing little regard for the employees affected by repeated workforce reductions. In the scramble for self-preservation, even direct managers may undermine their own teams to keep their roles—creating a toxic, cutthroat environment where trust is eroded and collaboration is nearly impossible. This company suffers from a lack of strategic consistency. Leadership frequently pivots directions—ramping up hiring and investment around a new initiative, only to reverse course six months later and lay off entire teams. This cycle repeats every few months, making long-term stability nearly impossible. The CEO is deeply involved in every aspect of the business. While understandable given it's his company, this level of involvement often leads to micromanagement in areas outside his expertise. The result is paralysis and confusion rather than progress. The organization can't seem to decide whether it's sales-led or product-led, creating misalignment across teams. People have said for the 3+ years I've been employed, we don't understand the vision. Compounding the issue, high product churn undermines any marketing efforts, making them inefficient and costly. Meanwhile, competitors are gaining ground rapidly. Our lack of early investment in AI—something we’re only now beginning to address—has left us playing catch-up in a space where we could’ve led. On the people side, career growth is virtually nonexistent. Promotions are rare to non-existent, even for top performers. Employees regularly work 60+ hour weeks, earn stellar reviews, and are still passed over without recognition or reward. Promises are made but never fulfilled. Finally, the executive culture is a problem in itself. The COO, in particular, appears more focused on hearing himself speak than on listening, collaborating, or driving meaningful change. Nearly every other executive that has been hired in the last three years has churned, largely I feel due to a culture dominated by ego.

Explore other reviews about Calendly

5.0
May 25, 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
1w
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
4.0
Jun 12, 2026
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

There are a lot of great things about working for Calendly and they've come a long way with improving the culture. Compensation is very competitive, benefits are great, and fun company events and chances to connect with others virtually. Most people that work there are smart and great to work with.

Cons

The company is still trying to determine the best direction with the product. This can lead to uncertainty about future success.

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