Calendly

• Great perks
• Well-known product
• Ability to work on challenging problems
• Tope's story of starting Calendly is inspirational

• Promotion is painfully slow, with the process changing every two years—often for the worse.
• Employees were once told that failing to get promoted within two years means they are underperforming.
• Nearly all engineering leaders who built Calendly’s foundation have recently left.
• New engineering leadership appears out of their depth and is quietly replacing existing talent with their own hires.
• The company rewards loud voices, not real contributors.
• Consistent actions damage morale, including layoffs, public blame-shifting, and dismissive comments.
• Leadership announced an expensive new SF office during layoffs—then expressed “disappointment” at the employee backlash.
• Leadership repeatedly greenlights projects only to block their deployment, pivoting at the last minute. Let your teams do their jobs.

The reason everyone is leaving is simple — you killed the culture. We used to “start with human,” genuinely caring about employees and customers. Now it’s “start with leadership and shareholders.”

Announcing mass layoffs a week before the holidays? That didn’t win you any points. But worse, you blindsided people. Employees with recent promotions, awards, and glowing feedback were cut. Why would anyone stay when going above and beyond means nothing?

Look at the Trust and Safety Team — gutted. They won the Better Together award twice, a record no other squad matched. Their manager, voted best of the quarter, was let go. Squad members drove developer growth through Tech Talks, demos, and Stability and Response guild participation. Every single person laid off had won an innovation expo award in each of the last three cycles, and helped guide building all three. One of those projects saved the company a million dollars a year in SMS costs. They pioneered a working on-call rotation, supporting two micro-services and spam mitigation, even mentoring other squads. They even tackled abusers, attackers, and compliance concerns after hours without being asked. That’s the kind of dedication you discarded.

You used to lead with empathy. When times were tough, you showed us the numbers, collaborated on solutions, and earned our trust. Now? Employees feel like numbers. And the ones you let go were some of the best among us.