Strong benefits and flexibility, but leadership and communication needs improvement - Anonymous employee Fleetio Employee Review

3.0
2 July 2026
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

There are several things this company does well. The benefits are strong, and the remote-first culture is real. The flexibility offered to employees is one of the best aspects of working here. Employees are trusted to manage their schedules and get their work done without unnecessary oversight. The product is genuinely valuable and solves real customer problems. There are talented people throughout the organization who care about the, the product, and doing quality work. The company also provides employees with the tools and resources needed to be successful. Many teams are made up of hardworking people who want to see the organization succeed.

Cons

At times, leadership communication felt inconsistent. There were situations where concerns, frustrations, or challenges were communicated downward rather than being addressed in a way that built trust and alignment. This created uncertainty and impacted morale. Transparency was also a challenge. Information was sometimes shared selectively, leaving teams without the full context needed to understand decisions or changes. This was especially difficult during periods of organizational change. The culture seemed to welcome questions and feedback when things were straightforward, but there was less openness when situations were unclear or when decisions were challenged. A healthy workplace needs room for respectful disagreement, questions, and conversations — especially when the path forward is not obvious. Across teams, it seems that there were competing priorities that took a way from bigger goals for the organization. Another recurring challenge was the expectation for employees to step outside of their defined roles to support other teams or fill gaps. Collaboration is important, but when this becomes a regular expectation without recognition, clear prioritization, or acknowledgment, it can lead to burnout and frustration. These items were often left off of performance evaluations as well.

Explore other reviews about Fleetio

5.0
24 June 2026
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

What’s great about Fleetio is the combination of a strong culture, a product I’m proud of, a market opportunity that feels significant, and coworkers who genuinely want each other to succeed. There is a lot of room to grow, both as a company and as an employee. Expectations are high, but I’ve never felt like I was expected to figure things out alone. In the past, at other companies, I've experienced quite political and internally competitive work environments, and Fleetio could not be further from that.

Cons

The company is growing in a healthy way, which naturally means things change and not every decision is perfect. But its no more change than any other high-growth company. Communication around priorities could be stronger but I have also seen that improve in the last year.

2
5.0
22 June 2026
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

The company is regularly setting and making goals - we achieved and got record bonuses last year. The market has been changing and the company adjusts goals to suit instead of getting stuck. This didn't happen for years and things were starting to struggle with scale. Leadership has shown they're capable of making difficult decisions to correct that. Most unhappy folks I hear is that it's not "the old Fleetio" - which is true. We're a very different company at $100m+ than most folks who were here from $1-10m and don't want any change are experiencing.

Cons

It's a rapid-growth company and going through all of the common growing pains companies at this size does. I'll say they're handling it better than most any other company I've been at that has gone through this.

2
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