Reviews by job title

5 reviews
5.0
11 Jun 2020
Recommend
CEO approval
Business outlook

Pros

Very much enjoy working here. Some recent, negative review are not taking into account two things: 1) this is a small but rapidly growing company. I mean RAPIDLY...so the pace can be a little frantic at times. That's the excitement of working for a company that is growing in spite of the things going on in the world. The hard work we're doing now will reward us later on. 2) the CEO is the boss. If you do what he asks you to do, you'll be fine. If you feel the need to butt heads with him, you'll be sorry. You can't have it both ways. Every co-worker is awesome, we get a lot of autonomy as long as we show we're getting the work done. As a fully remote company, you get a lot of autonomy...so don't abuse it. When we were all traveling freely we used to meet quarterly...a great opportunity to share a meal with your co-workers and celebrate successes. These days, we try to do events "remotely" to keep up morale and encourage bonding. It's all good.

Cons

Again, the pace is fast, expectations are high and the boss is charging hard to put out a great product. You have to keep your head down and your shoulders broad. It can be a challenge sometimes to get advice/direction from the CEO, because he's pulled in several directions at once. You have to be a fast learner, and be willing to ask those around you for guidance.

1.0
30 Jul 2025

Management pays employees for 5-star reviews - horrible place to work

Anonymous employee
Recommend
CEO approval
Business outlook

Pros

Decent product, cobbled together from multiple acquisitions. Remote work Decent pay for some roles

Cons

**Toxic culture, authoritarian leadership — avoid at all costs** Working at Files.com was one of the most demoralizing professional experiences I’ve ever had. The company is run by a CEO with an obsessive need for control and zero understanding of effective leadership or people management. Every Slack message is monitored, all emails are read, every call is recorded — even the most minor slip-up can trigger public humiliation on company-wide calls. The CEO is a copy of Anthony Fremont from It's a Good Life (The Twilight Zone). He never held a real job, knows nothing of how to manage people, and is absolutely in everything that happens. There is no room for honest feedback, collaboration, or cross-functional teamwork. You're discouraged — even punished — for contacting colleagues in other departments directly. The CEO reacts with extreme hostility to any perceived mistake. Teams are regularly fired in full for a single employee’s error. Examples include: - The entire Sales Engineering team was terminated over one technical response. - The entire SDR team let go because one person over-emailed a prospect. - Customer Success was wiped out because one employee wrote a lengthy message. Policies are dictated through a massive internal handbook written by chatGPT — he added over 90 pages long in a matter of days, filled with vague, contradictory, and often bizarre directives. One section even encourages employees to report (“Name Names”) on colleagues who simply express dissatisfaction or raise concerns. The executive team exists not to lead, but to enforce the CEO’s views without question. There’s no ownership, no accountability, and no room for professional judgment. Management’s main function is to report perceived employee failings directly to the CEO for retaliation. Employee turnover exceeds 50% annually. Unsurprisingly, the company failed to secure its last funding round. Morale is non-existent. Fear and silence are the default state. Sales are tanking with the weakest sales leadership and methods I have ever experienced. If you're considering a job here, ask yourself: - Are you okay with being under constant surveillance? - Can you work in an environment where mistakes — even perceived ones result in public shaming or mass firings? - Do you want to work somewhere where speaking to another department could cost you your job? Bottom line: This is a hostile, unstable, and psychologically unsafe workplace. Proceed with extreme caution.

2.0
14 Feb 2018

Lord of the Flies

Anonymous employee
Recommend
CEO approval
Business outlook

Pros

You'll get to work with some great people. The company is cash-flow positive and makes money.

Cons

Company touts itself as "Holocracy Powered" but don't be fooled, it's absolutely run by the owner as his own personal fiefdom. Three out of around twenty people fired, without prior warning in a years time is a significant percentage of the company. That's bound to have an effect on morale.

1.0
3 Apr 2026
Recommend
CEO approval
Business outlook

Pros

They used to give catered breakfast.

Cons

This company suffers from deeply problematic leadership and a chronically unhealthy culture. The environment feels unstable, isolating, and driven more by the CEO’s whims than by any clear, long‑term vision. Senior leadership is heavily centralized around the CEO, who appears more self‑focused than future‑focused, with little evidence of a coherent strategic vision or meaningful goals for the organization. Decisions are frequently made “because the CEO said so,” creating a culture of fear and compliance rather than collaboration or healthy debate. Leaders rarely show the courage to challenge questionable decisions, which erodes trust and discourages honest feedback at every level. The interpersonal environment is often demoralizing, with employees being berated or put down in ways that drag down morale and make the workplace feel, at times, hostile rather than supportive. Instead of elevating people, the tone from the top tends to bring teams down, validating many of the concerns raised in other negative reviews. Over time, this behavior creates an atmosphere where employees expect criticism instead of coaching and are more focused on avoiding the spotlight than doing their best work. Communication and transparency are also serious weaknesses, especially between remote and in‑office staff and across different teams. Remote and in‑person employees are largely siloed, with little understanding of what is happening elsewhere in the company, which leads to confusion and a lack of cohesion. Entire teams or individual employees are sometimes let go without clear, timely communication, leaving others to discover major changes months later and further undermining any sense of stability.

2.0
31 May 2026

Strong Platform, Great Benefits, and a Missed Opportunity to Retain Employees

Anonymous employee
Recommend
CEO approval
Business outlook

Pros

One of the biggest advantages of working here is the company’s commitment to maintaining and continuously improving its platform. The engineering team is highly responsive, consistently enhancing functionality, introducing new features, and resolving issues quickly to ensure a smooth experience for both employees and customers. The company also offers comprehensive benefits and decent PTO.

Cons

The biggest challenge I experienced was a lack of effective management and leadership support. Managers often appeared to have little authority to advocate for their teams or influence decisions that directly affected employees. It was common to hear that concerns were understood and even agreed with, but that nothing could be done because decisions had already been made at higher levels. Over time, this created an environment where employees felt unsupported and disconnected from the decision-making process. Leadership communication and organizational priorities often seemed to be driven by the preferences and mood of a single influential individual, whose presence extended across nearly every required communication channel. This made the work environment feel unpredictable and contributed to low morale. Ultimately, I chose to leave because I felt I lacked the guidance, advocacy, and leadership support needed to be successful and continue growing within the organization.

Viewing 1 - 3 of 5 Reviews

Glassdoor has 92 Files.com reviews submitted anonymously by Files.com employees. Read employee reviews and ratings on Glassdoor to decide if Files.com is right for you.