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