Product Manager

📍 Location: Remote (USA or Canada-based)
💼 Type: Full-time
💰 Compensation: $110,000 - $250,000 (subject to qualifications and experience) + equity + premium benefits

At Files.com, Product Management isn’t “write the PRD, update the roadmap, call it a day.” This is a Builder’s PM role in an engineering-first company—someone who can see the destination clearly, then drive the work all the way across the finish line. That means taking messy customer reality and turning it into shipped product that’s coherent, durable, and measurably better for the people who rely on us.


Files.com powers mission-critical file transfer and automation for 4,000+ brands. Our customers aren’t browsing—they’re operating. They need workflows that are safe, auditable, permissioned, and predictable under pressure. The Product Manager owns outcomes in that world: fewer sharp edges, clearer workflows, safer operations, faster onboarding, and capabilities that scale with enterprise complexity.


This role demands real product taste and real execution. The best PMs here know what matters, what’s noise, what’s worth building, and what should be simplified—or deleted. They make tradeoffs explicit, keep teams focused on outcomes over output, and execute. Because at Files.com, decisions aren’t real until they ship.


Writing matters. A lot. Product Managers at Files.com write documentation customers and teammates truly depend on—clear, structured, accurate, and actionable. Docs aren’t an afterthought. In enterprise software, confusion is a bug, and great documentation is part of the product.


Finally, this role demands deep domain mastery. We compete in a crowded, sophisticated market. Winning means understanding customer workflows and competitor products well enough to differentiate on purpose—not by copying features, but by building with conviction. The PM becomes a true expert in the space, often understanding competing patterns and tradeoffs more clearly than the vendors selling them.

Who We Are

We’re Files.com, a profitable, founder-led SaaS company powering secure file transfer and automation for 4,000+ brands you know: Marc Jacobs, GrubHub, Michelin, Hot Topic, Stamps.com, Planet Fitness, KFC, and more.

Our CEO is an engineer and remains deeply involved in the engineering team. Files.com has built a $35M+ business with just 70 people by hiring smart, high-output teammates who own outcomes and raise the bar. Backed by $46.5M from Riverwood Capital, we’re scaling intentionally — and Infrastructure is at the heart of that growth.

What Makes This Role Different

⚡ A Builder’s PM in an Engineering-First Company

You’ll work with builders who care about quality, reliability, and long-term maintainability—and you’ll be expected to match that bar. When the customer problem is real and the thinking is sharp, teams move fast.

🎯 Product Taste + Execution (Strategy is only real when it ships)

This is not roadmap theater. You’ll be empowered to cut scope, remove junk, simplify workflows, and drive outcomes without waiting for permission.

🏢 Enterprise Reality, Not Toy Problems

The work is “real”: permissions, audit logs, policy controls, identity, reliability, safety, integrations, and operations. If you like gritty, high-stakes product problems where details matter, this is the arena.

🧠 Differentiation Through Domain Mastery

You’ll learn the space deeply—customer workflows and competitor products—so Files.com can choose battles wisely and differentiate intentionally with conviction and clarity.

✍️ Clarity Through Writing (Docs are part of the product)

You’ll write specs, decision logs, customer-facing docs, release notes, and internal guides that people actually rely on. Clear docs reduce ambiguity, accelerate engineering, and make enterprise users successful.

🔒 Security and Trust Are Core (and PMs shape it)

Trust is the product. Security isn’t a checkbox bolted on at the end—it’s part of the user experience: safe defaults, clear permissions, auditability, and low-risk operations.

🚀 Speed with Rigor

We ship continuously, but not recklessly. Strong CI/CD, testing culture, and operational maturity mean you can drive rapid iteration without gambling customer trust.

Some Examples of Projects Our Developers Have Recently Completed

• Universal Metadata Extractor: Built a scalable pipeline that extracts and normalizes metadata from dozens of file types so customers can search, tag, and audit files with precision.
• Streaming File Previews: Delivered a system for on-the-fly video and audio previews that stream instantly in-browser.
• Job Orchestration Engine: Built a distributed Ruby job system to handle large-scale, parallel file processing with reliability guarantees.
• Cross-Cloud Automation: Extended our orchestration engine to support real-time workflows across SharePoint, Box, and Google Drive.

Some Projects Our Developers Will Tackle in the Next 6–12 Months

• AI-Powered Content Discovery: Implementing semantic file search using vector embeddings for meaning-based file discovery.
• Zero-Trust File Sharing: Designing ephemeral file access links with advanced device posture and geolocation constraints.
• Next-Gen Sync: Rebuilding our sync layer to support multi-directional, conflict-aware synchronization at petabyte scale.
• Observability at Scale: Rolling out a monitoring framework with distributed tracing for real-time visibility into file flows and API calls.
• Policy as Code: Enabling IT teams to define and enforce security and retention rules in version-controlled code.

What You’ll Actually Do

• Become a domain and customer-workflow expert: Build deep understanding of enterprise file transfer/automation workflows (security, compliance, integrations, reliability) and use that knowledge to guide product decisions.
• Know the competition cold: Maintain an active view of competitor products, patterns, pricing/packaging, and positioning—so Files.com can differentiate intentionally and win with conviction.
• Set strategy, then ship: Translate strategy into a sequenced roadmap, run tight discovery when needed, and drive execution through delivery—making tradeoffs explicit and keeping scope sharp.
• Run the day-to-day execution loop: stay active in GitLab + triage boards, use labels/workflows correctly, keep specs/decisions current, and unblock teams quickly.
• Write exceptional product documentation: Produce clear, structured docs that customers and teammates rely on—requirements, specs, release notes, guides, and decision logs. Treat documentation as part of the product.
• Drive crisp problem definition: Turn ambiguity into alignment: what’s broken, who it impacts, why now, what “good” looks like, and how success will be measured.
• Partner tightly with engineering and design: Work as a true trio to shape solutions that are usable, feasible, and maintainable—while keeping speed high and quality non-negotiable.
• Launch with excellence: Coordinate releases across teams, ensure go-to-market readiness (messaging, enablement, support workflows), and monitor adoption and quality immediately after launch.
• Operate the feedback loop: Use customer conversations, support signals, telemetry, and qualitative feedback to iterate quickly, improve usability, and reduce sharp edges over time.
• Raise the product bar systematically: Identify systemic friction (confusing workflows, missing guardrails, inconsistent patterns) and drive long-term improvements that compound across the platform.

Who Thrives in This Role

• ✅ High-agency builders who want to own outcomes, not outputs.
• ✅ PMs who love enterprise workflows—permissions, auditability, policy, safety, and operational clarity.
• ✅ People who can make tradeoffs explicit and keep teams aligned when reality is messy.
• ✅ Strong writers who treat documentation as a first-class product surface.
• ✅ Domain learners who enjoy mastering a market and using that mastery to differentiate intentionally.
• ✅ Candidates who don’t need a PM title to be great here—strong fits often come from engineering, tech lead roles, solopreneurship, or founding environments where they shipped outcomes end-to-end.

Your Growth Path

Product Managers at Files.com don’t stagnate. Many grow into:

• Product Leadership — owning major product areas and mentoring other PMs.
• Platform Ownership — driving strategy across core systems like identity, policy, audit, and reliability surfaces.
• Full-Stack Product Depth — going deeper into APIs, admin workflows, integrations, and operational tooling.
• Market Leadership — becoming a recognized domain expert and shaping how the industry thinks about file automation.

Perks & Benefits

🩺 100% Paid Health, Dental & Vision (75% for family)
💸 401(k) with 4% Company Match 📈 Equity Grants for Every Employee
🍼 Paid Parental Leave 🌴 20 PTO Days + 11 Holidays + Full Company Winter Break
💰 $1,000 Signing Bonus + Modern Apple Laptop + Anniversary Gifts
✈️ Team Travel to NYC, Austin, Nashville, Miami, and more

👉 Bottom Line: This isn’t “just another PM role.” It’s a career accelerator for high-agency builders who want to master an enterprise domain, work with an engineering-first team, and ship product improvements that customers feel every day. If you want ownership, speed, rigor, and real impact—this is your seat.