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Onboarding Engineer (Remote – U.S.)

📍 Location: Remote (U.S. only)
💼 Type: Full-time
💰 Compensation: $95,000 - $150,000 (subject to qualifications and experience) + equity + premium benefits

At Files.com, the Onboarding Engineer is the architect of first value. You’ll take Fortune 500s, global brands, and fast-scaling enterprises from “contract signed” to “production-grade, mission-critical deployment” — designing secure file workflows, standing up identity, hardening networks, integrating APIs, and proving ROI fast.

This is not “walk them through a checklist.” It’s deep, hands-on engineering with customers’ IT teams. You’ll wire up SAML/OIDC/SCIM with Okta or Azure AD, script automations with our API and webhooks, and unblock gnarly firewall and proxy issues — all while teaching best practices that stick.

And you do it with real engineering backing. Bugs don’t languish here; fixes ship in days, not quarters. Your feedback lands directly with Product & R&D — which means you implement with confidence, not caveats.


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.

We’ve built a $35M+ business with just 70 people by hiring smart, clear-thinking communicators who act fast and own outcomes. Backed by $46.5M from Riverwood Capital, we’re scaling intentionally—and this role is a core part of that growth.


Why This Role Is Different

  • Onboarding as an engineering discipline: You’ll design production architectures: SSO, RBAC, data flows, automation triggers, IP allowlists, encryption at rest/in transit, audit pipelines — the works.
  • Enterprise surface area, real technical depth: SFTP/FTPS/HTTPS, PGP, REST APIs, webhooks; IdPs (Okta, Azure AD, AD FS, LDAP), key management, least-privilege RBAC; hybrid networks, reverse proxies, TLS, DNS, NAT, egress controls; storage integrations (S3/Blob), SharePoint/OneDrive connectors — you’ll touch them all.
  • Prevent, don’t just resolve: Support fixes after the fact. Onboarding eliminates friction up front: migration plans, throughput testing, cutover playbooks, rollback strategies, observability from day one.
  • A product you’re proud to implement: Files.com powers mission-critical workflows at global scale. You’ll implement a platform that’s fast, reliable, and secure — not build workarounds for “known issues.”


What You’ll Actually Do

Design production-ready deployments

  • Map requirements into robust architectures: identity, access, encryption, automation, retention, and auditability.
  • Author cutover plans with throughput targets, back-pressure handling, retry logic, and verification (checksums, manifests).

Implement identity & access correctly

  • Stand up SAML/OIDC SSO with Okta/Azure AD; configure SCIM for lifecycle provisioning.
  • Model least-privilege RBAC, groups/roles, device/IP policies, and MFA posture.

Integrate and automate

  • Connect storage backends (e.g., S3/Blob), enterprise systems, and endpoints.
  • Use our REST API and webhooks to build event-driven automations; script glue in Python/PowerShell/Bash when needed.

Harden the network path

  • Work through real-world constraints: egress proxies, TLS versions/cipher suites, DPI/IDS appliances, MTU/path issues, DNS/CAA/CAA misconfigurations, and IP allowlists.
  • Validate performance end-to-end: parallelism, window sizes, chunking, and timeouts.

Teach, document, and scale

  • Run admin training and technical handoffs; produce crisp diagrams, runbooks, and KB articles.
  • Feed patterns back to Product & Engineering; turn one-off fixes into repeatable playbooks.


The Kinds of Problems You’ll Tackle Every Week

  • SAML assertion bugs (NameID/ACS mismatch, clock skew) and OIDC scope/claim mapping.
  • SCIM drift detection, deprovisioning safety, and group-driven role assignment.
  • SFTP/FTPS tuning across high-latency links; negotiating ciphers/MACs; passive mode firewall pinholes.
  • Proxy/TLS handshake failures (SNI, intermediate certs, mTLS); rotating keys/certs without downtime.
  • Event-driven pipelines with webhooks, retries, idempotency keys, and dead-letter strategies.
  • Bulk migrations: parallel workers, rate limiting, checksum validation, and resumable transfers.
  • Building observability from day one: audit streams, SIEM forwarding, and success SLOs.


What Success Looks Like

  • Production deployments shipped on schedule with zero “failed launches.”
  • Adoption curves that climb in the first 30–90 days: usage, automations, departments onboarded.
  • Security posture locked: SSO/SCIM live, RBAC least-privilege, audit forwarding enabled.
  • Throughput targets met or exceeded with documented performance baselines and runbooks.
  • Expansion signals identified early via consultative discovery (more sites, features, or storage).
  • Playbooks created that the next Onboarding Engineer (or customer admin) can reuse verbatim.


Who Thrives in This Role

  • ✅ You think like an engineer and a consultant: deep systems knowledge + crisp customer communication.
  • ✅ You’re fluent in at least several of: SAML/OIDC/SCIM, SFTP/FTPS/HTTPS, TLS & PKI, REST/webhooks, Python/PowerShell/Bash, IP networking, proxies/firewalls.
  • ✅ You enjoy live debugging over Zoom as much as writing a clean, reusable runbook after.
  • ✅ You anticipate failure modes and design guardrails so they never reach production.
  • ✅ You’re remote-savvy: strong async notes, tight agendas, excellent ownership.


Where This Role Can Take You

  • Onboarding → Product / Platform (shape the roadmap with customer patterns)
  • Onboarding → Customer Success / Strategic Accounts (own long-term outcomes)
  • Onboarding → Team Lead / Manager (scale the craft across the org)

Your trajectory is limited only by your clarity, discipline, and output.


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: If you want a remote role where you’ll do real engineering with enterprise IT — designing identity, securing networks, integrating APIs, and launching mission-critical workflows — this is your seat. Onboarding at Files.com is where technical craft meets customer impact.

We would like you to tell us why this opportunity speaks to you. You don’t have to tell us now, but we promise we’ll read your story upfront. You’re more than a resume!

"You're surrounded by intelligent and driven people who genuinely want to see you succeed. Everyone here is invested in helping you grow and perform at your best. It's rare to find that combination of high talent and supportive culture in one place."

— Karan Mangat, Account Executive

“It's really about being able to work with really smart people on really interesting problems and feeling like you're actually contributing to something big.”

— Gabe Purrenhage, Principal Infrastructure Engineer

“Files.com gives me opportunities to solve big problems, build real products, and see the direct impact on customers and growth. It’s work that truly matters.”

— Dustin Zeisler, Principal Engineer

"The level of excellence across the team encourages me to keep learning, try new ideas, and become better at what I do. I also appreciate how quickly our products move from concept to real customer use. Seeing something you helped build get adopted almost immediately creates a strong sense of pride and connection to the work."

— Claudio Tinnirello, Product Manager

"I am truly proud to work for Files.com. We’re creating technology that genuinely helps people. You can see your work go from idea to impact so quickly, it's awesome."

— Jesse Harris, Senior Engineering Manager