📍 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.
Top Skills
What We Do
Files.com is a SaaS file automation and integration platform that enables organizations to securely transfer, share, and store files between users, teams, and organizations
Why Work With Us
At Files.com, we build technology so businesses can manage file transfer and security at scale. We are private equity backed, profitable, and lead our industry in terms of revenue per employee. This means that each and every team member is able to have a high degree of direct responsibility and impact.
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