Senior IT Operations Engineer

What you'll do

IT support, Services and Vendor management

• Own day to day end user support across hardware, software, accounts and access requests, serving as the primary point of contact through Console helpdesk and Slack.
• Run full IT onboarding and offboarding, including device provisioning through JumpCloud and Apple Business Manager, account setup and the new hire IT and security session.
• Own IT asset and inventory management across all offices, tracking hardware through its full lifecycle from procurement and assignment to refresh and retirement, with an accurate inventory.
• Improve and document IT processes, including workflows, runbooks and onboarding guides, and drive down recurring ticket volume.
• Manage the SaaS portfolio, including licenses, renewals, enterprise tier upgrades and rightsizing spend.
• Lead vendor management and vendor security reviews, evaluating new tools, negotiating pricing and terms and onboarding approved vendors.
• Own onsite IT, networking and AV across all Rain offices, including UniFi network management, conference room infrastructure and physical security systems.

Automation, agentic AI and identity engineering

• Design and build automation that eliminates manual toil across IT, HR and security, from simple scripts to agentic AI workflows.
• Architect and operate identity lifecycle automation in Okta and Okta Workflows, including joiner mover leaver provisioning and instant deprovisioning across the SaaS stack.
• Write and maintain scripts and lightweight internal integrations in Python and JavaScript to connect platforms that lack native integrations.
• Build AI assisted helpdesk deflection and self service flows that resolve common requests automatically and route the rest with context attached.
• Identify high leverage automation opportunities and ship reliable, monitored solutions with proper error handling and alerting.
• Document all automation processes, system architecture and Okta configurations thoroughly so the work is maintainable and knowledge transfers cleanly.

Security and Compliance

• Support SOC 2 Type II, PCI DSS and GDPR efforts, including evidence collection, access reviews and control monitoring using tools such as Vanta.
• Help enforce endpoint and access security across CrowdStrike, JumpCloud and Okta, including device posture and conditional access.
• Assist with security alert triage and incident response in coordination with the IT Manager.

You are likely to succeed if you have:

• 3 or more years in IT support, IT systems engineering or automation engineering, ideally at a startup or hypergrowth company.
• Hands on Okta administration experience, including SSO, MFA, Group Rules and Universal Directory, with Okta Workflows a strong plus.
• Scripting and automation proficiency in Python and JavaScript for API interaction and system management.
• Familiarity with a modern SaaS and endpoint stack such as Google Workspace, Slack, JumpCloud, CrowdStrike and more.
• Hands on experience with office networking and AV such as UniFi, and comfort supporting onsite infrastructure across multiple offices.
• A working understanding of compliance frameworks such as SOC 2, PCI DSS and GDPR and how IT controls map to them.
• Strong end user support instincts and excellent written and verbal communication.
• A bias toward action and genuine comfort wearing many hats and filling gaps across corporate IT and security on a small team.

Nice to have:

• Experience in fintech, payments or another regulated and high compliance environment.
• Experience with agentic AI tools and building AI powered internal workflows.
• Vendor negotiation and SaaS cost optimization experience.

Things that enable a fulfilling, healthy and happy experience at Rain:

Unlimited time off 🌴 Unlimited vacation can be daunting, so we require Rainmakers to take 10 days minimum for themselves.

Flexible working ☕ We support a flexible workplace – work from home, come into an office, or both. We want everyone to work in an environment where they're their most confident and productive selves. New Rainmakers receive a stipend to set up a comfortable home workspace.

Easy to access benefits 🧠 For US Rainmakers, we cover 95% of your health, dental, and vision plan costs and 90% for your dependents, plus a 100% company-subsidized life insurance plan.

Retirement goals 💡 Plan for the future with confidence. We offer a 401(k) with a 4% company match.

Equity plan 📦 Every Rainmaker gets an equity option plan so we all benefit from our success.

Health and Wellness 📚 High performance begins from within. Rainmakers receive a monthly stipend to be used for eligible health and wellness spending like gym memberships/fitness classes, massages, acupuncture - whatever recharges you!

In-office meals 🍜 Rainmakers working from the office enjoy lunch and dinner on us, covered with a DoorDash credit.

Team summits ✨ Summits play an important role at Rain. Time together helps us build relationships and a common destiny. Expect team and company offsites, both domestic and international.