IT Systems and Automation Engineer

Skills

About the Role

You will own day to day end user support across hardware, software, accounts and access requests, acting as the primary point of contact through the helpdesk and Slack. You'll run full IT onboarding and offboarding, manage IT assets and inventory, and improve and document IT processes to reduce recurring ticket volume. You'll manage the SaaS portfolio and lead vendor management and security reviews. You'll also own onsite IT, networking and AV across all offices. Beyond support, you will design and build automation that eliminates manual toil across IT, HR and security, ranging from simple scripts to agentic AI workflows. You'll architect and operate identity lifecycle automation in Okta and Okta Workflows, write scripts and integrations in Python and JavaScript, and build AI assisted helpdesk deflection flows. You will document your automation processes and system architecture thoroughly. On the security and compliance side, you will support SOC 2 Type II, PCI DSS and GDPR efforts, help enforce endpoint and access security, and assist with security alert triage and incident response.

Requirements

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

Responsibilities

• 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.
• 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.
• 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.
• 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.
• 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.

Benefits

• Unlimited time off with a 10 day minimum
• Flexible working, including work from home or office options
• Home office stipend for new hires
• Comprehensive health, dental and vision plans for employees and dependents
• 100% company subsidized life insurance plan
• 401(k) with a 4% company match
• Equity option plan
• Rain Card for testing company products
• Health and wellness spending allowance
• Team summits and company offsites