IT Director

We are an insurance services firm processing hundreds of thousands of audits annually for our clients. We are in the midst of a pivotal transformation: replacing our legacy C++ application hosted on AWS with a modern, AI-native platform that embeds artificial intelligence throughout our audit workflows, client deliverables, and billing operations.

We’re looking for an IT Director who can own this transformation end-to-end. This is a hands-on leadership role for someone who is equal parts cloud architect, AI practitioner, software-savvy infrastructure leader, and people-first technology partner to our ~135 auditors. You won’t just keep the lights on - you’ll design the systems that power our next decade of growth.

What You’ll Own

Cloud & Application Infrastructure. Architect, manage, and optimize our cloud environment across AWS and Azure. Lead the migration away from our aging C++ system and stand up the infrastructure backbone for our new AI-powered audit platform. Make smart build-vs-buy decisions, manage costs, and ensure security, reliability, and scalability as we process audits at high volume.

AI Systems & Integration. Serve as the technical owner of our AI stack - OpenAI, Azure AI services, and the orchestration layers, vector databases, and integration tooling that connect them to our internal application. Partner with our development team to embed AI into audit processing, client deliverable generation, and billing workflows. Stay ahead of a fast-moving field and bring practical recommendations to leadership.

Software Development Partnership. Work shoulder-to-shoulder with engineering on our new platform. You don’t need to write production code daily, but you should be fluent enough to review architecture, debate trade-offs, and unblock technical decisions. Own the infrastructure, CI/CD, environments, and observability that let developers ship quickly and safely.

Operations at Scale. Ensure our platform reliably processes hundreds of thousands of audits per year, delivers them to clients on time, and supports accurate, automated billing. Establish SLAs, monitoring, incident response, and disaster recovery practices appropriate for a business where client trust depends on uptime and accuracy.

End-User Support & Enablement. Be a proactive technology partner to ~135 auditors. Own laptop fleet management, identity and access (SSO, MFA), collaboration tooling, onboarding/offboarding, and day-to-day support. Build a service culture where auditors feel supported, not blocked. You’ll have budget to hire support staff to scale this function as the team grows.

Security, Compliance & Risk. Own information security for a firm handling sensitive client and insurance data. Implement and maintain controls appropriate for our regulatory environment (SOC 2 readiness, data handling, vendor risk, etc.), and lead the response when issues arise.

Team Building. Hire and develop a small, high-leverage IT team - likely starting with a help-desk/support hire to free you up for higher-order architectural work.

Do you have experience in Team management?, * 8+ years in IT, infrastructure, or platform engineering, with at least 3+ in a leadership role

• Deep, hands-on experience with both AWS and Azure - not just one
• Practical experience building or operating systems that use OpenAI APIs or comparable LLM platforms in production
• Strong software development background; comfortable reviewing code, debating architecture, and partnering with engineering teams
• Track record running production systems at meaningful scale, with real ownership of uptime, cost, and security
• Experience managing end-user IT for a distributed workforce (laptops, identity, SaaS sprawl, support workflows)
• Excellent judgment on when to build, when to buy, and when to wait - especially in the rapidly evolving AI space
• Comfort operating in a small-to-mid-size company where you’ll wear many hats and make decisions with incomplete information
• Strong communicator who can translate between executives, developers, and non-technical end users

Nice to Have

• Experience in insurance, financial services, audit, or another regulated industry
• Background migrating off legacy systems (especially older C/C++ codebases)
• SOC 2, HIPAA, or similar compliance program experience
• IaC fluency (Terraform, Bicep, CloudFormation) and modern observability tooling

Pulled from the full job description

• 401(k)
• Health insurance
• 401(k) matching
• Vision insurance
• Dental insurance
• Flexible schedule, * 401(k)
• 401(k) matching
• Dental insurance
• Flexible schedule
• Health insurance
• Vision insurance