Remote IT Director - Cloud, AI & Strategy Leader

Swooped; United States; Remote; USD 150,000 - 210,000; Full time

Benefits offered by this job

Medical, dental, and vision plans

401(k) with company match

Paid time off

Life insurance

Disability and AD&D coverage

Professional development & tuition

Paid parental leave

Job summary

Swooped is seeking an IT Director to lead the information technology function as the company scales into a midsize, technology-driven organization with a fully remote nationwide workforce. You will drive IT strategy, build the internal team, govern platforms and policies, and insource capabilities while guiding AI tool adoption and security governance.

Initially hands-on, the role evolves into strategic leadership and architecture escalations as teams are hired.

Qualifications

• Bachelor’s degree in information systems, computer science, engineering, or related discipline OR Four additional years of hands-on IT, cloud, or software delivery experience.
• Minimum ten years of IT experience, including five to seven years of leadership experience with at least two years leading leads, supervisors, or multiple teams.
• Must have budget or staffing-plan accountability.
• Experience supporting software developers with environments, CI/CD, release, and production support, not only end-user IT.
• Experience building or scaling an internal IT function through rapid growth, ideally from small to midsize, including moving capability in-house from MSP.
• Expert knowledge of Microsoft Azure (landing zones, policy, cost management) and Microsoft 365; Entra ID knowledge; security and governance.

Responsibilities

• Translate company objectives into annual IT plans and multiyear roadmaps; define operating models and manage cloud spend.
• Recruit, coach, and manage IT leads; oversee MSP service levels and transition services in-house.
• Own Azure tenant, landing zones, CI/CD pipelines, container hosting, and infrastructure as code; govern lifecycles.
• Provide secure stacks, licensing, APIs, and access controls for approved AI tools; oversee AI guardrails.
• Establish risk-based IT policies; manage identity and zero-trust via Entra ID; SOC 2 readiness and audits.
• Deliver nationwide service support and automate onboarding/offboarding; drive automation and AI initiatives.

Skills

IT leadership

Budget accountability

Azure

Microsoft 365

CI/CD

Terraform

Containers

AI tooling

SOC 2 readiness

Security frameworks

Vendor management

Remote leadership

MSP management

Entra ID

GitLab

Education

Bachelor’s degree or equivalent

Tools

Azure DevOps

GitLab

Terraform

Bicep

Intune

SharePoint

Teams

Job description

Swooped is seeking an IT Director to lead the information technology function as the company scales into a midsize, technology-driven organization with a fully remote nationwide workforce. You will drive IT strategy, build the internal team, govern platforms and policies, and insource capabilities while guiding AI tool adoption and security governance.

Initially hands-on, the role evolves into strategic leadership and architecture escalations as teams are hired.