[Hiring] Director of Information Technology @The Redesign Group

Role Description

The Redesign Group is seeking a Director of Information Technology to own our internal technology estate end to end and lead the team that runs it. This role reports directly to the Chief Information Officer and covers identity, endpoints, networking, collaboration, service management, and our internal AI platform across a remote-first organization.

Our clients hold us to a high standard for the infrastructure we design and secure on their behalf. This role exists to hold our own environment to that same standard. You will set the internal technology strategy, build and develop the team that executes it, and own the internal adoption and governance of AI so that our own practice sharpens what our AI and security teams deliver to clients.

This position is designed for a leader who has built and scaled internal technology through fast growth — someone equally comfortable writing a three-year roadmap and resolving a production identity issue in the first year. You will work closely with Security, Engineering, Finance, and HR, and you will manage the vendor and managed-service relationships that extend the team.

Qualifications

• 10+ years of information technology experience, including years leading teams or owning a technology function
• Proven experience building and scaling internal IT in a distributed or remote-first company through a period of fast growth
• Experience presenting technology strategy, investment recommendations, risks, and operating metrics to executive leadership
• Deep hands-on experience with Microsoft 365 and Entra ID, endpoint management (Intune or equivalent), and SaaS administration at scale
• Demonstrated ownership of internal AI adoption and governance, including policy, data handling, and change management
• Strong security fluency — able to partner credibly with a CISO and translate risk into business terms for executive stakeholders
• Experience operating in a solutions provider, MSP, or consulting environment strongly preferred
• Experience supporting audit, SOC 2, or other regulated compliance requirements
• Vendor, MSP, and contract negotiation experience with budget ownership
• Ability to communicate technical trade-offs clearly to both technical and executive audiences, in writing and in person
• Relevant industry certifications such as ITIL, Microsoft, CISSP/CISM, PMP, or equivalent are valued but not required

Requirements

• Build and run a multi-year internal technology roadmap across identity, endpoints, networking, collaboration, and service management
• Tie every investment to a business outcome, with defined success measures rather than product categories
• Define what is run internally versus delivered through partners and managed service providers
• Establish IT governance, standards, architecture review, and change management
• Design the internal IT function, build the business case for headcount, and hire against it
• Develop and mentor the team; establish clear ownership, on-call, and escalation models
• Build the internal service catalog and the service levels behind it
• Own internal AI tool use case development, rollout, training, and adoption measurement
• Partner with the Redesign AI practice so internal use informs client-facing delivery
• Apply financial engineering to the internal AI estate — build the unit-cost model, forecast consumption, negotiate commitments and reserved capacity, and hold AI spend accountable to measured productivity gains
• Own endpoint management, configuration baselines, patching, and device lifecycle (Intune or equivalent)
• Manage the Microsoft 365 collaboration estate, including Teams, SharePoint, and Exchange governance
• Define and enforce device posture requirements for a remote-first workforce
• Own internal network architecture, remote access, and secure connectivity models
• Manage internal cloud and hosting footprint, including capacity, cost, and resilience
• Own backup, recovery, and business continuity for internal systems, with tested recovery objectives
• Stand up and mature IT service management — intake, incident, problem, request, and change
• Publish operational metrics and remove the largest sources of employee friction each quarter
• Own onboarding and offboarding technology experience in partnership with HR
• Own the internal IT budget, forecast, and software license position
• Rationalize the SaaS estate and manage renewals, negotiations, and contract terms
• Hold partners and managed service providers accountable to defined service levels
• Partner with security leadership and own the IT execution half of the security program
• Support SOC 2 and ISO audit readiness, including evidence collection and control operation
• Own vulnerability management and remediation for internal systems and endpoints

Benefits

• Medical Insurance
• Dental Insurance
• Vision Insurance
• 401(k) retirement plan with company match (annual dollar cap applied)
• Flexible time off plan
• 15 paid holidays
• Sick leave (amount varies by state requirements and is at least the minimum required by any state)
• Short-term and long-term disability
• Life insurance
• Paid parental leave

This position is eligible for discretionary incentive compensation and/or bonus opportunities based on individual and company performance.

We’re an Equal Opportunity and Affirmative Action Employer and welcome applicants from all backgrounds. We consider qualified candidates without regard to any legally protected status. This role is subject to applicable employment laws based on work location. In compliance with pay transparency laws, the compensation range for this role is included, with final pay based on experience, skills, and location. We participate in E-Verify to confirm employment eligibility and are happy to provide reasonable accommodations throughout the hiring process—just let us know how we can help.