Position Summary

The Director of IT Operations & Security is the organization's technology infrastructure and security thought leader - accountable for the vision, strategy, and execution of a resilient, secure, AI-enabled technology environment that scales with a national footprint.

This is not a keep-the-lights-on role. The organization runs a hybrid model of internal staff and large-scale managed service provider (MSP) partnerships - including service desk, security operations, and device-as-a-service - and this leader owns the strategy, performance, and economics of those partnerships. A core mandate of the role is using AI and automation to streamline IT service delivery, reduce cost, and improve organizational margin, while continuously raising the bar on security posture and employee/student technology experience.

The ideal candidate combines deep technical credibility with genuine external-facing vendor leadership: someone who has negotiated and managed multiyear, large-scale MSP contracts, modernized legacy environments, and can speak with authority to the CIO and Executive Team about where infrastructure and security are headed next.

This is a hybrid role requiring regular in-person engagement. Applicants must live within a reasonable commutable distance to a Year Up United location.

In keeping with Year Up United's values, this leader also can engage directly with students as a mentor and advocate.

What You'll Do

Strategic Leadership & Innovation

• Own the strategic vision and multi-year roadmap for infrastructure, service delivery, and security across a national, 20+ location organization
• Serve as the organization's internal thought leader on emerging infrastructure, security, and AI/automation trends - translating them into practical roadmap decisions
• Identify and lead AI- and automation-driven initiatives that streamline IT operations, reduce vendor and support costs, and improve organizational margin
• Support the CIO in preparing executive and Board-level briefings on security posture, technology strategy, and major infrastructure investments
• Partner with the Senior Director of IT Architecture & Applications to align infrastructure and cloud strategy with application and platform roadmaps

Vendor & Managed Services Leadership

• Own strategy, performance, and economics for all outsourced infrastructure and security services - including service desk, security operations center (SOC), device-as-a-service (DaaS), network management, and data center services
• Partner with the CIO on contract negotiation, renewal, and governance for multiyear, large MSP engagements, holding vendors accountable to SLAs/OLAs and driving continuous improvement
• Serve as the accountable technical and business owner of ServiceNow, including platform strategy, roadmap, and the vendor relationship supporting it
• Build and manage a portfolio approach to vendor relationships that balances cost, quality, and scalability as the organization grows

Security & Risk

• Direct internal and external (MSP-delivered) security operations to continuously mature Year Up United's security posture, using the CIS Controls as a baseline framework
• Own the organization's incident response program and serve as escalation point for high-severity security events
• Partner with senior leadership and Legal, as part of the Enterprise Risk Committee, to develop and maintain security policy
• Provide written quarterly security program updates to the CIO in support of executive briefings to the Board of Directors
• Ensure technology and business processes meet applicable privacy and compliance requirements (e.g., FERPA)

Team Leadership & Development

• Lead, mentor, and develop a team of 5 direct reports across infrastructure, service delivery, and security, plus indirect leadership of MSP-supplied resources
• Set clear goals, accountabilities, and development plans; build bench strength and succession depth on the team
• Foster a culture of ownership, customer service, and continuous improvement

Service Delivery & Customer Experience

• Own service levels and customer satisfaction for infrastructure, security, and support delivery across ~600 staff, thousands of students, and 20+ physical and virtual locations
• Drive root-cause problem management and preventive action across recurring issues
• Serve as executive escalation point for business-impacting incidents, including off-hours as needed
• Lead automation initiatives that improve the employee and student technology experience while reducing manual support burden

Learning Community

• Serve as a coach/mentor to a small group of current students
• Participate in weekly group sessions, staff meetings, and training as part of the broader Learning Community

What You'll Bring

Required

• 10+ years of progressive IT infrastructure/operations experience, including 5+ years in senior IT leadership managing multiple teams
• Demonstrated experience owning large-scale managed service provider relationships (service desk, security, infrastructure, or device-as-a-service) including contract negotiation and vendor performance management
• Hands-on experience using AI or automation tools to streamline IT service delivery, reduce cost, or improve operational margin
• Deep expertise in ServiceNow platform ownership and strategy
• Strong understanding of modern cloud environments (AWS and/or Azure), identity (Okta/Active Directory), and multi-location network and security architecture
• Track record of leading significant infrastructure initiatives on time and on budget (cloud migrations, data center consolidation/relocation, voice/UC modernization)
• Ability to translate business requirements into scalable technology solutions and communicate them credibly to the CIO and executives
• A passion for the mission of Year Up United and belief in the potential of young adults navigating the Opportunity Divide

Preferred

• Experience in nonprofit, education, or workforce development environments
• Relevant certifications: CISSP, CISM, ITIL v4; PMP a plus
• Familiarity with modern endpoint and device-as-a-service management (Intune, Jamf, or equivalent)
• Exposure to Zero Trust architecture and cloud cost/FinOps optimization
• Prior experience presenting directly to a CIO and/or executive committee

Additional

• Occasional travel to organizational sites; occasional lifting of equipment (up to 50 lbs) during data center or site work
• Ability to work occasional off-hours for planned maintenance or high-severity escalations

Salary Range: $140,000 - $160,000

#LI-Hybrid

WORKING AT YEAR UP UNITED:

Starting January 5, 2026, employees are expected to work on-site at least two days per week (Monday through Thursday dependent on job requirements). To be eligible for employment, candidates must live and work in a state (or an approved proximate state*) where Year Up United operates. For a list of eligible locations, please visit: https://www.yearup.org/job-training/locations

*Approved proximate states where Year Up United operates are: Connecticut, Indiana, New Hampshire, New Jersey, South Carolina and Virginia.

COMPENSATION & BENEFITS:

• Year Up United has established salary ranges for each of our sites, which allows us to pay employees competitively, equitably and consistently in different geographic markets. For roles in which the location is listed as flexible, the range displayed reflects the minimum and maximum target for new hire salaries for the position across all US locations. Salary offers take into account a candidate's skills, experience, and location. Your recruiter can share more about the specific salary range for your location during the hiring process.
• Benefits: Comprehensive healthcare options and dental coverage; 401(k) match for eligible participants.
• Vacation: Earn three weeks paid vacation in first year of employment; four weeks after initial year.

** This is an exempt role (paid on a salaried basis). **

TO APPLY:

Please submit a thoughtful cover letter and resume through our website.

We respectfully request no phone calls.