Vice President Information Technology Services

Founded in 1969, Pine Street Inn (PSI) serves homeless individuals by providing the full spectrum of services to help homeless individuals reach their highest level of independence and get back to a place they can call home.

Founded in 1969, Pine Street Inn (PSI) serves homeless individuals by providing the full spectrum of services to help homeless individuals reach their highest level of independence and get back to a place they can call home.

Pine Street Inn collaborates with homeless individuals to help them move from the streets and shelter to a home and assists formerly homeless individuals in retaining housing. We provide street outreach, emergency services, supportive housing, job training and connections to employment. We tirelessly advocate for collaborative solutions to end homelessness.

Pine Street Inn seeks an experienced, mission-driven technology executive to serve as Vice President of Information Technology Services. This senior leadership role owns the full IT operating budget, department structure, staffing, vendor relationships, security posture, and service delivery for a team of approximately 13 IT professionals spanning infrastructure, security, applications, and end-user support across a multi-site nonprofit environment.

The VP carries executive accountability for Pine Street Inn's 3-year ITS strategic plan and for making sure technology reliably supports shelter, housing, outreach, and administrative operations every day. Artificial intelligence is a core, ongoing component of that strategy: the VP sets direction, prioritizes AI use cases, establishes responsible-use guardrails, and drives adoption in partnership with Programs, Fundraising, and Administrative leaders.

Reporting to the Chief Financial Officer, the VP represents technology strategy and performance to executive leadership and the Board Members.

Schedule: Monday - Friday (hybrid on-site 3x/week Hours: 40 hours per week; 9:00 a.m.

- 5:00 p.m.

On Call: Periodic on-call availability for critical system incidents

Office: On-site at Pine Street Inn's Boston campus, with travel to program sites as needed

Required Education/ Training

• Bachelor's degree in information technology, Computer Science, or a related field.

Preferred Education/ Training

• Advanced degree, and/or professional certification such as CISSP, PMP, ITIL, TOGAF, or other recognized Information Technology Certification.

Required Physical& Mental Abilities/Skills

• Ability to work at a computer for extended periods and participate in frequent meetings, including with executive leadership and the Board.
• Ability to travel periodically between Pine Street Inn program sites across the Boston area.
• Ability to respond to critical system incidents outside of standard business hours as needed.

Strong analytical and problem-solving skills, with the ability to manage multiple priorities in a fast-paced environment.

Requirements

ESSENTIAL FUNCTIONS INCLUDE BUT ARE NOT LIMITED TO:

Department Leadership & Team Management

• Leads, manages, and grows the IT department (~13 staff), including infrastructure/network engineers, systems administrators, application/support analysts, security staff, and helpdesk personnel.
• Owns the department's organizational structure - defines roles, reporting lines, career paths, and succession plans - to ensure the team is staffed and structured to meet organizational needs.
• Hires, onboards, coaches, and manages the performance of IT staff and managers; sets clear goals and keeps the team accountable to service standards.
• Builds a culture of accountability, collaboration, continuous learning, and service excellence within the department.
• Conducts regular 1:1s, team meetings, and performance reviews; identifies and develops future IT leaders from within the team.
• Manages department workload and prioritization across competing operational and project demands.

IT Operations & Infrastructure

• Owns the reliability, security, and performance of Pine Street Inn's full technology - network, servers, cloud services, endpoints, telephony, and applications - across all program sites.
• Ensures robust helpdesk and end-user support operations, with clear SLAs, ticketing processes, and a strong customer-service orientation toward program and administrative staff.
• Directs infrastructure upgrades, system migrations, and technology deployments, minimizing disruption to shelter, housing, and administrative operations.
• Owns business continuity and disaster recovery planning for all critical systems and data.
• Establishes and enforces IT governance policies, standard operating procedures, and change-management practices across the department.

Budget, Vendors & Financial Management

• Develops, owns, and manages the annual IT capital and operating budgets; forecast spend, track variances, and report regularly to the CFO.
• Identifies cost-optimization opportunities across software licensing, infrastructure, and vendor contracts.
• Negotiates and manage relationships with IT vendors, managed service providers, telecom…