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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.

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 carriers, and software partners, holding them accountable to scope, quality, and cost commitments.

• Evaluates build-vs-buy and in-house-vs-outsourced decisions for tools, platforms, and services.

Security, Risk & Compliance

• Owns the organization's cybersecurity program, including policies, standards, monitoring, and incident response.

• Maintains compliance with applicable data privacy and security requirements, including HIPAA awareness given the nature of client data.

• Establishes and maintain data governance standards — data ownership, access controls, retention, and quality — across all systems.

• Reports on risk posture, security incidents, and compliance status to the CFO and executive leadership.

Strategic & Executive Leadership

• Owns execution of Pine Street Inn's 3-year ITS strategic plan, translating approved roadmap priorities into actionable project plans with defined timelines, owners, milestones, and success metrics.

• Develops and maintains a multi-year IT roadmap aligned to Pine Street Inn's mission and organizational priorities, revisiting it regularly to reflect changing needs, funding, and technology.

• Maintains project governance across all strategic-plan initiatives — tracking deliverables, managing dependencies, and surfacing risks and mitigation options to the CFO and executive leadership in a timely manner.

• Sequences and prioritizes roadmap initiatives against department capacity and organizational readiness, adjusting timelines as needs, funding, or staffing shift.

• Ensures all strategic plan initiatives are executed within approved budget parameters, providing regular financial reporting to the CFO on spending, projections, and variances.

• Serves as a member of the senior leadership team, partnering with the CFO and other executives on technology-related planning and decision-making.

• Represents IT department performance, strategic-plan progress, priorities, and budget in leadership meetings, Board updates, and funder conversations, translating technical topics for non-technical audiences.

• Works effectively within Pine Street Inn's nonprofit operating environment, understanding grant-funded constraints, restricted budgets, and donor accountability requirements.

• Collaborates with Finance, Development, Programs, and HR leadership to ensure IT plans and resources are coordinated with organization-wide priorities.

AI Strategy & Implementation

• Serves as the organization's executive owner of AI strategy, championing AI as a critical, ongoing capability for advancing Pine Street Inn's mission.

• Identifies, prioritizes, and oversees the implementation of AI tools and use cases across programs, fundraising, and operational functions.

• Establishes and maintains the organization's AI ethics and equity policy, with particular attention to initiatives affecting client-facing services.

• Leads staff training, change management, and adoption support for every AI rollout, working with department managers to ensure sustained, responsible use.

• Monitors the performance and effectiveness of AI vendors and tools post-deployment, adjusting course as needed.

Stays current on emerging AI and technology trends relevant to the nonprofit human-services sector, advising the CFO and executive leadership on opportunities and risks.