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Title: Senior Director of ITS & AI Strategy Implementation

Days/Hours: 40 hours, Monday - Friday 9:00 a.m. – 5:00 p.m.
Reports to: ITS Director (operational/technical) & Chief Financial Officer (strategic initiative oversight)
Location: 444 Harrison Avenue, Boston, MA 02118

About Pine Street Inn

Pine Street Inn is New England’s largest provider of services to individuals experiencing homelessness. Founded in 1969, we serve more than 2,000 people each day through emergency shelter, permanent supportive housing, street outreach, and employment and workforce development programs. Our mission is to provide a compassionate and safe environment, as well as essential services, to homeless individuals while supporting each person’s movement toward self-sufficiency and more stable lives.

Pine Street Inn is committed to using technology as a strategic lever in advancing our mission — improving service delivery, strengthening operational efficiency, and enabling data-driven decision-making across all of our programs.

Position Overview

Pine Street Inn seeks an experienced and mission-driven Senior Director of ITS & AI Strategy Implementation to lead the execution of our completed ITS and AI strategic plans. This is a senior leadership role focused on implementation, not plan development — the strategies are in place, and we need a skilled facilitator to bring them to life.

Reporting to the ITS Director for operational and technical matters and to the Chief Financial Officer for strategic initiative oversight, this position serves as the primary driver of both plans simultaneously. The Senior Director will work in close partnership with the ITS Director, CFO, and an external project management consultant, ensuring that initiatives are delivered on time, within budget, and in a way that meaningfully advances Pine Street Inn’s mission.

The ideal candidate combines deep technical knowledge with strong program management skills, financial fluency, and interpersonal effectiveness to lead change in a complex, multi-site nonprofit environment.

Key Responsibilities

ITS Strategy Implementation

• Lead the implementation of Pine Street Inn’s ITS strategic plan, translating approved roadmap priorities into actionable project plans with defined timelines, owners, milestones, and success metrics.

• Coordinate with the external project management consultant to maintain project governance, track deliverables, manage dependencies, and surface risks to the ITS Director and CFO in a timely manner.

• Oversee infrastructure upgrades, system migrations, and technology deployments in alignment with the approved roadmap, ensuring minimal disruption to shelter, housing, and administrative operations.

• Manage IT vendor relationships and contracts, holding external partners accountable to scope, quality, and timeline commitments.

• Ensure all ITS initiatives are executed within approved budget parameters and provide regular financial reporting to the CFO on spend, projections, and variances.

• Maintain and enforce IT governance policies, security standards, and compliance requirements across all implementation activities.

• Serve as a bridge between technical execution and organizational communication, keeping program and administrative leaders informed of progress, changes, and impacts.

AI Strategy Implementation

• Drive execution of Pine Street Inn’s AI strategic plan, coordinating with the ITS Director, CFO, and external consultant to sequence and deliver approved AI initiatives on time and within budget.

• Manage the rollout of prioritized AI tools and use cases across program, fundraising, and operational functions, ensuring each deployment is preceded by adequate staff preparation and support.

• Oversee implementation of the organization’s data governance framework, working with department leaders to establish data ownership, access protocols, and quality standards required to support AI initiatives.

• Monitor AI vendor performance and tool effectiveness post-deployment, providing the ITS Director and CFO with regular status updates and recommendations for adjustment.

• Lead staff adoption efforts in coordination with department managers, ensuring training, change management, and ongoing support are embedded in every AI rollout.

• Maintain adherence to the organization’s AI ethics and equity policy throughout all implementation activities, with particular attention to initiatives that affect client-facing services.

ITS Environment & Operations

• Develop a deep working knowledge of Pine Street Inn’s full technology environment — systems, data flows, vendor relationships, staff capacity, and site-specific needs — as a foundation for effective implementation leadership.

• Partner with the ITS Director on day-to-day operational priorities, providing senior-level support on escalated issues, staffing needs, and cross-functional coordination.

• Support the ITS team’s professional development, fostering a culture of accountability, learning, and service excellence as new systems and tools are introduced.

• Identify operational gaps or risks surfaced during implementation and escalate recommendations to the ITS Director and CFO with proposed solutions.

• Maintain documentation on all implementation activities, system changes, and project outcomes to support continuity, audits, and future planning.

Reporting, Collaboration & Nonprofit Context

• Provide structured progress reporting to both the ITS Director and CFO, with reporting cadence and format defined in coordination with both leaders and the external consultant.

• Work effectively within Pine Street Inn’s nonprofit operating environment, demonstrating an understanding of grant-funded project constraints, restricted budgets, and donor accountability requirements.

• Collaborate with finance, development, program, and HR leadership to ensure ITS and AI implementation activities are coordinated with organizational priorities and schedules.

• Represent ITS implementation progress in leadership meetings, board updates, and funder conversations as needed, with the ability to communicate technical content clearly to non-technical audiences.

Knowledge/Experience

• 8+ years of progressive IT experience, with at least 3 years in a senior implementation, program, or project leadership role involving large-scale technology initiatives.

• Demonstrated success executing technology and/or AI strategic plans in a complex, multi-site organization; nonprofit experience strongly preferred.

• Proven ability to manage multiple concurrent initiatives in partnership with external consultants and cross-functional internal stakeholders.

• Strong financial acumen, including experience managing technology budgets and reporting to senior finance leadership.

• Excellent communication and relationship-building skills, with the ability to operate effectively across a dual-reporting structure and engage credibly with both technical and non-technical audiences.

• Familiarity with data governance, cybersecurity frameworks, and applicable compliance requirements; HIPAA awareness a plus given the nature of Pine Street Inn’s client data.

• Bachelor’s degree in information technology, computer science, or a related field required; advanced degree or certifications (PMP, ITIL, CISSP) preferred.

• Deep commitment to Pine Street Inn’s mission and values, and an understanding of the role technology plays in supporting individuals experiencing homelessness.