Contract Ai Strategy Jobs (NOW HIRING)

Position:  Director of AI Strategy & Enablement
Department:  Information Technology
Reports to:  VP of IT, Strategy and Innovation
Status:  Exempt

Goodwill Keystone Area is committed to creating a culture of belonging where all people feel respected and valued. This is because we celebrate the diversity of thought, the richness of the human experience and the desire to reflect the communities we serve.

Summary
The Director of AI Strategy & Enablement leads the design, governance, and enterprise-wide adoption of Goodwill Keystone Area's artificial intelligence strategy. This role is a strategic investment in our mission, focused on creating new opportunities for workforce development, leveraging AI to enhance operational efficiency, and amplifying fundraising efforts. In addition, the position manages AI initiatives from opportunity assessment through deployment, leads workforce enablement efforts, and establishes governance and best practices to support responsible, scalable use of AI and automation.

Duties and Responsibilities
AI Strategy & Roadmap

• Develop and own a sustainable, measurable enterprise AI strategy aligned to Goodwill Keystone's mission, with distinct plans for Retail/Donated Goods, Mission Services, and Business Services.
• Maintain a prioritized, resourced AI roadmap; lead the annual AI planning cycle with executive leadership.
• Frame problems, shape business cases, and define success metrics for each initiative before implementation begins.
• Monitor the external AI landscape – technologies, regulations, peer Goodwill affiliates, and nonprofit sector practice – and translate what matters into Goodwill Keystone's strategy.

AI Literacy & Workforce Enablement

• Drive the expansion of AI Forge – Goodwill Keystone's existing AI literacy program – to build a sustainable and enablement enterprise-wide model that focuses on: audience segmentation, role-based learning paths, progression levels, and measurement of adoption and capability growth.
• Establish a community of practice for AI champions across Retail, Mission Services, and Business Services to accelerate peer learning and local application.
• Oversee selection and management of external training partners, platforms, manages higher level AI projects and content providers that complement the AI Forge.

Project Management & Operational Implementation

• Work to identify, assist with prototype, and implement AI-powered solutions to improve efficiency in core business areas that deliver clear measurable impacts (KPIs). 
• Document current-state business processes and define future-state workflows as part of AI project scoping and implementation. 
• Oversee management of AI initiatives to ensure timely testing, establishes benchmarks (KPIs) for and perform ROI assessments, leads teams’ go-no go decisions (fail fast), and oversees the implementation and roll out. 
• Ensure end users are actively involved in project and provided training to use new tools. 
• Act as lead project manager on any grant projects that advance the use of new technologies.

Governance, Risk & Responsible AI

• Establish and maintain AI governance policies covering data protection, privacy, bias monitoring, human oversight, vendor review, and acceptable use.
• Chair or convene an AI Review function (cross-functional) to vet new AI use cases, tools, and vendor engagements.
• Ensure compliance with applicable regulations, funder requirements, and the data-handling obligations of state and federal contracts in Business Services.

Portfolio, Vendor Oversight & Enterprise Change

• Serve as Goodwill Keystone's primary relationship owner for external AI development partners and technology vendors.
• Assists in vendor selection, contracting, and accountability to scope, timeline, and measurable outcomes.
• Cultivate academic and nonprofit-sector partnerships to access talent, research, and shared practice.
• Represent Goodwill Keystone selectively at industry and nonprofit forums when doing so advances the strategy; external thought leadership is a supporting activity.

• Promotes an environment of workplace safety. Ensures that duties are performed in a safe manner and safety requirements are adhered to.
• Communicates progress, problems, and concerns to the VP of IT, Strategy and Innovation.
   

Education and Experience

• Bachelor’s required; Equivalent professional experience will be considered.
• Five (5) years prior experience in business process automation, workflow optimization, or solution development.
• Demonstrate experience developing and executing an AI strategy and base AI tools knowledge.
• Experience designing or leading workforce enablement, learning, or change management programs, ideally involving AI, data, or digital skills.
• Experience in project management.
• Experience establishing governance, policy, or risk frameworks for technology, data, or AI.
• Experience managing external vendors, consultants, or agency partners to delivery outcomes.
• Experience working in, with, or alongside mission-driven, nonprofit, or social-impact organizations strongly preferred.

Skills/Abilities/Qualifications

• Strong working understanding of the current AI landscape – generative AI, applied machine learning, automation, and responsible AI practice – sufficient to shape strategy, evaluate vendors, and guide internal decisions. Deep hands-on engineering skills are not required.
• Understanding of data protection, privacy, and ethical considerations for AI, including bias and human-in-the-loop design.
• Exceptional written and verbal communication; able to translate complex AI concepts into plain language for boards, executives, frontline staff, and community audiences.
• Strong critical thinking, problem-solving, and project management skills are essential for managing multiple initiatives simultaneously.  
• Structured strategic thinking; can define priorities, frame trade-offs, and say no to work that is out of scope.
• Comfort designing and facilitating working sessions with senior leaders and organization staff.
• Comfort teaching, coaching, and building literacy in others, from executives to frontline staff.
• Comfort representing Goodwill Keystone in public forums.
• Ability to effectively work as part of a team or independently.  
• Must have a modern reliable cell phone (Android or iOS).  
• Must possess a valid driver’s license and reliable vehicle or reliable transportation. 
• Ability to travel within Goodwill Keystone Area territory.

Goodwill Keystone Area is an Equal Opportunity Employer and is committed to complying with all federal, state, and local laws that prohibit discrimination in employment. We provide equal employment opportunities to all qualified individuals without regard to disability or status as a protected veteran.