AI Workforce Enablement Lead | People Team (Remote)
Progressive Leasing · Arizona, United States
- On site
- Full-time
- $120,000 / year
- Arizona, United States
Job highlights
- Lead AI workforce transformation efforts.
- Drive real employee adoption of new workflows.
- Equip managers to support team transitions.
- Design practical enablement tools and resources.
- Individual contributor role with high impact.
About the role
About Progressive Leasing
Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. With more than 20 years in FinTech, we’ve grown from start-up to industry leader by innovating, simplifying, and valuing people. We are a subsidiary of PROG Holdings (NYSE: PRG), a FinTech holding company with three business segments: Progressive Leasing, Purchasing Power (a leading employee purchase program for consumer products and services using payroll deduction), and Four, a Buy Now Pay Later (BNPL) platform.
We are currently hiring an AI Workforce Enablement Lead to help support our enterprise AI transformation and ensure our people are set up to succeed as how work gets done evolves.
This role is a work‑from‑home position and can be performed remotely anywhere in the continental US.
Employee Value Proposition (EVP)
PROG is dedicated to providing people with opportunity — opportunity for inclusive collaboration, opportunity for innovation, and opportunity for development.
WE ARE: The People Team
The People team at PROG is lean, highly embedded with the business, and operating at the center of a company‑wide shift to AI‑enabled work. As workflows change, our focus is not just on tools — but on ensuring employees and managers actually adopt new ways of working in a practical, supported, and sustainable way.
We partner closely across Talent, HR, and Technology to redesign work thoughtfully and enable our workforce to move forward with clarity and confidence.
YOU ARE: A Leader in Workforce Enablement
A hands‑on workforce enablement and change execution leader who knows how to turn big transformation goals into real behavior change.
You’re not just building training or communications — you’re designing the systems, manager support, and enablement that help employees successfully transition as roles and workflows evolve. You’re comfortable operating with ambiguity, partnering closely with the business, and owning outcomes end‑to‑end.
This is an individual contributor role with real responsibility, autonomy, and impact.
Your Day-to-day
- Own the workforce enablement approach for AI‑driven workflow and role changes
- Design and run enablement programs that drive real adoption — not “check‑the‑box” training
- Equip managers to lead teams through transition, including readiness, support, and tough conversations
- Translate redesigned workflows into clear role expectations, skills, and enablement plans
- Build practical toolkits, learning experiences, and manager resources that actually get used
- Partner across Talent, HR, and AI teams to ensure enablement comes before accountability shifts
- Track adoption using leading indicators (behavior change, readiness, friction), not vanity metrics
- Continuously refine approaches based on real signals from employees and managers
You’ll Bring
- 5+ years of experience in workforce transformation, people enablement, or talent‑side change execution
- Proven experience driving behavior change — not just delivering training or communications
- Comfort working inside or closely with HR/Talent systems (role design, skills, learning, performance)
- Strong judgment, autonomy, and follow‑through in fast‑moving environments
- Ability to diagnose resistance and tailor support appropriately
- Practical curiosity and experience with AI‑enabled ways of working (you don’t need to be an engineer)
- Bachelor’s degree or equivalent work experience
AI‑enabled tools are already part of how work gets done at PROG, and their use will continue to expand. We value people who are curious, adaptable, and open to learning as roles and workflows evolve.
We Offer
- Competitive Compensation
- Full Health Benefits; Medical/Dental/Vision/Life Insurance + Paid Parental Leave
- Company‑Matched 401(k)
- Paid Time Off + Paid Holidays + Paid Volunteer Hours
- Employee Resource Groups (Black Inclusion Group, Women in Leadership, PRIDE, Adelante)
- Employee Stock Purchase Program
- Tuition Reimbursement
- Charitable Gift Matching
- Job‑required equipment and services
Key skills/competency
- AI Workforce Enablement
- People Team Transformation
- Change Execution
- Talent Management
- Employee Enablement
- HR Systems Integration
- Behavioral Change
- AI Workflow Design
- Manager Enablement
- Remote Work
Skills & topics
- AI Workforce Enablement
- People Team
- Change Management
- Talent Development
- HR Transformation
- Remote Work
- Employee Enablement
- FinTech
- Workforce Transformation
- AI Adoption
How to get hired
- Tailor your resume: Highlight 5+ years in workforce transformation, change execution, and HR systems. Quantify achievements in driving behavior change and enabling teams through AI adoption.
- Showcase AI familiarity: Emphasize practical curiosity and any experience with AI-enabled work, even non-technical. Detail your ability to diagnose resistance and tailor support.
- Address remote work: Confirm your ability to work autonomously and effectively in a remote, continental US setting. Mention experience operating with ambiguity.
- Prepare for behavioral questions: Be ready to discuss specific examples of leading change, equipping managers, and measuring adoption through leading indicators.
Technical preparation
Behavioral questions
Frequently asked questions
- What is the AI Workforce Enablement Lead role at Progressive Leasing?
- The AI Workforce Enablement Lead at Progressive Leasing is an individual contributor role focused on supporting the company's enterprise AI transformation. This position drives the adoption of AI-enabled workflows and role changes by designing and implementing enablement programs, equipping managers, and creating practical resources for employees. The goal is to ensure the workforce successfully transitions to new ways of working.
- Can I work remotely for the AI Workforce Enablement Lead position at Progressive Leasing?
- Yes, the AI Workforce Enablement Lead position at Progressive Leasing is a work-from-home role. It can be performed remotely from anywhere within the continental United States. Progressive Leasing values flexibility and supports remote work arrangements for this position.
- What experience is required for the AI Workforce Enablement Lead role?
- The AI Workforce Enablement Lead role requires at least 5 years of experience in workforce transformation, people enablement, or talent-side change execution. Proven experience in driving behavior change, comfort with HR/Talent systems (role design, skills, learning, performance), strong judgment, and practical curiosity with AI-enabled ways of working are also essential. A Bachelor's degree or equivalent work experience is needed.
- How does Progressive Leasing support employee development in this role?
- Progressive Leasing offers a comprehensive Employee Value Proposition focused on opportunity. For the AI Workforce Enablement Lead, this includes opportunities for inclusive collaboration, innovation, and development. The company provides competitive compensation, full health benefits, 401(k) matching, PTO, and tuition reimbursement, supporting continuous learning and growth.
- What is the company culture like at Progressive Leasing for this role?
- The People team at Progressive Leasing is described as lean, highly embedded with the business, and central to the company's AI transformation. The culture emphasizes practical, supported, and sustainable adoption of new ways of working. They partner closely across departments to enable the workforce with clarity and confidence, fostering an environment of curiosity and adaptability.
- How are enablement programs measured at Progressive Leasing?
- Progressive Leasing emphasizes tracking adoption using leading indicators rather than vanity metrics. This includes monitoring behavior change, readiness, and friction points. The AI Workforce Enablement Lead is expected to continuously refine approaches based on real signals from employees and managers.