AI Workforce Enablement Lead; Remote

Progressive Leasing is a leading provider of in-store and e-commerce lease‑to‑own solutions. With more than 20 years in Fin Tech, 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 Fin Tech 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.

PROG is dedicated to providing people with opportunity — opportunity for inclusive collaboration, opportunity for innovation, and opportunity for development.

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.

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.

• 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

• 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

• 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

Progressive Leasing welcomes and encourages diversity in the workplace. We do not discriminate in any aspect of employment on the basis of race, color, religion, national origin, ancestry, gender, sexual orientation, gender identity and/or expression, age, veteran status, disability, or any other characteristic protected by federal, state, or local employment discrimination laws where Progressive Leasing does business.