AI Workforce Enablement Lead | People Team (Remote)
About The Position
Progressive Leasing is seeking an AI Workforce Enablement Lead to support its enterprise AI transformation. This role will ensure employees are equipped to succeed as work evolves due to AI integration. The position is a remote, work-from-home role that can be performed anywhere in the continental US. The People team at PROG is a lean, embedded team focused on enabling employees and managers to adopt new ways of working in a practical, supported, and sustainable manner. This involves partnering with Talent, HR, and Technology to redesign work and guide the workforce through these changes with clarity and confidence. The ideal candidate is a hands-on leader experienced in turning transformation goals into real behavior change, designing systems, manager support, and enablement for employee transitions. This is an individual contributor role offering significant responsibility, autonomy, and impact.
Requirements
- 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
Responsibilities
- Own the workforce enablement approach for AI-driven workflow and role changes
- Design and run enablement programs that drive real adoption
- 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)
- Continuously refine approaches based on real signals from employees and managers
Benefits
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Senior
