AI Workforce Enablement Lead (Remote)

Progressive Leasing

3d • Remote

About The Position

Progressive Leasing is seeking an AI Workforce Enablement Lead to support its enterprise AI transformation. This role will ensure employees and managers are equipped to succeed as work evolves due to AI integration. The People team at PROG is a lean, embedded group focused on driving practical, supported, and sustainable adoption of new AI-enabled ways of working. This individual contributor role offers 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 (engineering expertise not required).
• 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 difficult conversations.
• Translate redesigned workflows into clear role expectations, skills, and enablement plans.
• Build practical toolkits, learning experiences, and manager resources that are actively used.
• Partner across Talent, HR, and AI teams to ensure enablement precedes accountability shifts.
• Track adoption using leading indicators (behavior change, readiness, friction), not vanity metrics.
• Continuously refine approaches based on feedback 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: Associate degree
• Number of Employees: 501-1,000 employees