AI Workforce Enablement Lead | People Team (Remote)

Progressive Leasing

$110K — $130K *
US-AnywhereRemote in Arizona, US
Business Services
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of experience in workforce transformation or talent-side change execution
  • Proven track record of driving behavior change, not just training
  • Experience with HR/Talent systems like role design and performance
  • Strong judgment and autonomy in fast-paced environments
  • Ability to assess resistance and tailor support
  • Curious about AI-enabled work processes
  • Bachelor's degree or equivalent work experience

Responsibilities

  • Own the workforce enablement strategy for AI-related changes
  • Design and implement impactful enablement programs
  • Support managers in leading teams through transitions
  • Translate workflow changes into clear role expectations and skills
  • Create practical toolkits and resources for managers
  • Collaborate with HR, Talent, and AI teams for proactive enablement
  • Monitor adoption through leading indicators and refine strategies accordingly

Benefits

  • Full Health Benefits including Medical, Dental, Vision, and Life Insurance
  • Paid Parental Leave
  • Company-Matched 401(k) Plan
  • Paid Time Off, Holidays, and Volunteer Hours
  • Employee Resource Groups for diverse communities
  • Employee Stock Purchase Program
  • Tuition Reimbursement
  • Charitable Gift Matching
  • Provision of job-required equipment and services
Full Job Description
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.

YOU ARE: 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


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