The Progressive Corporation

AI Workforce Enablement Lead | People Team (Remote)

The Progressive Corporation$90K — $130K *
US-AnywhereRemote in Arizona, US
Business Services
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years in workforce transformation or people enablement
  • Experience driving behavior change beyond training
  • Familiarity with HR/Talent systems
  • Strong judgment and autonomy in fast-paced settings
  • Ability to assess resistance to change
  • Curiosity about AI-enabled work practices
  • Bachelor's degree or equivalent experience

Responsibilities

  • Own workforce enablement for AI-driven changes
  • Design impactful enablement programs
  • Support managers in leading teams through transition
  • Translate workflows into clear role expectations
  • Create practical toolkits and resources for managers
  • Collaborate with HR and AI teams on enablement
  • Track adoption using measurable indicators
  • Refine strategies based on feedback from employees

Benefits

  • Full health benefits including medical, dental, vision, and life insurance
  • Company-matched 401(k) plan
  • Paid time off and paid holidays
  • Opportunities for volunteer work during paid hours
  • Employee resource groups for diversity and inclusion
  • Employee stock purchase program
  • Tuition reimbursement for educational advancement
  • Charitable gift matching
  • 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.

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


About The Progressive Corporation

Progressive is a place where innovation and collaboration are a way of life. Each of our employees has a role in our success and together, we continue to find new and better ways to satisfy our customers and move the insurance industry forward.

The Progressive Corporation Careers

Join the vibrant team at The Progressive Corporation, a leader in the insurance industry, and propel your career to new heights with a company known for innovation, leadership, and a commitment to diversity and growth.

Work You’ll Do

At The Progressive Corporation, we offer more than just job opportunities; we provide a platform for professional development and personal growth. As part of our team, you will contribute to transformative projects that redefine the standards of the insurance industry. Our collaborative culture ensures that every team member has the opportunity to make a significant impact.

Empower Your Career

Step into a role that challenges and excites you. At Progressive, you can navigate through a variety of career paths with the support of our extensive training and development programs. From leadership training to diversity workshops, we equip our professionals with the tools they need to excel.

Innovate with Us

Join a group of forward-thinkers who are constantly driving innovation in the insurance sector. At Progressive, your skills in technology, industry expertise, and digital innovation will help shape solutions that meet the evolving needs of our customers.

Internship Programs

Kickstart your career with The Progressive Corporation’s internship programs. Gain invaluable experience, build your resume, and develop professional networking connections that will benefit your career for years to come. Our internships offer a deep dive into the insurance industry, providing a robust foundation for future success.

Benefits and Culture

Choose a career with The Progressive Corporation and enjoy a wealth of benefits that go beyond the basics. Our inclusive culture supports our employees’ life stages and fosters a workplace where everyone can thrive. Health, wellness, financial planning, and work-life balance are just the beginning of what we offer.

Join Our Team

Explore the numerous positions available at Progressive, from entry-level to executive, and find where your expertise can make the most impact. We are continuously hiring talented individuals who are passionate about making a difference and ready to contribute to our culture of continuous improvement.

Stay Connected

Keep up to date with the latest at Progressive: - **Career Insights**: Get insider perspectives and industry-leading insights through our careers blog. - **Job Alert Emails**: Customize your subscription to receive job alerts and news tailored to your preferences. Discover the exciting and rewarding opportunities that await at The Progressive Corporation.

Explore Job Opportunities

Search open positions that match your skills and interests. We look for curious, creative, and solution-driven team players who are eager to drive progress and thrive in a dynamic environment.

SEARCH PROGRESSIVE JOBS

At The Progressive Corporation, your career is what you make of it. Grow, innovate, and lead with us as we redefine the future of insurance. Join us and be part of a team that values diversity, innovation, and the professional growth of its members.
Learn more about The Progressive Corporation
Size
49,000 employees
Market Cap
$75.6 billion
Industry
Net Income
$5.7 billion
Founded
1937
5 Year Trend
+15.3%
Revenue
$42.6 billion
NASDAQ

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