Business Leader AI Transform & Value

Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun.

As the business leader for AI transformation & value realization, you’ll ensure enterprise artificial intelligence initiatives deliver measurable business outcomes and are adopted into day‑to‑day workflows. You’ll lead a focused portfolio of enterprise AI transformations from concept through implementation, adoption, measurement, and value realization. You’ll report to the Chief AI Officer and partner with business areas, technology, data, operations, HR, finance, legal, risk/compliance, security, and other stakeholders to align teams around shared outcomes and remove barriers.

You’ll embed AI‑enabled changes into business processes and identify and scale repeatable transformation approaches across processes, teams, and business areas. You’ll work across organizational boundaries and be accountable for driving execution, adoption, benefits realization, and sustained business outcomes from enterprise AI initiatives. These include productivity, efficiency, quality, growth, customer experience, workforce, and risk outcomes.

Location: Remote

• A minimum of 12 years of experience in business transformation, process improvement, product/program leadership, operations, technology‑enabled change, AI, analytics, or strategic execution, with at least 6 years of leadership experience.
• {OR} Bachelor's degree or higher in business, technology, data science, analytics, finance, operations, industrial engineering, or a related field of study and a minimum of 9 years of experience in business transformation, process improvement, product/program leadership, operations, technology‑enabled change, AI, analytics, or strategic execution, with at least 6 years of leadership experience.

• Experienced senior transformation leader with a track record of delivering measurable business outcomes.
• Strong cross‐functional leadership and influence skills.
• Experience leading large‑scale operating, digital, technology, or AI‑enabled transformations.
• Experience focused on adoption, execution, and outcomes rather than strategy alone.
• Comfortable driving change across organizational boundaries, often without formal authority.

• Base $208,620 - $254,980/year
• Gainshare annual cash incentive payment up to 75% of your eligible earnings based on company performance
• Participation in our restricted stock unit plan

• 401(k) with dollar‑for‑dollar company match up to 6%
• Medical, dental & vision, including free preventative care
• Wellness & mental health programs
• Health care flexible spending accounts, health savings accounts, & life insurance
• Paid time off, including volunteer time off
• Paid & unpaid sick leave where applicable, as well as short & long‑term disability
• Parental & family leave; military leave & pay
• Diverse, inclusive & welcoming culture with Employee Resource Groups
• Career development & tuition assistance
• Onsite gym & healthcare at large locations

Energage recognizes Progressive as a 2026 Top Workplace for:
Innovation, Purposes & Values, Work‑Life Flexibility, Compensation & Benefits, and Leadership.

Equal Opportunity Employer

Applicants must be authorized to work for any employer in the U.S. without the need or potential need, of current or future sponsorship for employment. Progressive does not hire candidates with (e.g., F-1 CPT, OPT, or STEM OPT, H-1B, O-1, E-3, TN) statuses for this role.

We’ll consider qualified applicants with arrest and conviction records. Note that federal law may prohibit individuals with certain felony convictions from working in the insurance industry unless they have obtained the required regulatory authorization.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.