Progressive

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As a senior product strategist with Progressive Life, you’ll lead product strategy and roadmap development for key areas of our growing direct-to-consumer life insurance business. In this role, you’ll connect business goals and customer needs to product opportunities, lead discovery, and prioritize solutions that support continued growth. You’ll partner across business, technology, legal, compliance, and other teams to influence decisions, maintain transparency around priorities and progress, and help strengthen how product strategy is governed and executed. As the organization continues to grow, you’ll play a key role in shaping new products and capabilities and helping Progressive Life scale with greater structure and discipline.

Progressive Life began within Level20, Progressive’s growth incubator, where we built a term life insurance product and business from the ground up. After a successful launch and early growth, we’ve spun out into the Strategy group, now focused on scaling our products, capabilities, and impact. You’ll be joining the organization at an exciting stage of growth as the team continues to build and expand products, capabilities, and delivery practices.

This is a hybrid role based in Cleveland, Ohio. We value inclusive collaboration and work in-person on Tuesdays and Wednesdays at our headquarters, 300 N Commons Blvd., Mayfield Village, OH 44143. Work-from-home days are possible for this position on Mondays, Thursdays, and Fridays.

Minimum qualifications

• A minimum of 7 years professional work experience managing the definition and delivery of digital products and services
• {OR} Bachelor's degree or higher and a minimum of 4 years of professional work experience managing the definition and delivery of digital products or services

Preferred skills

• Demonstrated ownership of meaningful parts of the digital customer journey, with a strong understanding of customer behavior, product performance, and conversion metrics to inform product decisions
• Experience working with regulated products or within a regulated industry, with an understanding of how compliance and governance considerations can impact product decisions
• Project management experience supporting large or complex product initiatives, including coordinating dependencies, timelines, and stakeholder needs
• Experience with product governance frameworks and structured decision-making approaches, including stage-gate methodology
• Strong collaboration and influencing skills, with the ability to build alignment, navigate competing priorities, and drive direction across cross-functional teams; comfortable with ambiguity and evolving business needs

Compensation

• $120,000 - $150,000/year 
• Gainshare annual cash incentive payment up to 30% of your eligible earnings based on company performance

Benefits

• 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.

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