Senior/Lead Product Strategist – Castle

Senior/Lead Product Strategist – Castle

Job Number: 186141

Level20 is the new business incubator for Progressive. We are built on the principle that people face real problems every day and deserve real solutions. By addressing unmet needs, we provoke growth beyond insurance to develop new ideas, products, and services that help people overcome, succeed, and thrive. At Level20, we operate with the speed and agility of a start-up, empowered by Progressive’s scale and resources. Learn more about our vision and team at

As a senior/lead product strategist at Level20, you’ll work on Castle, a human-first, digitally enabled home service concierge experience (learn more at Castle envisions a world where every homeowner is empowered with easy access to the knowledge, insight, and resources needed to effortlessly address any home repair need. You’ll be responsible for driving the research, design, development, and commercialization of new product features supporting a two-sided home repair marketplace. You’ll be part of a cross-functional team leveraging iterative product design to grow and scale the Castle business. In addition, you’ll wear many hats, and embrace a fast-acting, cross-disciplinary approach to work.

Location: Cleveland, Ohio.

Must-have qualifications

  • Bachelor’s degree or higher
  • Minimum of three years of professional work experience defining and creating user insight driven digital products or services

Preferred skills

  • Demonstrated ability to partner closely with engineering, design, and business operations to identify opportunities, test hypotheses, and lead iterative concept testing for new features and products.
  • Product owner/scrum process experience, bringing new digital-first products to market through identifying user needs and interests, development of product positioning, defined feature requirements, and creation of a prioritized product/feature roadmap(s). Experience supporting a two-sided marketplace is a plus.
  • Experience working with Agile development teams and expertise in the product development lifecycle, leading highly cross-functional groups, demonstrating mastery of planning and prioritization in a fast-paced development cycle.
  • Proven application of qualitative and quantitative data to make business decisions, measure outcomes, and drive execution to deliver meaningful impact and growth.
  • Entrepreneurial, experimental, data-driven product leader with a passion for testing and developing new products in an ambiguous environment with a very large problem space.


$80,300 – $131,500/year depending on position level and experience
Gainshare bonus up to 30% – 40% (depending on position level) of your eligible earnings based on company performance


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
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

Equal Opportunity Employer