Agile Delivery Owner Lead- Progressive Life

As an Agile Delivery Owner Lead, you’ll play a critical role in enabling our product teams to deliver high‑quality, customer‑focused solutions that advance Progressive Life’s digital strategy. In this role, you’ll provide day‑to‑day leadership of agile practices, fostering clarity, alignment, and continuous improvement across the team. As a trusted partner to Product, Engineering, and Business stakeholders, you’ll ensure that work flows smoothly, from shaping clear requirements to driving predictable delivery and elevating team performance over time. Utilizing a servant leadership approach, you’ll help establish structured delivery discipline across multiple teams, remove barriers proactively, and help teams navigate ambiguity with confidence.

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 a pivotal moment as we advance our transition to Agile delivery, leading the adoption and execution of Scrum practices across teams.

This is a hybrid role based in Cleveland, Ohio. We value inclusive collaboration and work in-person Tuesday through Thursday at the Level20 downtown office (800 W St Clair Ave STE 200, Cleveland, OH 44113) with free parking. We will be relocating to the Progressive headquarters campus (300 North Commons Blvd, Mayfield Village, Ohio 44143) later this year.

Must-have qualifications

• A minimum of 7 years of experience as an Agile Delivery Owner, Scrum Master, Project Manager, or an equivalent leadership role for development team member using scrum, kanban, or other industry standard agile practices.
• {OR} Bachelor's Degree or higher in an Information Technology or Business-related discipline or related field of study (e.g., Computer Science, Software Engineering, MIS, Business Management) and a minimum of 4 years of experience as an Agile Delivery Owner, Scrum Master, Project Manager or an equivalent leadership role for a development team using kanban, scrum, or other industry standard agile practices.
• Certified Advanced ScrumMaster and/or Professional Scrum Master II, plus Agile Leadership Certification required in addition to the above education and/or experience.

Preferred skills

• Deep understanding of Agile frameworks (Scrum, Kanban) and the ability to tailor them thoughtfully to team needs
• Strong capability in enabling teams to refine requirements with clarity (e.g., well‑formed acceptance criteria, ready‑for‑dev standards)
• Experience improving team delivery predictability through data, metrics, and transparent workflow management and familiarity with Jira or similar tools for backlog management, workflow visibility, and reporting.
• Proven ability to partner with Product, Engineering, and Business stakeholders to align on priorities and outcomes, while navigating ambiguity, facilitating decisions, and fostering accountability across diverse roles and perspectives
• Exceptional communication and servant leadership skills, including synthesizing complex topics, engaging teams around shared goals, conflict resolution, empowering teams, building trust, and creating an environment where people can do their best work

Compensation

• $118,000-$131,000/year depending on experience
• Gainshare bonus 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 2025 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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