Product Owner

Who We Are

Chesapeake Employers’ Insurance Company is a purpose-driven organization dedicated to improving the lives and livelihoods of our policyholders, injured workers, team members, and the community. As a leading workers' compensation specialty insurer in the mid-Atlantic region, we take pride in being a force for good. Our 350 team members are committed to making a positive impact every day in the lives of all our stakeholders. Join our motivated, professional team as we foster a culture of values, teamwork, innovation, and collaboration. Established in 1914, Chesapeake Employers Insurance, headquartered in Towson, Maryland, has over a century of experience, a strong financial foundation, and an "A" rating from AM Best.

POSITION SUMMARY:
The Product Owner at Chesapeake is responsible for defining, prioritizing, and delivering product capabilities that drive customer outcomes, operational efficiency, and business value within an insurance and workers’ compensation environment.

Operating within Chesapeake’s cross-functional delivery model, this role manages intake and backlog prioritization, partners with leadership to align initiatives with business and financial objectives, and serves as a trusted liaison between business stakeholders, IT delivery teams, and vendors to clarify requirements, remove roadblocks, and deliver measurable outcomes.

The Product Owner applies strong business acumen, customer-centric thinking, and Agile best practices to support product adoption through change enablement, communication, training, and continuous improvement of product ways of working across Chesapeake.

DUTIES AND RESPONSIBILITIES:

• Manage intake, evaluation, and prioritization of product requests, partnering with operational leadership and cross-functional stakeholders to align initiatives with business strategy and customer needs.
• Own product adoption and change enablement, including planning, communication, and training coordination in partnership with Change Management and operational teams.
• Collaborate with leadership on product vision, roadmap, and prioritization decisions, balancing value, risk, and stakeholder priorities.
• Serve as the primary liaison between business stakeholders, project managers, vendors, and IT delivery teams, resolving ambiguity and removing delivery obstacles.
• Translate business problems, regulatory needs, and stakeholder input into user stories, acceptance criteria, and measurable outcomes.
• Maintain and prioritize the product backlog, leading refinement sessions to ensure readiness, clarity, and alignment.
• Partners with architects and engineering teams to evaluate solution options and deliver capabilities that support claims, underwriting, policy, finance, billing, or reporting workflows.
• Communicate clear, consistent product progress, risks, and outcomes to stakeholders.
• Support operational users through software guidance, issue resolution, and training, including classroom or one-on-one sessions as needed.
• Represent stakeholder interests in vendor engagements, including roadmap discussions, enhancements, and issue resolution.
• Participate in stakeholder forums, on-site visits, and industry events to understand user experience and market trends.
• Contribute to retrospectives and lessons learned to continuously improve product delivery and working practices.
• Contributes to the achievement of established department goals and objectives; adheres to departmental policies, procedures, quality, and safety standards, and consistently exhibits Chesapeake’s Values and Behaviors.
• Performs other duties as assigned.

SKILLS, EDUCATION AND EXPERIENCE:
Required

• Bachelor’s degree in Business, Information Systems, Finance, Insurance, or a related field.
• 3–5 years of experience in product ownership, business analysis, operations, or IT within insurance, workers’ compensation, financial services, or a regulated industry.
• Strong understanding of business operations and process flows.
• Proven customer-centric mindset with experience translating needs into product outcomes.
• Demonstrated ability to facilitate discussions, manage stakeholder expectations, and balance competing priorities.
• Strong analytical, problem-solving, and organizational skills.
• Ability to communicate complex concepts clearly to technical and non-technical audiences.
• Working knowledge of Agile/Scrum practices, including backlog management and value delivery.
• Understanding of the role of data in decision-making, compliance, and business value.

Preferred

• Experience with insurance, workers’ compensation, or financial services platforms.
• Agile and Product certifications are a plus:
• PSPO (Professional Scrum Product Owner)
• PSM (Professional Scrum Master)
• CSPO (Certified Scrum Product Owner)
• CSM (Certified ScrumMaster)

POSITIONAL COMPETENCIES:

• Bias for Action
• Knowledge Sharing
• Deliver Results
• Service and Sales Excellence
• Personal Leadership
• Teamwork and Communication

PHYSICAL DEMANDS:
While performing the duties of this job, the employee is regularly required to sit, use hands to finger, handle or feel objects, tools or controls; reach with hands and arms. The employee is occasionally required to stand, walk, stoop, kneel, crouch or crawl. The employee may occasionally lift up to 30 pounds. Specific vision abilities are required which include, close vision, peripheral vision and the ability to adjust focus.

WORK ENVIRONMENT:
Office Environment. The noise level is usually moderate.

SALARY
$93,057.00 - $144,238.00 (per year, commensurate with experience. Exempt.)

What We Offer

We offer a competitive benefits package that includes health, vision, and dental coverage, a robust PTO plan, an 8% employer contribution to retirement regardless of team member contribution, educational assistance, and opportunities to participate in team member appreciation events. Additionally, we provide STD, LTD and group life insurance 1X a team members salary. You'll also enjoy free tickets to community attractions, all part of our commitment to providing a high quality of work life. You will have the flexibility to thrive in a hybrid work environment and an opportunity to participate in development and volunteer programs.