At Frontline Insurance, we are on a mission to Make Thing Better, and our Principal Product Owner plays a pivotal role in achieving this vision. We strive to provide high quality service and proactive solutions to all our customers to ensure that we are making things better for each one.

What makes us different? At Frontline Insurance, our core values – Integrity, Patriotism, Family, and Creativity – are at the heart of everything we do. We’re committed to making a difference and achieving remarkable things together. If you’re looking for a role, as a Principal Product Owner where you can make a meaningful impact and grow your career, your next adventure starts here!

Our Principal Product Owner enjoys robust benefits:

· Hybrid work schedule!

· Health & Wellness: Company-sponsored Medical, Dental, Vision, Life, and Disability Insurance (Short-Term and Long-Term).

· Financial Security: 401k Retirement Plan with a generous 9% match

· Work-Life Balance: Four weeks of PTO and Pet Insurance for your furry family members.

What you can expect as a Principal Product Owner:

Team Leadership and Product Owner Development: Lead, coach, mentor, and develop a team of Product Owners, including setting performance expectations, supporting development plans, conducting performance management activities, succession planning, and building team capability across Guidewire product domains.
Role Authority and Escalation: Provide day-to-day product leadership for the Product Owner team, escalate priority conflicts and delivery risks to PMO leadership and ensure product decisions align with approved roadmap priorities, governance standards, and enterprise objectives.
Guidewire Strategy and Delivery: Oversee execution of the enterprise roadmap and delivery of enhancements, upgrades, migrations, cloud transformation, digital modernization, and related integration initiatives across Guidewire applications and related capabilities, including PolicyCenter, BillingCenter, ClaimCenter, ContactManager, Digital Portals, and third-party integrations. This role reports directly to the Director of Guidewire Product Excellence and is responsible for guiding Product Owner activities that support project delivery based on the roadmap developed by PMO and Application Delivery leadership and approved by the executive team.
Product Governance and Agile Practices: Establish and continuously improve product ownership standards, product governance, prioritization methodologies, Agile practices, planning processes, and product management frameworks across the Product Owner team.
Backlog, Requirements, and Prioritization: Ensure Product Owners translate business workflows, strategic objectives, market opportunities, and regulatory changes into features, epics, user stories, acceptance criteria, product enhancements, and roadmap initiatives; maintain consistent backlog management and prioritize work based on business value, risk, regulatory requirements, and technical dependencies.
Stakeholder Engagement and Business Alignment: Build strong partnerships with underwriting, claims, billing, customer service, compliance, operations, business SMEs, delivery teams, Application Delivery leadership, and PMO leadership to facilitate prioritization, communicate product status, manage risks and dependencies, and drive consensus across business and technology stakeholders.
Insurance Product Expertise: Serve as a subject matter expert for Property & Casualty products, with emphasis on Homeowners, Dwelling Property, and Commercial Property insurance, ensuring product enhancements support regulatory requirements, policy, claim and billing lifecycle management, underwriting and claim guidelines, and business development requirements.
Metrics, Compliance, and Continuous Improvement: Monitor team performance, delivery outcomes, product KPIs, operational metrics, user feedback, business value realization, customer satisfaction measures, and lessons learned to identify improvement opportunities and promote a culture of innovation, customer-centricity, and operational excellence.

What we are looking for as a Principal Product Owner:

Required

Bachelor's degree in Business, Information Technology, Computer Science, or related field.
8+ years of experience in product management, business analysis, project delivery, or Agile leadership.
3+ years of leadership experience managing Product Owners, Business Analysts, or Agile teams.
Experience delivering solutions within the Property & Casualty insurance industry.
Strong knowledge of Guidewire applications and insurance business processes.
Experience working within Agile and SAFe delivery environments.
Proven ability to manage multiple priorities in a complex enterprise environment.
Demonstrated experience leading enterprise-scale product portfolios and transformation initiatives.
Strong understanding of Agile methodologies, Scrum principles, and product management frameworks.
Exceptional communication, facilitation, negotiation, and executive presentation skills.

Insurance Experience

10+ years of multi-state Property & Casualty insurance experience, with significant expertise in Homeowners, Commercial Property, Underwriting, Policy Administration, Billing, Claims, and Regulatory Compliance.
Experience supporting insurance modernization and business transformation initiatives.

Guidewire Experience

5+ years of Guidewire experience across On-Prem environments – strongly preferred
2+ years of Guidewire experience across Cloud environments – strongly preferred
Strong knowledge of PolicyCenter, BillingCenter, ClaimCenter, ContactManager and associated Guidewire On-Prem and Cloud capabilities.

CERTIFICATES, LICENSES, REGISTRATIONS (Preferred)

Guidewire Certified Professional (Cloud and/or InsuranceSuite)
Professional Scrum Product Owner (PSPO)
SAFe Product Manager/Product Owner (SAFe PMPO)
Associate in General Insurance (AINS)
Chartered Property Casualty Underwriter (CPCU) — strongly preferred

Why work for Frontline Insurance?

At Frontline Insurance, we’re more than just a workplace – we’re a community of innovators, problem solvers, and dedicated professionals committed to our core values: Integrity, Patriotism, Family, and Creativity. We provide a collaborative, inclusive, and growth-oriented work environment where every team member can thrive.

Frontline Insurance is an equal-opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.

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