Who We Are.
At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client’s unique needs, ensuring they feel confident and supported in every decision.
As both a franchise platform and direct insurance provider, We Insure empowers like-minded entrepreneurs with the opportunity to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results.
What sets us apart? We’re data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We're building something meaningful and looking for purpose-driven individuals to help lead the way.
Your Impact.
We Insure is seeking a Senior Product Manager to join our founding product team and help shape the technology platform for the agency of the future. We are building a small, high-impact product and engineering organization focused on creating connected, intuitive, and AI-enabled experiences for our agents, sales teams, service teams, and customers.
We sit at the intersection of customers, independent agents, franchise owners, carriers, and insurance technology providers. That position creates a broad set of product opportunities across customer acquisition, agent productivity, carrier connectivity, sales and service workflows, data, and back-office operations. You will identify the highest-value problems, determine the right combination of product development, configuration, partnership, and integration, and own solutions from discovery through adoption and measurable business impact.
This is a senior, high-autonomy role for someone who has built insurance technology before. We are looking for a product manager who understands broker and agency technology, carrier connectivity, and the realities of P&C distribution well enough to have informed opinions on day one. The right person has shipped high-quality software that users genuinely value and treats adoption and business results as personally owned outcomes.
We are also an AI-native product team. Every member of the team is expected to use AI tools daily, not occasionally, to draft requirements, synthesize research, analyze data, prototype ideas, and pressure-test their own thinking.
This position is open to remote candidates. The role requires occasional travel (up to approximately 20%) to our Chicago or Austin office locations to support business needs.
Key Responsibilities.
This role is centered on four areas of responsibility.
Insurance Technology & Agency Workflows
- Product Ownership: Lead discovery, scoping, sequencing, delivery, launch, and iteration for products that improve how our agents and operators acquire, advise, sell, and serve customers.
- Workflow Understanding: Map how work gets done across agency sales, service, carrier, and back-office processes, then identify the friction, re-entry, delays, errors, and missed opportunities worth solving.
- Platform & Ecosystem Decisions: Evaluate when We Insure should configure, integrate, partner, or build, and bring clear, evidence-backed recommendations that account for user value, economics, speed, and long-term flexibility.
- Carrier & Partner Connectivity: Partner with Carrier Relations, engineering, and external technology providers on APIs, data exchange, third-party data, workflow integration, and the practical realities of P&C underwriting and distribution.
- AI-Enabled Experiences: Identify practical ways to use AI and automation to reduce administrative work, improve decisions, and create better experiences for agents, operators, and customers.
- Incremental Delivery: Ship in focused slices, put useful workflows in users' hands early, and use what you learn to reshape the plan.
- Business Outcomes: Define and improve the operating, adoption, customer, and financial metrics that matter for each product area.
Product Strategy & Discovery
- Roadmap Ownership: Set and defend the roadmap for your product area with a clearly articulated thesis for sequencing.
- User Research: Run research and interviews directly with agents, CSRs, operators, and internal stakeholders, including shadowing them in their day-to-day work.
- Feedback System of Record: Maintain an AI-queryable source of truth for customer and stakeholder feedback so the team can interrogate the corpus instead of repeatedly rereading it.
- Market Awareness: Track broker technology, insurtech, carrier connectivity, and emerging AI capabilities, and translate relevant developments into product decisions.
- Requirements: Write crisp PRDs, user stories, acceptance criteria, and specifications that engineers can build from without guesswork.
- Sprint Partnership: Work with engineering through the full delivery cycle: clarifying requirements, triaging questions, validating builds, and unblocking the team.
- Release Readiness: Own QA coordination, data migration, training materials, rollout sequencing, stakeholder communication, and post-launch support.
- Risk & Dependency Management: Track dependencies, risks, and open decisions transparently so no one is surprised.
Measurement & Cross-Functional Leadership
- Success Metrics: Define metrics before launch, instrument the product to capture them, and build the dashboards and reporting needed to track them.
- Analysis: Pull and analyze product, operational, and business data to determine whether something is working, for whom, and why.
- Impact Reviews: Lead post-launch reviews covering what shipped, what changed, what the team learned, and what comes next.
- Stakeholder Partnership: Serve as the trusted product partner across the business and communicate clearly with audiences ranging from engineers to senior leadership.
- Cross-Functional Leadership: Partner closely with the Head of Technology, Senior Full Stack Engineers, and stakeholders across Sales, Account Management, Carrier Relations, Service, and FinOps.
Qualifications
Required Qualifications
- Bachelor's degree in Business, Computer Science, Information Systems, or a related field, or equivalent professional experience.
- 5+ years of product management experience, or equivalent ownership of technology products from discovery through launch and continuous improvement.
- Minimum 3 years of experience in the property and casualty insurance industry. 5+ years is strongly preferred.
- Experience building broker or agency technology, either within an agency or brokerage or on the carrier or technology-provider side serving independent agents.
- Strong knowledge of the P&C insurance ecosystem, including carriers, MGAs, wholesalers, agencies, the policy lifecycle, lines of business, underwriting, and commission structures.
- Experience with insurance distribution technology such as agency management systems, CRM and workflow platforms, quoting and rating solutions, carrier portals, carrier APIs, and third-party data providers.
- Proven success delivering high-quality digital products with a strong focus on user experience and adoption.
- Demonstrated ability to own product outcomes from strategy through execution and measure success based on business results.
- Strong analytical skills and experience using SQL, spreadsheets, and analytics tools to make data-driven decisions.
- Technical understanding of APIs, integrations, data models, and automation, with the ability to partner effectively with engineering teams without writing production code.
- Experience delivering complex, integration-heavy software products in collaboration with cross-functional teams.
- Strong written and verbal communication skills, with the ability to influence stakeholders across technical and nontechnical teams.
- Comfort working in a fast-paced, evolving environment with ambiguity and changing priorities.
- Demonstrated proficiency using AI tools to improve productivity, research, problem-solving, and product development.
Preferred Qualifications
- Deep experience with quoting, comparative rating, carrier connectivity, policy administration, or agent-facing workflow products.
- Experience working within a franchise, MGA, or distributed agency model.
- Experience building AI-powered prototypes, automations, or internal tools.
- Demonstrated experience designing customer-centric products that simplify complex workflows.
Our Values. The We Way.
At We Insure, Group our values shape how we work, how we lead, and how we grow together. They’re more than just words, they guide every interaction, every decision, and every customer experience.
We Way Reflects Our Commitment to.
- We personalize protection at a price you can trust
- We hustle to find opportunity
- We have fun along the way
- And—we’re just getting started
