Director of Product Manager

Warner Pacific Insurance Services is one of the nation’s largest privately held general agencies, connecting brokers, employers, and carriers across health and ancillary benefits. We sit at the center of a complex value chain — and we are investing heavily in the platforms, data, and automation that make that chain work better for everyone on it.

About the role

We’re hiring a Director of Product Management to own our Post-sale capabilities, with a mandate to fundamentally modernize the enrollment experience for our brokers, employer clients, and their employees. Post-sale is where our client relationship is either earned or eroded. Today, enrollment is where the most friction, manual effort, and downstream error live — and it is the capability set that most directly determines whether we can scale into new markets without scaling headcount at the same rate. This role owns that problem end to end.

You will operate as a group-level product leader within an Agile environment: setting direction across multiple teams, managing and developing a small team of product managers, and translating a Core Market strategy into an executable, sequenced roadmap. You will spend as much time with operations leaders, carrier partners, and brokers as you do with engineering. This is a build-and-scale role, not a maintenance role.

What You’ll Own

• Core Market post-sale capability strategy — enrollment, group onboarding and installation, eligibility and member maintenance, renewals, and service workflows.
• Enrollment modernization — a multi-release program to replace manual, document-driven enrollment with a digital, validated, self-service experience for employers and their employees, including carrier connectivity and data exchange.
• Market expansion enablement — ensuring post-sale capabilities are configurable enough to support entry into new states, new market segments, and new carrier relationships without bespoke rework.
• A small, high-leverage product team — hiring, coaching, and setting the bar for product craft.

Responsibilities

Strategy & Roadmap

• Define and maintain the vision, strategy, and multi-quarter roadmap for post-sale capabilities, grounded in client research, operational data, and competitive intelligence.
• Build and defend the business case for major investments: quantify the cost of the current state, model expected outcomes, and be explicit about tradeoffs.
• Partner with leadership on market expansion planning, identifying capability gaps that must close before entering a new market.
• Maintain a clear point of view on build vs. buy vs. partner across the ben-admin and enrollment ecosystem.

Execution

• Own backlogs for your value stream; prioritize and communicate sequencing rationale transparently for all levels of stakeholders.
• Represent your capability areas within the Agile development cycle staying ruthlessly focused on Objectives and Key Results.
• Partner across Product & Engineering to keep dependencies visible and resolved early.
• Break large investments into thin, releasable increments across teams that deliver measurable value rapidly rather than at the end of a program.

Team Leadership

• Manage, coach, and grow a small team of product managers; set clear expectations for discovery rigor, written communication, and outcome ownership.
• Establish and enforce consistent product practices: problem definition, success metrics, acceptance criteria, and post-launch validation.
• Serve as an escalation point and a decision-maker — unblock your team rather than routing decisions upward.

Stakeholder & Cross-Functional Partnership

• Act as the primary product voice for Sales, Operations, Client Services, and Compliance on all post-sale capabilities.
• Build durable working relationships with carrier partners on data exchange, eligibility feeds, and enrollment integration.
• Run a continuous discovery loop with brokers, employer groups, and internal operations teams; make customer evidence, not opinion, the basis for prioritization.
• Communicate progress, risks, and results to executive stakeholders — leading with the “so what,” not the activity log.

Outcomes & Measurement

• Define the metrics that matter for enrollment and post-sale performance.
• Establish Objectives and Key Results for multiple teams through the Agile deliver cycle.
• Instrument what you ship, review the data, and act on it — including sunsetting or reversing what does not work.

Requirements

• 10+ years of product management experience (typically 10–15), including meaningful time owning complex, workflow-heavy in B2B & B2C products.
• Recent, substantive experience in insurance and employee benefits — health, ancillary, or a closely adjacent domain. You should already understand group enrollment, eligibility, carrier data exchange, and the broker–GA–carrier relationship.
• Demonstrated people leadership — you have managed product managers, not just influenced cross-functional teams.
• Proven track record delivering large, multi-team initiatives in an Agile at scale environment (SAFe or equivalent), including operating within PI cadence and portfolio governance.
• Strong analytical fluency: comfortable defining metrics, working directly with product analytics and operational data, and using both to drive decisions.
• Excellent written communication. You can make a complex, contested tradeoff legible to an executive audience in one page.
• Experience modernizing or replacing legacy operational workflows — including the organizational change management that comes with it.
• Fluent in daily AI tooling use as part of the product craft — prototyping against MCP-connected APIs, analyzing product usage data, and drafting specs.

Preferred Qualifications

• Track record delivering solutions across both B2B and B2C value chains — you have built for the buyer and the end consumer, and you understand how differently those two audiences must be served. Strong plus for this role: our clients are employers and brokers; our end users are their employees.
• Hands-on experience with benefits administration or enrollment platforms (e.g., Employee Navigator, Ease, bswift, PlanSource) and with EDI 834 / API-based carrier connectivity.
• Familiarity with ACA, ERISA, HIPAA, and state-level compliance requirements as they shape enrollment and eligibility.
• Experience applying AI and automation to reduce manual operational work in a regulated environment.
• SAFe Product Manager / POPM certification.
• Experience supporting geographic or segment expansion for a distribution or insurance services organization.

What Success Looks Like

• First 60 days — You have built a clear, evidence-based picture of the current post-sale experience, including where cost, cycle time, and client friction actually sit. You know your team, your operators, and your top three problems.
• First 3 months — A sequenced enrollment modernization roadmap is agreed with leadership and in flight, with the first releasable increments delivered and instrumented. Your team is operating with a consistent product practice.
• First 6 months — Measurable improvement in enrollment cycle time and straight-through processing. Post-sale capability gaps for planned market expansion are identified, prioritized, and closing.

Pay

Annual Salary Range: $200,000 - $230,000 per year plus productivity bonus. The actual compensation may vary from posting based on work experience, education, skill level, and/or geographic location.

Benefits

• Merit increases
• Paid holidays
• Paid Time Off
• Medical, dental, vision insurance
• Short- and long-term disability benefits
• 401(k) + match
• Life insurance