Director Insurtech Jobs in Wisconsin (NOW HIRING)

Overview

RealPage is seeking a strategic, execution-driven Director of Product Management to lead the AI strategy for our Renter’s Insurance portfolio. This role owns the transformation of eRenterPlan, AssetProtect, PolicyValidator, and future offerings into an AI-native portfolio, and is directly accountable for policy count aand revenue growth as a result of these initiatives. The Director sets the AI strategy and roadmap across the portfolio, leads and develops a team of Product Managers and serves as the primary voice for insurance AI strategy in front of executive leadership, the Lumina platform organization, our clients and RealPage’s AI Governance boards.

You will translate a multi-year AI strategy into a resourced, sequenced portfolio of bets and build and coach the team that executes it, while representing the Insurance portfolio within and across the broader RealPage AI strategy and governance infrastructure.

This role is ideal for a product leader who combines strategic vision with organizational leadership, has operated in regulated or AI-forward environments, and wants to build both a category-leading AI strategy and the team that delivers it.

Responsibilities AI Strategy & Vision Ownership

• Own and evolve the end-to-end AI strategy for the insurance portfolio into a sequenced, resourced portfolio of AI-driven bets in support of double-digit year-over-year revenue growth
• Define how AI shows up across the portfolio (as confidence layer, economic engine, and narrative) and ensure every initiative is judged against required-unit growth, revenue growth, attach, persistency, and loss-ratio impact, not AI adoption for its own sake.
• Represent the insurance AI strategy to executive leadership and the C-suite, including the business case, investment shape, risk register, and quarterly progress against the growth target.

Team Leadership & Organizational Build-Out

• Lead, coach, and grow a team of Product Managers, providing direction, unblocking execution, and holding the team accountable to outcomes.
• Set team OKRs, conduct performance reviews, and own compensation and promotion recommendations for direct reports.
• Establish structured, repeatable processes for roadmap prioritization, PRD quality, and go-to-market readiness across the team.

Platform & Partner Leadership (Lumina)

• Own the relationship with the Lumina AI Workforce team (Resident, Operations, and Finance Agents), converting a seat at the governance table into committed roadmap prioritization for insurance-shaped work.
• Negotiate and lock shared OKRs with Lumina product partners and elevate and resolve roadmap conflicts when insurance priorities compete with other platform workstreams.

Customer & Market Insight

• Stay directly connected to PMC and resident pain points through regular client conversations and review of behavioral, support, and direct survey data, ensuring AI investments are grounded in real user needs rather than internal narrative.
• Represent the voice of residents and PMC stakeholders in executive and Lumina platform discussions, ensuring customer experience trade-offs are weighed alongside growth and efficiency goals.

Business Performance & Executive Accountability

• Own the portfolio’s core business outcomes - enrollment, revenue growth, churn and persistency, premium/policy economics, and customer experience - and the P&L case for AI investment, including modeling unit economics and defending the business case to finance and executive leadership.
• Partner with sales leadership and product marketing to retool the competitive narrative and battlecards as AI capability ships, closing the gap between capability and market perception.

Qualifications Required

• 8+ years of product management experience, including 1+ years directly leading and developing product managers or a product team.
• Demonstrated experience setting and executing an AI-driven product strategy, ideally in fintech, insurtech, proptech, SaaS, or another regulated or platform-dependent environment.
• Track record owning P&L or business-case accountability for a product portfolio, including presenting to and influencing senior executives and the C-suite.
• Experience operating in or alongside a regulated business, including partnering with legal/compliance on governance, fairness, and audit requirements for AI systems.
• Strong experience negotiating roadmap priority and shared commitments with partner platform teams outside direct span of control.
• Excellent executive communication skills, including comfort presenting strategy, risk, and trade-offs to senior leadership.

Preferred

• Deep knowledge of insurance, renter’s insurance or related regulatory environments.
• Experience with embedded or agentic AI platforms and orchestrating product work through a platform team you do not directly control.
• Prior experience hiring, mentoring, and developing product management talent.

Attributes of a Successful Candidate

• Strategic leader who can hold a multi-year vision while driving disciplined, sequenced 12-month execution.
• Organization builder who develops talent and creates the operating model a strategy needs to succeed.
• Executive communicator who translates complex AI and regulatory trade-offs into a clear business narrative.
• Influence-driven operator who can secure priority and commitments from partner teams without formal authority over them.
• Risk-calibrated thinker who balances velocity with the governance rigor a regulated business demands.
• Data-driven decision maker who ties every AI investment back to a measurable business outcome.

SALARY AND BENEFITS

• RealPage provides a competitive salary package along with a comprehensive benefit plan that includes:
• Health, dental, and vision insurance.
• Retirement savings plan with company match.
• Paid time off and holidays.
• Professional development opportunities.
• Performance-based bonus based on position.

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Compensation may vary depending on your location, qualifications including job-related education, training, experience, licensure, and certification, that could result at a level outside of these ranges. Certain roles are eligible for additional rewards, including annual bonus, and sales incentives depending on the terms of the applicable plan and role as well as individual performance.

Equal Opportunity Employer: RealPage Company is an equal opportunity employer and committed to creating an inclusive environment for all employees.

Pay RangeUSD $121,000.00 - USD $206,000.00 /Yr.