[Hiring] Senior AI Product Manager @Integrated Specialty Coverages

Role Description

We are seeking a Senior AI Product Manager to own major product areas and drive them forward using an AI-first approach to discovery, prototyping, and delivery. Reporting to the VP of Product, you will lead a small, high-velocity squad (typically 1 PM + 2 engineers) to solve complex insurance operations problems by building AI-powered solutions — starting with workflow automation and progressing to full platform integration. This is not a role where you write requirements and hand them off. You will build functional prototypes with AI tools, validate them directly with users, and iterate rapidly. You’ll work at the intersection of AI capabilities and insurance domain problems, turning manual processes into intelligent, automated workflows.

Position Responsibilities

• AI-First Product Development:
  • Use AI tools (LLMs, AI coding assistants, computer use agents, API integrations) daily to prototype solutions, validate hypotheses, and accelerate delivery.
  • Drive the development pattern: automate the user’s existing workflow first (computer-level automation), then move validated solutions into the platform for scale.
  • Manage multiple parallel workstreams simultaneously, leveraging AI to maintain velocity across 3-5 initiatives at once.
• Define Product Vision and Strategy:
  • Define product vision and strategy for major product areas, with AI capabilities as a core lever for achieving business outcomes.
  • Identify opportunities where AI can replace or dramatically improve existing manual workflows.
  • Shape the long-term product roadmap, balancing quick automation wins with strategic platform investments.
• Lead High-Velocity Squads:
  • Lead a small, cross-functional squad (1 PM + 2 AI-enabled engineers) with full ownership from discovery through delivery.
  • Work directly alongside engineers — reviewing AI-generated code, testing integrations, and unblocking the team in real time.
  • Drive rapid iteration cycles measured in days and weeks, not months.
• Drive Customer-Centric Discovery:
  • Embed directly with operational teams (underwriters, brokers, operations staff) to understand their workflows firsthand.
  • Build working prototypes to test solutions with real users before committing to full development, using AI tools to compress the discovery cycle.
  • Make data-driven decisions focused on measurable business outcomes over feature delivery.
• Collaborate with Technical Teams:
  • Work closely with engineering leadership on AI tooling strategy, development patterns, and technical feasibility.
  • Participate actively in technical discussions — evaluating APIs, data flows, and system integrations well enough to evaluate tradeoffs and unblock the team.
• Mentor Junior Talent:
  • Guide and mentor junior product managers on AI-first product development practices, fostering a culture of continuous experimentation and hands-on building.
• Influence Broader Product Direction:
  • Act as an internal thought leader, demonstrating what’s possible with AI-enabled development and raising the bar for the team.
  • Identify opportunities for innovation and growth in the Insurtech space.
• Build Stakeholder Relationships:
  • Communicate progress, risks, and decisions to leadership through SteerCo and other governance forums.
  • Build relationships with business unit leaders, translating their operational needs into AI-powered solutions.

Qualifications

• 4-7 years of product management experience in a technology-driven environment.
• Insurance or Insurtech experience is a plus but not required — AI capability is the priority.

Requirements

• AI Proficiency (Required): Demonstrated, hands-on experience using AI tools (LLMs, AI coding assistants, automation frameworks) to build or prototype real solutions — not just familiarity with the concepts.
• Technical Background: Strong understanding of software development, APIs, system integrations, and data flows.
• Leadership Skills: Proven ability to lead cross-functional teams, influence without authority, and drive complex initiatives to successful outcomes.
• Communication: Excellent communication and interpersonal skills, with the ability to engage both technical and non-technical stakeholders effectively.
• Mentorship: Demonstrated ability to mentor and develop junior team members.
• Education: Bachelor’s degree in Computer Science, Engineering, Business, or a related field.

Benefits

• Employee Ownership Program - every eligible employee shares in the financial rewards that grow when the company grows.
• Professional development opportunities.
• Owner Referral Program.
• Work from home reimbursement for remote/hybrid roles.
• Burnalong digital health and wellness platform.
• Canary emergency financial assistance program.
• Comprehensive medical, dental, vision.
• Life/AD&D Insurance.
• Confidential, Employee Assistance Program.
• Health Savings Account, includes company contribution.
• Short-term disability.
• Voluntary benefits - supplemental accident, critical illness, hospital insurance.
• Employee discounts.
• 401(k) Plan with company match contribution.
• Various Time Off Programs.
• 11 company paid holidays.