This is a high-impact AI Product Manager role focused on leading the development of the systems that will power Ledgebrook’s fully autonomous underwriting engine. You will be responsible for driving the planning, execution, and delivery of complex AI/ML initiatives, working cross-functionally with engineering, product, data, and business teams.You’ll partner closely with engineering, analytics, and business leadership to define priorities, manage sprints, and ensure our AI roadmap aligns with company goals.The ideal candidate thrives at the intersection of technology and business, identifying high value AI use cases, coordinating across teams, and driving delivery for high-impact internal systems.About youWe’re looking for a talented Product Manager passionate about building innovative insurance products that meet the needs of customers and drive business growth, and a proven track record of launching successful products. You have demonstrated a data-driven approach to decision-making and a commitment to delivering high-quality products that meet customer needs. You are able to define and measure key success metrics for products, and use data to inform product strategy and make informed decisionsA passion for building technology that drives real business impact and elevates customer experienceA desire to lead by example, mentoring others while staying connected to the code and architectureIntellectual curiosity and a drive to improve processes and systems rather than accepting the status quoThe ability to balance strategic thinking with tactical execution in a fast-moving environmentA strong drive and desire to win together as a high-performing teamA moral compass to “do the right thing, period” — we have zero tolerance for toxic behaviorsRequirementsMust Haves:5+ years of experience in product management, with a track record of launching successful products.Proven experience delivering AI/ML or data-driven products in production environmentsStrong understanding of machine learning concepts including Agentic Workflows, NLP, and LLMsExperience working with modern LLM platforms (e.g., Claude, Hugging Face, AWS Bedrock)Familiarity with agentic AI frameworks such as LangGraph, LlamaIndex, or CrewAIExperience with human reviews of AI workflows utilizing tools such as A2IStrong leadership and communication skills, with experience leading cross-functional teams.Experience with agile development methodologies.Analytical and data-driven approach to decision-making.Strong understanding of product development processes, from ideation to launch.Excellent problem-solving and project management skills.Nice to Haves:Experience in insurance, fintech, or other regulated industriesBackground in scaling AI/ML initiatives in a startup or high-growth environmentPrior hands-on engineering experience in AI/ML or data scienceBenefitsFull remote flexibility and asynchronous work cultureUnlimited PTO and fully paid sick leaveComprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA optionsAdditional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverageA high degree of ownership, autonomy, and the opportunity to help build and shape a growing companyThe chance to make a meaningful impact while working alongside an ambitious, high-performing teamExposure to the challenges and opportunities of a fast-growing startup environmentCompensationBase Salary Range $150,000-$200,000- This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including experience, qualifications, geographic location and other relevant factors.Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.