Senior AI Product Manager

Ledgebrook is an AI-native specialty insurance platform. When a business needs coverage that is custom and complex, its broker comes to us, and our underwriters give them an answer, often in hours rather than weeks.

We built our technology from scratch, with AI in it from the first line of code. The technology helps price the risk; the underwriter uses their judgment to decide. There are always two hands on the wheel.

We are insurance industry insiders, and we eat our own cooking: Ledgebrook writes the policy and shares the risk through our own carrier, Ledgebrook Specialty, rated A- (Excellent) by AM Best. We work exclusively through wholesale brokers.

Our vision: to make the wheels of insurance spin faster.

At Ledgebrook, everything we do is driven by our culture: Care, Strive, Thrive Together. To succeed in modernizing the industry, we must first succeed in changing the way we do business. Talent density is our north star—fewer, better people working together as one. To that end we’ve replaced all individual incentives with generous equity packages—we play as a team, we win as a team. Everyone benefits handsomely from Ledgebrook’s success.

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.

We’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 decisions

• A passion for building technology that drives real business impact and elevates customer experience
• A desire to lead by example, mentoring others while staying connected to the code and architecture
• Intellectual curiosity and a drive to improve processes and systems rather than accepting the status quo
• The ability to balance strategic thinking with tactical execution in a fast-moving environment
• A strong drive and desire to win together as a high-performing team
• A moral compass to “do the right thing, period” — we have zero tolerance for toxic behaviors

Must 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 environments
• Strong understanding of machine learning concepts including Agentic Workflows, NLP, and LLMs
• Experience working with modern LLM platforms (e.g., Claude, Hugging Face, AWS Bedrock)
• Familiarity with agentic AI frameworks such as LangGraph, LlamaIndex, or CrewAI
• Experience working with human reviews of AI workflows utilizing tools such as A2I
• Strong 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 industries
• Background in scaling AI/ML initiatives in a startup or high-growth environment
• Prior hands-on engineering experience in AI/ML or data science

• Full remote flexibility and asynchronous work culture.
• Unlimited PTO and fully paid sick leave.
• Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options.
• Additional financial protection and retirement benefits, including a a 401(k), company-paid life insurance, and disability coverage.

For Candidates Applying From The U.S. and Canada

Please note: This position is open to candidates who are authorized to work in the United States or Canada, without the need for current or future employer-sponsored work authorization. We are unable to offer sponsorship at this time."

• Base 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.