Product Manager - Underwriting Operations

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.

Rawanna DasilvaWe’re looking for a talented Product Manager to lead the strategy, execution, and delivery of our operations application. You’ll partner closely with engineering and Underwriting Operations leadership to define priorities, manage sprints, and ensure our Underwriting Operations roadmap aligns with company goals.

The ideal candidate thrives at the intersection of technology and business, comfortable writing user stories, coordinating across teams, and driving delivery for high-impact internal systems.

• Product Tools: Jira, Confluence, Loom, Slack, Figma, LaunchDarkly
• Reporting/User Metrics: PowerBI, Userpilot

• →Own the product lifecycle for Ledgebrook’s Underwriting Operations initiatives from discovery through delivery and measurement.
• →Lead agile ceremonies (sprint planning, retrospectives, standups) and manage Jira: creating, refining, and validating stories to ensure clarity and readiness for release.
• →Partner with engineering leads to translate complex technical initiatives into clear deliverables, balancing strategic priorities with day-to-day execution.
• →Collaborate with stakeholders across engineering, actuarial, underwriting, finance, and operations to understand needs and define roadmap priorities.
• →Define success metrics and use data to track outcomes, improve processes, and guide investment decisions.
• →Ensure technical readiness for releases, coordinating QA, documentation, and stakeholder communication.
• →Lead roadmap planning, aligning quarterly and annual objectives with company OKRs and evolving business needs.
• →Champion internal adoption of new tools, ensuring teams across the company derive measurable value.
• →Drive continuous improvement in team velocity, delivery predictability, and agile maturity.

You combine structured product thinking with a systems mindset. You can bridge technical depth with business context, turning complex problems into solutions with tangible business impact. You’re organized, collaborative, and thrive on making teams more effective. 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.

• 5+ years of product management experience, ideally supporting application teams.
• Proven success leading agile software development teams and managing workflows (epics, sprints, story validation).
• Strong communication and stakeholder management skills, able to synthesize competing priorities into a clear plan.
• Comfort with technical topics such as APIs, cloud infrastructure, data pipelines, and system reliability.
• Analytical and metrics-driven approach to prioritization and success measurement.
• Experience managing complex cross-functional projects from ideation through delivery.
• Ability to navigate ambiguity and provide clarity for engineering and business partners.

• Familiarity with the Insurance Industry and its processes (Underwriting, Claims, etc.)
• Understanding of cloud infrastructure (AWS, Terraform, ECS, IAM, networking).
• Experience in Insurtech or another regulated, data-heavy industry.
• Hands-on familiarity with defining application design (Figma, Sketch, XD, etc.)
• Experience driving adoption of internal tooling or developer productivity platforms.
• Background in agile coaching, process design, or operational excellence.
• Coordination of large scale software rollouts across multiple teams.

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

Ledgebrook may use Artificial Intelligence (“AI”) as part of the job application process, including to assist us in evaluating your application. AI is used as a support tool, and hiring decisions are made by human recruiters. By submitting your information, you acknowledge that the company may use AI tools as part of our evaluation. If you need a reasonable accommodation or alternative review process because of a disability or other legally protected basis, contact hiring@ledgebrook.com. Requesting an accommodation will not negatively affect your application.