Product Manager - Underwriting Operations

Ledgebrook is an InsurTech MGA on a mission to bring Specialty insurance into the modern era. Burdened with legacy technology and processes, the industry has not kept pace with the speed of innovation seen in other sectors. Positioned at the cutting edge of the next generation of InsurTech, Ledgebrook offers the best of both worlds: innovative world-class technology deployed by a leadership team armed with over 100 years of insurance expertise.

Our long-term vision is to become a diversified full stack Specialty re/insurer competing with legacy carriers in product lines & markets across the globe. To get there, Ledgebrook builds its premium base by rolling out a new Specialty product every ~6 months until we prove enough traction to raise a balance sheet, become a full stack carrier and eventually compete in the reinsurance markets. Our initial product is a domestic primary and excess GL E&S policies sourced via wholesale brokers.

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. 

Ledgebrook is a fully-remote US based company backed by top venture and family office investors including Brand Foundry, American Family Ventures, Duquesne Family Office, and Stephens Group. We’re a fully remote team prioritizing impact, ownership, and collaboration.

We’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.

Tech Stack

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

What you’ll do

• 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.

Must haves

• 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.

Nice to haves

• 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.

• Competitive salary + meaningful equity ownership
• Completely remote, flexible schedule, and monthly coworking gatherings
• Unlimited paid time off
• Work with an ambitious, smart, fun team to transform a $1T global industry
• Ownership, autonomy, purpose