Head of Product, Virtual Care

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.

Care, Strive, Thrive Together. To that end we’ve replaced all individual incentives with generous equity packages. 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 - Data & Infrastructure to lead the strategy, execution, and delivery of our core data and platform capabilities. You’ll partner closely with engineering, analytics, and business leadership to define priorities, manage sprints, and ensure our data and infra roadmaps align 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. This role will initially focus on the Data team, with potential to expand oversight to the Infrastructure organization as we scale.

Languages : Python, SQL

Data Stack: Snowflake, dbt, Apache Airflow (AWS MWAA)

Cloud Infrastructure: AWS, Terraform

Own the product lifecycle for Ledgebrook’s data platform and infrastructure 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.

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.

Champion internal adoption of data and infrastructure 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 backend or data platform work into tangible business impact. 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 data, infrastructure, or platform teams.

• Proven success leading agile software development teams and managing workflows (epics, sprints, story validation).
• Comfort with technical topics such as APIs, cloud infrastructure, data pipelines, and system reliability.
• Experience managing complex cross-functional projects from ideation through delivery.
• Familiarity with data stacks (Snowflake, dbt, Airflow, Hevo/Fivetran) and analytics tools (Power BI, Tableau, Looker).

Understanding of cloud infrastructure (AWS, Terraform, ECS, IAM, networking).

Experience in insurtech or another regulated, data-heavy industry.

Prior experience as a technical program manager or data product manager.

Hands-on familiarity with SQL or data visualization tools for basic analysis.

Experience driving adoption of internal tooling or developer productivity platforms.

Background in agile coaching, process design, or operational excellence.

Competitive salary + meaningful equity ownership

• 100% employer-paid health insurance
• 100% remote work, flexible hours