Product Manager – Finance Systems & ERP

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 Product Manager – Finance Systems & ERP to lead the strategy, execution, and continuous improvement of Ledgebrook’s finance technology stack.

This role sits at the intersection of Finance, Accounting, and Engineering. You will own Workday ERP initiatives, billing and invoicing systems, financial data integrations, and future reinsurance back-office infrastructure. Your mandate is to build scalable, audit-ready, automation-first financial systems that support a fast-growing, AI-driven MGA.

You’ll partner closely with Finance leadership, Actuarial, Underwriting, and Engineering to design and deliver the operational backbone of the company.

This is a high-ownership role responsible for turning complex insurance finance workflows into scalable, well-architected systems.

What You’ll Do

Own Finance Systems Roadmap

• Own the product lifecycle for Workday ERP, billing, invoicing, and reinsurance accounting systems.
• Lead roadmap planning aligned with quarterly and annual finance OKRs.
• Translate finance and accounting requirements into scalable system design.

Lead Workday & ERP Initiatives

• Drive implementation and optimization of Workday modules (GL, Revenue, Billing, Cash, Integrations).
• Define integration requirements between Workday and claims, underwriting, actuarial, and reinsurance systems.
• Partner with engineering on EIB, Core Connectors, APIs, and custom integrations.

Billing, Invoicing & Cash Operations

• Own product requirements for premium billing, commissions, cash application, and reconciliation workflows.
• Improve automation in premium-to-cash lifecycle.
• Establish system controls and audit readiness.

Reinsurance Back Office (Future Scope)

• Design scalable systems for ceded premium tracking, bordereaux, recoverables, and reporting.
• Define integration patterns between policy, claims, actuarial, and reinsurance systems.

Execution & Delivery

• Lead agile ceremonies for finance systems initiatives.
• Own Jira workflows for finance tech projects.
• Define acceptance criteria and ensure stakeholder sign-off.
• Coordinate QA, UAT, documentation, and release readiness.

Operational Excellence

• Improve system reliability, financial data integrity, and reconciliation processes.
• Establish KPIs around billing accuracy, close time, automation rate, and data quality.
• Reduce manual finance operations through automation and integration.

Here at Ledgebrook we are passionate about creating a team that is on a continuous learning journey and that shares our excitement about building a company from the ground up. Some of the characteristics we hold dear are:

• 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 in product management, finance systems, ERP implementation, or technical program management.
• Deep experience leading Workday or similar ERP projects (GL, Billing, Revenue, Integrations).
• Experience gathering requirements across Finance, Accounting, and Engineering.
• Comfort working with APIs, data integrations, and system architecture.
• Experience managing cross-functional delivery in a fast-growing company.

Nice to Haves

• Experience in insurance or insurtech (MGA, carrier, broker).
• Strong understanding of accounting workflows (premium, claims, commissions, cash, reinsurance).
• Familiarity with reinsurance accounting and bordereaux processes.
• Understanding of data platforms (Snowflake, dbt) and finance reporting pipelines.
• SQL literacy for validation and reconciliation.
• Experience improving financial close processes or SOX controls.
• Background in operational excellence or process automation.

Important - only for candidates applying from the U.S.:

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

• Competitive salary + meaningful equity ownership
• 100% employer-paid health insurance
• 100% remote work, flexible hours
• Unlimited paid time off
• Work with an ambitious, smart, fun team to transform a $1T global industry
• Ownership, autonomy, purpose