Technical Project Manager (Infrastructure)

Description

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.

About the Role

We are seeking a Senior Technical Program Manager (TPM) to own the end-to-end delivery of complex technology initiatives and drive execution at scale. You will operate at the intersection of development, product, DevOps, IT, security, and compliance, leading multiple projects, managing dependencies, mitigating risks, and translating strategy into structured plans with clear milestones and success metrics.

You will play a key role in shaping engineering excellence and optimizing how teams build and release software in a high growth startup environment. This role is ideal for someone who started in engineering (development, QA, DevOps, SDET, etc.) and has evolved into leading large, cross-functional programs that deliver measurable business outcomes.

About you

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 to deliver a world-class service experience to every team member, ensuring technology is an enabler, not a barrier, to doing great work
• Intellectual curiosity and a desire to improve processes and systems versus being satisfied with the status quo
• A strong operational mindset and sense of urgency to balance getting it right with getting it done right now
• A drive to win together as a high-performing team
• A moral compass to “do the right thing, period”. We have zero tolerance for toxic behaviors

Requirements

• 5–10 years of experience in an engineering organization across areas such as software development, QA, automation, DevOps, or release engineering
• Proven experience as a technical program manager, or similar role in a fast-paced environment
• Demonstrated success leading large-scale, cross-team engineering programs with significant business impact
• Strong technical foundation with the ability to understand system architecture, trade-offs, and engineering constraints
• Experience driving engineering infrastructure or platform initiatives across multiple teams
• Data-driven, with experience using OKRs, KPIs, dashboards, and reporting frameworks
• Proficiency in SDLC and program tracking tools such as JIRA and Jellyfish
• Track record of improving engineering processes, delivery predictability, and operational efficiency
• Excellent communication skills, with experience influencing and presenting to executive-level stakeholders
• Experience working with globally distributed teams, with strong cross-cultural collaboration skills
• Ability to influence without authority and drive alignment across competing priorities

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