Careers > OPEN POSITION

Paralegal

Remote - US

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’re looking for a talented Paralegal to assist Ledgebrook’s Legal, Regulatory & Compliance function with the delivery of top notch legal, regulatory and compliance services across the organization . You’ll work cross-functionally with various units across Ledgebrook to enable smart and swift-decision making while always doing the right thing.

The ideal candidate is a self-starter with a strong work ethic, good judgement, solid organizational skills, and desire to learn. This role will report to the Head of Insurance Compliance, with opportunities to help the further maturation and buildout of the Legal, Regulatory & Compliance function under the leadership of Ledgebrook’s General Counsel.

What you will do? 

  • Conduct legal research and analyze statutes, regulations, case law, and internal policy documentation.
  • Prepare, review, and file legal documents including pleadings, affidavits, regulatory filings, and other supporting materials.
  • Maintain organized legal files, contract repositories, and documentation databases to ensure audit-ready records.
  • Support litigation and discovery efforts, including document collection, review, and fact investigation.
  • Conduct initial information-gathering interviews and compile summaries for attorney review.
  • Coordinate legal correspondence, manage calendars, and schedule meetings with internal and external stakeholders.
  • Independently manage moderately complex to complex legal matters, escalating only highly sensitive issues as appropriate.
  • Partner cross-functionally with Underwriting, Operations, and Finance to ensure legal alignment and documentation accuracy.
  • Identify opportunities to improve legal workflows, documentation standards, and tracking processes.

About You

We are looking for candidates with a collaborative approach, strong communication skills, and a unique ability to drive strategic, enterprise-level initiatives forward.  Some specific experiences and skills include:

  • A strong sense of ownership and accountability for your work.
  • Intellectual curiosity and a proactive approach to solving problems before they escalate.
  • A desire to continuously improve systems, processes, and documentation standards.
  • Comfort operating with autonomy while knowing when to escalate appropriately.
  • The ability to balance precision and urgency in a fast-paced environment.
  • A collaborative mindset and commitment to building strong cross-functional relationships.
  • A moral compass to “do the right thing, period,” with zero tolerance for toxic behaviors.

Important - note is 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.

Must haves

  • Strong alignment with Ledgebrook’s culture and values.
  • Sound judgment and the ability to handle sensitive information with discretion.
  • Strong work ethic and a high level of personal accountability.
  • Willingness to learn and grow in a fast-paced, evolving environment.
  • Ability to take initiative and operate with ownership.
  • Highly organized with strong attention to detail.
  • Reliable, responsible, and responsive in managing deadlines and communication.
  • Clear and professional written and verbal communication skills.
  • Ability to prioritize effectively and balance urgency with accuracy.
  • Demonstrated attributes of attention to quality and self-discipline.

Nice to have (but not required)

  • Prior exposure to the insurance industry.
  • Experience reviewing or drafting contracts, NDAs, or insurance policies.
  • Awareness of state insurance laws and regulatory requirements.
  • Familiarity with corporate governance matters, including preparing board meeting minutes and board packages.
  • Experience supporting legal operations in a high-growth or regulated environment.
  • Familiarity with the legal/regulatory/compliance regimes in jurisdictions outside the United States.

About Ledgebrook

Ledgebrook is a tech-enabled E&S MGA dedicated to the wholesale distribution channel. Our mission is to provide our wholesale brokers with the fastest, easiest quoting experience while delivering best-in-class pricing and risk selection. Ledgebrook’s guiding principle is to eliminate friction for both our wholesalers and our underwriters.

Our next-gen tech stack supports faster, risk differentiated solutions to be crafted and delivered in response to the fast-paced needs of the E&S market. Our data driven approach seeks to unlock more opportunities and value from every submission received, leading to a faster ‘yes’ more frequently, but may also lead to a quick ‘no’.

We are motivated and structured to move faster than traditional insurance organizations. To fully align business objectives with a long-term view that supports our culture and values, all employees will have the opportunity to participate in company ownership through equity grants. We aim to deliver a highly compelling overall employee value proposition and a total compensation package that couples equity grants with base pay and benefits offerings.

At Ledgebrook, as a unified team of company stewards, we will Care, Strive and Thrive together!

What Ledgebrook can offer you

Competitive salary

and meaningful equity ownership

Health Insurance

100% employer-paid option available

Additional benefits

available include 401k plan,  dental, vision & other options

Remote work,

flexible hours

Unlimited

time off policy

Ownership,

autonomy, purpose

What Ledgebrook can offer you

Competitive salary

and meaningful equity ownership

Ownership,

autonomy, purpose

Remote work,

flexible hours

Unlimited

time off policy

Ledgebrook is proud to be part of

How to Apply

Ledgebrook’s journey has just begun and you’ll have the opportunity, along with our growing team, to help navigate our course.

Are you up for joining the Ledgebrook journey? If so, apply now!

Apply Now

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