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 decades 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 will build our 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 as well. Our initial product will be 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 investors including Brand Foundry & American Family Ventures.

Industry: Insurance
Company Size: 51-200 employees

Ledgebrook

Savvy Admin PROD

**The Opportunity **

We’re hiring a **Paralegal ** to support our Legal, Regulatory & Compliance function as we scale.

Reporting to the Head of Insurance Compliance and working closely with our General Counsel, this role will partner cross-functionally across Underwriting, Operations, and Finance to ensure smart, swift, and compliant decision-making across the business.

This is a high-ownership role inside a fast-moving, venture-backed environment.

**What You’ll Do **

- Conduct legal research across statutes, regulations, and case law

- Prepare and manage legal documentation, regulatory filings, and internal records

- Maintain organized contract repositories and audit-ready files

- Support litigation and discovery processes

- Coordinate legal correspondence and stakeholder communications

- Manage moderately complex legal matters independently

- Partner across business units to ensure regulatory alignment

- Improve workflows and documentation standards as we scale

**What We’re Looking For **

- Strong judgment and discretion handling sensitive information

- High ownership mentality and personal accountability

- Organized, detail-oriented, and responsive

- Comfortable operating autonomously in a fast-paced environment

- Clear written and verbal communication skills

- Collaborative mindset with a “do the right thing, period” attitude

**Nice to have: **

Insurance industry exposure, regulatory familiarity, contract review experience, or experience in high-growth environments.

**Why Ledgebrook? **

- Competitive salary + meaningful equity

- 100% employer-paid health insurance option (U.S.)

- 401(k), dental, vision

- Fully remote with flexible hours

- Unlimited PTO

- High talent density, zero individual incentives — we win as a team

**Important: ** This role is open to candidates authorized to work in the U.S. without sponsorship.

If you’re looking for ownership, impact, and the opportunity to help build something differentiated in Specialty insurance — let’s connect.

Paralegal

The Athletic delivers powerful stories and smart analysis that bring sports fans closer to the heart of the game. From breaking news and live commentary, to deeply-reported long reads and exclusive interviews, subscribers rely on The Athletic for every sports story that matters. Acquired by The New York Times in 2022. 

Learn more about career opportunities at The Athletic: https://theathletic.com/careers/

Industry: Online Media
Company Size: 501-1,000 employees

The Athletic

**About Us**

Powered by one of the largest global newsrooms in sports media, The Athletic brings sports fans the most comprehensive stories about the teams, sports and athletes they love. The Athletic’s newsroom of 500+ full-time staff delivers in-depth coverage of hundreds of professional and college teams across more than 47 North American markets and all 20 football clubs in the English Premier League, as well as many Championship clubs.

**About This Role**

The Vice President role requires an experienced attorney who will act as a deputy for the General Counsel of The Athletic, provide expert legal and business-forward counsel and manage a team that includes a transactional lawyer and a legal professional. This is a hybrid role based in New York City, reporting to the General Counsel for The Athletic and supporting The Athletic’s leadership team while working alongside members of The New York Times Company legal team.

**Responsibilities**

- Serve as a senior legal leader for The Athletic, assessing risk on a broad range of business and legal matters, making executive recommendations and driving matters to resolution, escalating to the General Counsel as appropriate.

- Provide legal support to The Athletic’s digital product organization, including teams across product, design, data and engineering, on compliance with laws, assessing issues and crafting risk-based solutions that balance legal requirements with business objectives.

- Act as the primary legal partner for the product development team on AI and generative AI legal issues offering risk mitigation strategies across multiple jurisdictions, and collaborating with cross-functional teams to align technology use with company strategy.

- Work closely with The Athletic leadership in coordinating and advising on major legal and regulatory matters, handling special projects and initiatives, developing and implementing team operations and budgeting improvements, identifying efficiency opportunities, helping coordinate on compliance activities, policy development, risk assessment processes and training programs.

- Collaborate with subject matter experts across technical and non-technical teams, New York Times Company lawyers and stakeholders to consolidate multiple legal and business considerations into clear guidance in service of company strategy and product goals.

- Provide oversight on commercial transactions and directly manage the team that provides commercial legal support and legal operations for The Athletic’s business.

- Stay informed about legal decisions, statutory changes, and market and industry trends, and, in coordination with the team, advise clients and recommend proactive action when necessary.

**Requirements**

- Undergraduate and J.D. degrees, and a member of good standing of the New York bar or the equivalent.

- 10+ years of relevant work experience that includes experience with product counseling and the handling of a broad range of intellectual property, technology, data privacy and commercial transactions, with increasing levels of responsibility.

- Experience advising product and other teams through complex matters, with diverse stakeholders and competing interests.

- Experience managing a team and achieving results in a high pressure environment.

- Ability to contribute to discussions of general business issues, to work well with a wide range of clients from senior management to operating personnel, and to work independently as well as to lead a project from conception to completion.

- Ability to analyze complex legal material and communicate implications in clear and simple language, along with a clear recommendation for an appropriate course of action.

- Strong organizational skills and ability to balance competing demands.

- Experience in generative AI and AI counseling and compliance

**Preferred Qualifications**

- Experience acting as a member of a senior leadership team

- Experience working on a fast-paced in-house legal team

- Experience advising engineering, design or other technical teams

- Experience in news, media and/or journalism

The annual base salary range for this role is $230,000 - $260,000 USD. The total compensation offered for this position may vary based on factors such as education, experience, skills, and location.

~~For roles in the U.S., dependent on your role, you may be eligible for variable pay, such as an annual bonus and restricted stock. Benefits may include medical, dental and vision benefits, Flexible Spending Accounts (F.S.A.s), a company-matching 401(k) plan, paid vacation, paid sick days, paid parental leave, tuition reimbursement and professional development programs.~~

~~For roles outside of the U.S., information on benefits will be provided during the interview process.~~

~~The Athletic Media Company is an equal opportunity employer and enthusiastically encourages people from all backgrounds and experiences to apply. The Athletic will consider all applicants without regard to race, religion, color, national origin, ancestry, physical and/or mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, transgender status, age, sexual orientation, military or veteran status, or any other protected characteristic under applicable law.~~

~~Click here to review our ~~Applicant Privacy Notice~~, which describes how and when The Athletic Media Company collects, uses, and shares certain personal information of job applicants and prospective employees.~~

~~Beware of fraudulent job recruiting schemes! Our recruiters use ~~~~careers@theathletic.com ~~~~exclusively, and our team members will use an email address with @ ~~~~theathletic.com ~~~~domain. We do not conduct interviews via text or instant message and we do not ask candidates to download software, to purchase equipment through us, or to provide sensitive personally identifiable information, such as bank accounts or social security numbers. If you have been contacted by someone claiming to be a member of the recruiting/HR team at The Athletic but operating from a different email address about a job offer, please report it as potential job fraud to the law enforcement and to ~~~~people@theathletic.com ~~~~. ~~

VP, Legal

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