Tax Senior Paralegal

Arnold Porter; Worcester (VT); Remote; USD 70,000 - 110,000; Full time

Benefits offered by this job

Health, dental and vision coverage

Paid time off, paid parental leave

401(K) plan with employer matching

Wellness benefits

Equity opportunities

Job summary

Jerry.ai is hiring a Legal Researcher (Remote) to join our in-house legal team. You will research federal and state regulatory, consumer protection, and product-related questions, turning findings into practical recommendations for business leaders.

You will draft and review agreements with partners and vendors, support license requirements, and help ensure compliance across product and operations. A JD or LLM with strong academics is required.

Qualifications

• JD or LLM with a record of high academic performance.
• Experience drafting or reviewing contracts via coursework, a clinic, an internship, or work.
• Strong legal research and writing skills; translate complex analysis into practical recommendations.
• Excellent organization and ability to manage multiple matters and deadlines.

Responsibilities

• Draft and review agreements with partners and vendors; support negotiations through execution.
• Research federal and state regulatory, consumer protection, insurance, privacy and other legal questions; turn findings into actionable recommendations.
• Support licenses and recurring regulatory requirements; help build systems to keep them current.
• Review features, flows, and processes with Product, Engineering, and Operations; translate legal requirements into product decisions.
• Investigate complex consumer escalations and regulatory inquiries; propose scalable fixes and training for compliance.
• Help design and improve Jerry’s legal and compliance policies, procedures, and controls to manage risk.
• Take on new legal and regulatory questions as Jerry launches products and expands its business.

Skills

Legal research

Legal writing

Contract drafting

Project management

Communication

Education

J.D. or LLM

Job description

Legal Researcher (Remote)

Full‑time, Remote (United States)

Job Description

More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. At Jerry.ai, we are building the first app to manage it all. Since launching in 2019, we’ve reached 5M+ customers, raised $240M+, scaled revenue 70X, and achieved profitability in 2024. Operating across the US and Canada brings a steady flow of regulatory, consumer protection, and product questions that need clear legal answers fast. As our Legal Researcher, you’ll work closely with our Legal Counsel and partner with teams across Jerry to research hard questions and turn your findings into decisions the business can act on. This role is built for high‑performing law graduates who want a rigorous in‑house legal career outside the law firm path. It’s highly hands‑on: you’ll draft and negotiate agreements with partners and vendors, research licensing and regulatory requirements, support product and compliance reviews, and help solve new legal questions as the business grows. If you succeed, Jerry’s leaders make faster, better‑informed decisions on legal risk, and you’ll have owned work that shapes how the company grows.

What You’ll Own

• Draft and review agreements with partners and vendors, identify key issues, and support negotiations through execution.
• Research federal and state regulatory, consumer protection, insurance, privacy, and other legal questions, and turn your findings into clear, practical recommendations business leaders can act on.
• Support the licenses and recurring regulatory requirements needed for Jerry’s products and operations, and help build systems that keep them current.
• Review features, flows, and processes with Product, Engineering, and Operations, and support translating legal requirements into product decisions.
• Investigate complex consumer escalations and regulatory inquiries, identify root causes and potential legal issues, propose scalable fixes, and turn recurring issues into company‑wide compliance training.
• Help design and improve Jerry’s legal and compliance policies, procedures, and operational controls to manage legal and business risk.
• Take on new legal and regulatory questions as Jerry launches products, enters partnerships, and expands its business.

Who You Are

• You can read a regulation, work out what it means for a product decision, and explain it clearly and concisely.
• You find the answer yourself before asking for it, and you track every open item until it’s resolved.
• When you see the same manual task twice, you start looking for a way to automate it.
• You review every contract and filing with total precision and keep your own system so no deadline slips.
• You keep people updated without being chased, flag blockers early, and make sure teammates know what happens next.
• You’re as ready to clean up a tracker or follow up on an overdue item as you are to dig into a difficult legal question.

What You’ll Bring

• A JD or LLM, with a record of high academic performance.
• Experience drafting or reviewing contracts, through coursework, a clinic, an internship, or work.
• Strong legal research and writing skills, with the ability to turn complex analysis into clear, practical recommendations.
• Strong organization and project‑management skills, with the ability to manage multiple matters and deadlines at once.

EEO Statement

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us.

Benefits

• Health, dental and vision coverage.
• Paid time off, paid parental leave.
• 401(K) plan with employer matching.
• Wellness benefits.
• Equity opportunities may also be part of your total rewards package.