• Draft and organize trust administration documents • Assist with execution of trust plans • Provide support on estate planning and probate administration matters • Review legal documents and ensure accuracy and compliance • Support attorneys with ongoing case management and workflow organization • Assist with general legal drafting and research as needed

• Be a trusted advisor to the Executive Leadership Team, HR/People Team, and business leads across the company on the people decisions that matter most • Lead a modern approach to employment risk management, investigations, and governance • Help design and scale policies, training, and tools that make it easier to do the right thing, the right way • Translate complex employment law concepts into clear, actionable guidance for HR/People leaders and managers across performance management, discipline, terminations, accommodations, leaves, wage and hour, remote work, and other employment issues • Act as a thought partner on program and policy design (e.g., performance, hiring, RIFs/restructuring), ensuring decisions are both compliant and aligned to business strategy and culture • Provide risk-calibrated options, clearly framing legal risk, business impact, and trade-offs instead of simple “yes/no” answers • Oversee or conduct internal workplace investigations (harassment, discrimination, retaliation, ethics, and other complex matters), ensuring thorough, timely, and balanced fact-finding with clear recommendations and documentation • Manage demand letters, and pre-litigation matters in partnership with external counsel, balancing legal strategy, business objectives, and employee experience • Develop and maintain frameworks, playbooks, and escalation paths that help HR/People and leaders proactively identify, assess, and manage employment risk • Draft, review, and update employee handbooks, policies, and agreements (e.g., arbitration, severance, restrictive covenants) to align with evolving federal, state, and local requirements • Monitor legal and regulatory developments (e.g., pay transparency, leaves, wage and hour, AI in employment decisions, privacy) and translate them into practical changes to policies, processes, and tools • Help define a scalable, modern governance model that balances business needs, employee experience, and legal compliance with the right level of rigor, consistency, and documentation • Design and deliver training for HR/People, managers, and leaders on investigations, documentation, performance management, accommodations/leave, anti-harassment, and other employment topics • Build self-service tools and guidance (FAQs, playbooks, templates) so HR/People and business partners can handle routine issues confidently and escalate the right issues at the right time • Use case trends and insights from HRIS and case management systems to inform training, policy updates, and leadership behavior • Partner closely with HR/People, Legal, Compliance, Internal Audit, IT, Security, and external counsel to ensure decisions are coordinated, informed, efficient, and business-aligned • Contribute to People and enterprise initiatives (e.g., AI in HR, modern work practices, remote/hybrid strategies) by advising on employment law, privacy, and ethical implications • Model a team-first, low-ego, high-judgment way of working that builds trust across functions

We’d love to hear from you if you like: - Making a big impact on day one with a Forbes Top Startup Employer. - Working at a startup that has traction: $240M in funding and 60x revenue growth in 5 years. - Mentorship from serial entrepreneurs and brilliant leaders who have scaled companies like Amazon, Better, LinkedIn, McKinsey, BCG, Bain - Meritocracy: We promote based on performance, ownership, and results, not tenure. About the Opportunity: We are looking for a highly resourceful and ambitious Operations Associate to join our lean, fast-paced legal team. This isn't a traditional "administrative" legal role. We are looking for someone with a product-focused mindset who doesn't just follow a process but seeks to automate and scale it. The person who succeeds in this role is a natural driver: someone who owns a project from start to finish, solves complex problems without a manual, and has the grit to thrive in a startup environment. If you are eager to sit at the intersection of law, technology, and AI-driven efficiency, we want to hear from you. What You'll Do: - Own Entity Compliance: You’ll be the point person for keeping our corporate entities in "Good Standing" across the US and Canada. You’ll handle the reports and state requests entirely on your own. - Protect the Brand: Monitor our intellectual property presence and hunt down infringements. You’ll be responsible for drafting and initiating cease-and-desist workflows. - Investigate & Educate: Act as the first line of defense for complex consumer escalations. You’ll investigate the root cause, pitch strategic solutions, and spearhead compliance training initiatives that elevate our entire workforce. - Drive Product & Process Improvements: Review product and process for compliance. When identifying user friction or compliance risk, you’ll partner directly with our Engineering and Product teams to implement systemic improvements. - Run Tight Audits: Lead our compliance audits across operations. You’ll proactively monitor key risk areas, ensuring our practices don’t just meet baseline regulatory standards, but set the industry benchmark for excellence. - Automate Everything: Use AI and low-code tools to turn manual legal chores into scalable workflows. Your goal is to build systems that do the work for you. Requirements: - Academic Excellence: A Bachelor’s degree from an academically rigorous program with demonstrated high performance. - Driver Mindset: A proven track record of extreme resourcefulness. You are the type of person who finds the answer before asking the question. You have an innate need to close loops. - Product & Tech Savvy: You have an interest in using AI/technology to optimize workflows. You prefer a spreadsheet or an automated tool over a manual checklist. - Impeccable Attention to Detail: You have a "zero-error" mentality when it comes to regulatory filings and compliance audits. You have the organizational rigor to ensure no deadline or cross-functional project ever slips through the cracks. - Thrive in High-Performance Environments: You’re comfortable with ambiguity and operate with a deep sense of urgency. You take full ownership of your output. While we appreciate your interest and application, only applicants under consideration will be contacted. 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 at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

We’d love to hear from you if you like: - Making a big impact on day one with a Forbes Top Startup Employer. - Working at a startup that has traction: $240M in funding and 60x revenue growth in 5 years. - Mentorship from serial entrepreneurs and brilliant leaders who have scaled companies like Amazon, Better, LinkedIn, McKinsey, BCG, Bain - Meritocracy: We promote based on performance, ownership, and results, not tenure. About the Opportunity: We are looking for a highly resourceful and ambitious Operations Analyst to join our lean, fast-paced legal team. This isn't a traditional "administrative" legal role. We are looking for someone with a product-focused mindset who doesn't just follow a process but seeks to automate and scale it. The person who succeeds in this role is a natural driver: someone who owns a project from start to finish, solves complex problems without a manual, and has the grit to thrive in a startup environment. If you are eager to sit at the intersection of law, technology, and AI-driven efficiency, we want to hear from you. What You'll Do: - Own Entity Compliance: You’ll be the point person for keeping our corporate entities in "Good Standing" across the US and Canada. You’ll handle the reports and state requests entirely on your own. - Protect the Brand: Monitor our intellectual property presence and hunt down infringements. You’ll be responsible for drafting and initiating cease-and-desist workflows. - Investigate & Educate: Act as the first line of defense for complex consumer escalations. You’ll investigate the root cause, pitch strategic solutions, and spearhead compliance training initiatives that elevate our entire workforce. - Drive Product & Process Improvements: Review product and process for compliance. When identifying user friction or compliance risk, you’ll partner directly with our Engineering and Product teams to implement systemic improvements. - Run Tight Audits: Lead our compliance audits across operations. You’ll proactively monitor key risk areas, ensuring our practices don’t just meet baseline regulatory standards, but set the industry benchmark for excellence. - Automate Everything: Use AI and low-code tools to turn manual legal chores into scalable workflows. Your goal is to build systems that do the work for you. Requirements: - Academic Excellence: A Bachelor’s degree from an academically rigorous program with demonstrated high performance. - Driver Mindset: A proven track record of extreme resourcefulness. You are the type of person who finds the answer before asking the question. You have an innate need to close loops. - Product & Tech Savvy: You have an interest in using AI/technology to optimize workflows. You prefer a spreadsheet or an automated tool over a manual checklist. - Impeccable Attention to Detail: You have a "zero-error" mentality when it comes to regulatory filings and compliance audits. You have the organizational rigor to ensure no deadline or cross-functional project ever slips through the cracks. - Thrive in High-Performance Environments: You’re comfortable with ambiguity and operate with a deep sense of urgency. You take full ownership of your output. While we appreciate your interest and application, only applicants under consideration will be contacted. 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 at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.