About us
Jerry.ai is a Series C, YC-backed tech startup with 5M+ customers and $240M in funding. Founded in 2017, product launched in 2019, and achieved profitability in 2024.
Our purpose
Your car, home, and motorcycle aren’t just purchases, they’re the physical embodiment of the life you’ve worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We are building the first AI-powered advisor to manage all your physical assets. We started with your car in 2019, and now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat).
About the role
We focus on impact over volume. The goal of the recruiting team is to make high-quality hires that shape our products, teams, and culture. Our recruiters are embedded partners to the business and work closely with hiring managers to understand their teams. As a senior individual contributor, you’ll run the searches where the bar is highest and a miss costs the most: hard-to-fill roles, competitive markets, and hires with ambiguous scopes. You’ll partner with leaders across the company to define roles before they open, set the bar, and push back when a search needs a different approach.
This role starts as a three-month contract with a direct path to permanent employment. During the contract, you and the team get to see how you work together before making a longer-term commitment.
Why You Will (Or Won’t) Like Working Here
- True ownership: You’ll report to our Director of Talent and own full-cycle recruiting for mid-to-senior and leadership searches. You won’t hand searches off or wait for a committee to approve your outreach. The search is yours.
- A high bar: The wrong hire can set a function back by a year. You’ll be expected to push back on hiring leaders, challenge weak slates, and hold the standard when there’s pressure to fill quickly.
- Ambiguity is the default: Scope and process often change mid-search. If you need a stable req to do your best work, this will frustrate you.
What You’ll Own
- Full-cycle recruiting for mid-to-senior and leadership roles across product, engineering, data science, design and research, business operations, growth, legal, finance, and people operations.
- Working with hiring leaders on search strategies (sourcing, interview design, calibration) built for each role, not copied from a template.
- Reviewing recruiting and interview practices and making improvements that protect quality without wasting the team’s time.
- Mentoring junior recruiters and raising the team’s standard of craft.
Who You Are
- Strategic: You think about how each search affects the team’s overall talent density. You bring hiring leaders a point of view, not just status updates.
- A craftsperson: You care about the candidate experience at every step, from the first message through the offer call, and you notice when something’s off.
- Steady under complexity: You run searches across several functions at once and keep every thread moving when volume spikes.
What You’ll Bring
- 7+ years of full-cycle recruiting, including leadership-level hiring.
- Experience at a fast-growing startup, with a track record in product management, product design, or business operations searches.
- Success in fast-paced environments where quality and speed both matter.
- Bachelor’s degree or equivalent experience.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
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 is building the first AI-powered advisor to manage all your physical assets.
Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.
Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.
We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.
Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.
We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.
We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
Compensation Range: $120K - $160K
