Recruiting Operations Associate (contract to hire)

Boston, Massachusetts · Remote
Full-time
$55K - $75K
Posted Nov 11, 2026

Skills

Communication
Leadership
Logistics
Operations
Recruiting

Job description

You could be a recruiting coordinator anywhere. Why Jerry.ai?

•Join a pre-IPO startup with capital, traction, and runway: We are tackling a $2T market, have $240M in funding, 60X revenue growth, and we’re profitable.

•Launch your career in recruiting. We’re committed to mentoring and promoting high performers into Recruiter or Sourcer roles as you learn our hiring bar and how the business runs.

•You’ll build, not just execute. You’ll run scheduling and logistics, but you’ll also have the autonomy to improve systems, fix bottlenecks, and make the whole team faster and more effective.

Why contract-to-perm?

At Jerry.ai, we move quickly and our hiring bar is high. We treat coordination like white-glove operations rather than just admin support. The contract phase (3 months) is a chance for both sides to see if we’re the right match. You’ll get a front-row seat to our "high ownership, high impact" culture. If you thrive on urgency and precision, the path to a permanent role here is clear.

About the opportunity:

You will be the operational backbone of our recruiting engine, owning the logistics and making sure every candidate experiences a seamless, high-touch process end to end.

We’re looking for a high-velocity operator who doesn’t just execute tasks, but anticipates what’s next, removes friction before it appears, and helps the recruiting team move faster, smarter, and more effectively. You’ll act as a true force multiplier for our recruiting engine, your work will directly shape our ability to attract and hire top talent at Jerry.ai.

How you will make an impact:

•Provide "white-glove" service to candidates by sending personalized pre-interview info and managing LinkedIn outreach

•Manage the lifecycle of take-home assignments, maintain candidate profiles in Ashby ATS, and ensure all candidate documents are accessible to those who need them

•Manage recruiter calendars with precision, rearranging interviews on the fly to prioritize high-impact candidates and maximize our daily capacity

•Act as the point person for leadership’s urgent recruiting needs, whether it's updating compensation bands, posting new job reqs, or coordinating the training/shadowing of new interviewers

Who you are:

•You can’t stand inefficiency: You’re always spotting ways to automate, streamline, and level-up how work gets done, and you enjoy turning messy processes into clean, scalable systems.

•You have an intense sense of urgency: You don't wait for things to happen, you make them happen. You move quickly, close loops fast, and thrive in environments where priorities shift and speed matters.

•Your attention to detail is impeccable: You catch the small things that others miss. Your written communication is clear, polished and professional, and you keep processes tight so nothing slips.

•You are a proactive problem solver: You’re calm under pressure, and comfortable navigating ambiguity. You can handle high-stakes, time-sensitive requests from leadership without losing focus or pace.

Ideal profile:

•Prior experience in a fast-growth startup or a high-volume agency environment is strongly preferred

•Bachelor’s degree

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 http://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 recruiting@getjerry.com

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.