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Jerry

Head of Marketplace Automation & Growth

Jerry, Chicago, Illinois, United States, 60290

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Position Head of Marketplace Automation & Growth at Jerry.ai

Overview Jerry.ai is a pre‑IPO startup focused on building a super‑app for car ownership, with a $2T market in the U.S. The role helps scale the core insurance business from 5 M to 50 M customers and drive growth to a $10B business.

Responsibilities

Own the systems, strategy, and execution behind Jerry’s quoting engine, automation infrastructure, and carrier performance.

Work cross‑functionally with product, engineering, and analytics to create a seamless user experience and ensure ongoing carrier success.

Drive critical outcomes for our insurance marketplace—loss ratio, retention, and conversion.

Scale the insurance marketplace from 5 M to 50 M customers.

Report directly to the VP of Insurance Operations and shape category‑defining fintech strategy.

Preferred Experience

Bachelor’s degree in a quantitative discipline (Electrical Engineering, Computer Engineering, Industrial Engineering, Operations Research, etc).

7+ years of management consulting experience from a top firm (McKinsey, Bain, BCG).

Track record of hiring and managing high‑performing teams.

Who You Are

You have a structured framework for problem‑solving and live by first principles.

You are comfortable communicating with audiences ranging from technical stakeholders, business partners, to the company’s C‑suite.

You set a very high bar for yourself and for your team, constantly pushing that bar higher in pursuit of excellence.

Benefits Competitive salary, equity opportunities, health, dental, vision coverage, paid time off, paid parental leave, 401(k) plan with employer matching, wellness benefits, and more.

Legal and EEO Statements 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 its job application process. If you need assistance or an accommodation due to a disability, please contact 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.

About Jerry.ai Jerry.ai is America’s first and only super app to radically simplify car ownership. Backed by AI and machine learning, it offers insurance, financing, maintenance and safety services for all car owners. It has more than 5 million customers and is built by serial entrepreneurs with $240 M in funding.

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