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Director, Business Operations & Strategy; Marketplace

Job in Boston, Suffolk County, Massachusetts, 02298, USA
Listing for: Jerry
Full Time position
Listed on 2026-01-16
Job specializations:
  • Software Development
    AI Engineer, Data Science Manager
Job Description & How to Apply Below
Position: Director, Business Operations & Strategy (Marketplace Growth)

Director, Business Operations & Strategy (Marketplace Growth)

  • Join a pre‑IPO startup with capital, traction and runway ($240M funded | 60X revenue growth in 5 years | $2T market size).
  • Work closely with brilliant leaders and teammates from companies like McKinsey, BCG, Bain, Nvidia, Lemonade, GEICO, Amazon, etc.
  • Disrupt a massive market and help take Jerry.ai to a $10B business in the next few years.
  • Be immersed in a talent‑dense environment and accelerate your career growth.
About The Opportunity

Jerry.ai is looking for a Director, Business Operations & Strategy (Marketplace Growth) to help scale our core insurance business. After achieving profitability in early 2024, we aim to grow from 5M to 50M customers and become a $10B business. In this high‑visibility role, you will report directly to the VP of Insurance Operations and own the systems, strategy, and execution behind Jerry’s quoting Cascades, automation infrastructure, and carrier performance.

Working cross‑functionally with product, engineering, and analytics, you will create a seamless user experience and ensure ongoing carrier success to drive critical outcomes for our insurance marketplace (loss ratio, retention, and conversion). This is a unique opportunity to shape the strategy of Enumerable fintech at scale.

Jerry.ai is building the first super app to make car ownership affordable and accessible – insurance, buy/sell, registration, loans, safety, repairs, parking, etc – a $2T market in the U.S Yr. Since 2019, we launched loan refinancing, driving insights, repair marketplace, car diagnostics, and a GenAI‑powered chatbot & voicebot. We have over 5M customers, $240M in funding, 60X revenue growth, and an 225‑person team across six countries.

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, Boston Consulting Group).
  • Track record of hiring and managing high‑performing teams.
Who You Are
  • Have a structured framework for problem‑solving and live by first principles.
  • Communicate comfortably with audiences ranging from technical stakeholders, business partners, to the C‑suite.
  • Set a very high bar for yourself and for your team, driving continuous excellence.
Equal Employment Opportunity

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.

Compensation & Benefits

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, 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. From 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. With more than 5 million customers and $240M raised, we’re just getting started.

Seniority level:
Director

Employment type:

Full‑time

Job function:
Management and Manufacturing

Industries:
Software Development

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