GM, New Bets (0-1 products)

Jerry; Toronto; Remote; CAD 281,000 - 351,000; Full time

Benefits offered by this job

Health insurance

Dental coverage

Vision coverage

Paid time off

Parental leave

401K matching

Wellness benefits

Equity options

Job summary

Jerry.ai is seeking a General Manager to lead a new business line, reporting to the Cofounder/CEO. You will own the P&L, set the strategy, and be accountable for product development, customer growth, partnerships, and operations.

Depending on the product line, you may manage a small team (1–2 people to start). This is a high-impact role at a late-stage startup with a strong user base, capital, and a high-caliber leadership team.

Qualifications

• 6+ years of experience in venture capital, private equity, or hands-on operating roles in fast-growing startups.
• Bachelor’s degree in any discipline.
• Ability to work in person in our Palo Alto office alongside our CEO and executive team.

Responsibilities

• Own the P&L, set the strategy, and be accountable for product development, customer growth, partnerships, and operations.
• Lead a small team (1–2 people to start) and scale a new product line within a late-stage startup with an existing user base.
• Collaborate with cross-functional partners to drive growth and operational excellence.

Skills

Startup leadership

Venture experience

High growth

Education

Bachelor’s degree

Job description

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. 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 Our next chapter is about accelerating growth, from 5M to 50M customers by 2030. This year alone, we launched 5 new products: home insurance, property tax, motorcycle insurance, car repair shop bids, and roadside assistance, among others within car and home ownership categories currently incubating. Each of these new businesses comes with its own operational complexity, distinct customer pain points, and its own path to scale. We are looking for a General Manager to lead one of these new businesses. Reporting directly to our Cofounder/CEO, you will own the P&L, set the strategy, and be accountable for everything from product development, customer growth, partnerships, and operations. Depending on which product line, you may also lead a small team (1-2 people to start). If you’re looking for an opportunity to build and scale a new business within a late-stage startup with an existing user base, product market fit, capital, traction, and a high caliber team, we’d love to hear from you! Who We Get Excited About

• Owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside your swim lane.
• Insatiable learner: You are constantly seeking to deepen your knowledge, sharpen your skills, and master whatever you’ve set your mind to.
• Tenacious: You are highly resilient. No challenge is too difficult, no issue unsolvable.
• Sense of urgency: You have a strong bias for action and are impatient when progress is stalled.

What You Bring

• 6+ years of experience in venture capital, private equity, or hands-on operating roles in fast-growing startups
• Bachelor’s degree in any discipline
• Ability to work in person in our Palo Alto office alongside our CEO and executive team

Compensation This position offers base salary and stock options. The base salary for this position within the San Francisco Bay Area is $200,000— $250,000 USD, but we can be flexible based on your prior experience and appropriate job levelling. We also offer comprehensive benefits including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with 4% employer matching, and wellness benefits, among others. 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 [e-mail]. 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.