GM-in-Training (YC cofounder/CEO-led)

Operations · Palo Alto, California · Remote · FullTime · Senior level

This is a rotational leadership program where a small group of people work directly under the cofounder and CEO on high-impact business problems across product, growth, operations, finance, engineering and data. The posting asks for four or more years in consulting, venture capital, private equity or startups, plus a bachelor's degree in any field. A strong candidate brings ownership, speed, resilience and a habit of learning fast, with the aim of eventually running a business line's profit and loss.

How it fits the AI era

The company is building an AI advisor for cars, homes and other big assets, so AI is part of the product these new businesses are built on. A person in this role would likely use data and AI tools to size markets, test ideas and spot operational bottlenecks faster. Judgment about which problems to chase, trade-offs between business lines, and earning trust from the CEO and teams stay human.

How it builds AI experience

The role offers a close view of how an AI-driven consumer product is shaped across a company that compares insurance from 100+ insurers and also handles maintenance, recalls and refinancing. Working across product, data and engineering would show how AI features move from idea to launch for new lines like home and motorcycle insurance. Candidates can prepare by learning how AI is used in insurance shopping and by trying AI tools on a real business analysis.

Worth showing

• Structured problem solving
• Owning results end to end
• Launching new business lines
• Working with executives

This is our own read, written from the employer's posting and the company's Spotlight. The employer's posting is the source of truth for the role.

About Jerry

A free app that uses AI to shop car insurance across 100+ insurers, per the company, and manage the rest of car ownership, maintenance, recalls and refinancing, in one place.