Senior Product Manager, Agentic AI

Senior • Remote

159,996 - 200,004 USD/yr

Chicago, IL , +4

Why Join

Join a pre-IPO startup with $240M raised, 5M+ customers, and profitability.

Impact: Lead the customer-facing Agentic AI product leveraging LLMs, agents, and internal APIs to create a seamless customer experience. Partner with OpenAI to integrate services into the ChatGPT App and pioneer new model capabilities.

Flat org structure, ambitious goals, and direct reporting to the COO with ownership of a key growth lever.

Why We’re Hiring

The experience of owning major assets like cars and homes is fragmented and outdated. We are building the first app to manage the entire lifecycle.

Our homegrown generative AI infrastructure already automates a significant share of sales and service conversations end-to-end. However, prompts and AI systems are distributed across multiple locations without a unified platform or ownership of future initiatives such as voicebot and computer-use agents. This role will define and lead that roadmap.

How You’ll Make an Impact

Lead end-to-end development of the AI platform and customer experiences from roadmap to rollout.
Design prompt strategies, evaluation frameworks, and guardrails balancing latency, cost, and accuracy.
Establish AI best practices and platform standards across engineering and product teams.
Drive systematic improvements in answer quality, automation rates, and customer satisfaction through experimentation.
Collaborate with OpenAI to deploy next-generation voice models and workflow automation.

Who You Are

Deeply engaged with modern LLM systems and AI technologies.
Comfortable with API design and system architecture discussions.
Data-driven with SQL proficiency for analysis and hypothesis validation.
Pragmatic in managing technical tradeoffs and implementing standards.

Ideal Experience

4+ years in a technical role such as forward deployed engineering or technical product management.
Experience building scalable, production-grade AI products.
Strong interest in LLMs and evolving AI systems.

Compensation & Benefits

Base salary range: $160K - $200K, with potential equity grants.

Comprehensive benefits including health, dental, and vision coverage, paid time off, paid parental leave, 401(k) with employer matching, and wellness benefits.

Jerry

Jerry is a pre-IPO startup in the car ownership industry. They are building an AllCar™ super app that simplifies and automates all aspects of owning a car. Backed by artificial intelligence and machine learning, Jerry provides personalized services for car owners' needs, including insurance, financing, maintenance, and safety. They have a strong focus on innovation and improving their AI-powered app. With over 5 million customers, Jerry is the #1 rated and most downloaded app in their category. The company was founded in 2017 by serial entrepreneurs and has raised over $240 million in financing. Jerry is committed to providing a talent-dense environment for its employees, offering opportunities for learning and career growth. They are dedicated to disrupting the car ownership market and are on a mission to revolutionize how people manage their cars.

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