Senior Technical Product Manager, AI Engineering & Systems

Why we’re hiring this role

Your car and your home are your most important assets, yet the experience of owning one is fragmented, complicated, and expensive. We are building the first app to manage it all.

We launched car insurance in 2019 and became one of the top three brokers in the country, in part by being early adopters of generative AI. Before off-the-shelf platforms existed, we built our own infrastructure to automate sales and service conversations. Today, that system handles a meaningful share of customer interactions end-to-end, and the underlying technology is entirely homegrown.

As the system evolved, prompts powering the customer-facing chatbot, vehicle photo validation, and back-office automation now live across six separate locations. There is no single source of truth, no unified platform, and no clear owner of future AI bets such as voicebot, computer use, and consumer AI applications. This role owns that challenge.

How you’ll make an impact

Your scope covers two layers: maintaining the current AI platform while driving architectural decisions that determine its future state.

In the first few months, you will learn the prompt engineering workflow by writing and updating prompts, understanding how various tech stacks (e.g., Propelix, Botly, CRM, GitHub, and Replit) interact, and identifying bottlenecks. After that, you will own the platform strategy:

• Prompt consolidation: Define and execute the strategy to migrate prompts from six locations to a unified platform, aligning engineering, data, operations, and other teams.
• Chatbot prioritization: Own the technical prioritization queue and keep the team coordinated without unnecessary process overhead.
• Emerging technology decisions: Track advancements in voicebot and computer use, determine when to invest, own the OpenAI relationship, and manage presence in the ChatGPT store. Influence AI investment decisions with a clear point of view.

Who you are

• Technologist: Deep interest in AI, actively following new model releases and building custom workflows.
• Systems Thinker: Comfortable discussing API design and system architecture and translating complex concepts for varied audiences.
• Experimenter: Continuously exploring new AI capabilities.
• Data-Driven: Proficient in SQL and comfortable analyzing data to validate hypotheses.
• Pragmatic: Able to navigate technical tradeoffs and implement AI platform standards.

Ideal experience

• 4+ years in a technical role such as forward deployed engineering or technical product management in a fast-paced startup.
• Passion and curiosity for AI systems including modern LLMs.
• Proven track record of turning complex strategic ideas into scalable, production-grade products.

Compensation and Benefits

The starting pay range for this role is $160K - $200K, determined by skills, experience, qualifications, work location, and market conditions. Compensation may include equity grants.

Benefits for regular employees include health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits. Equity opportunities may also be part of the total rewards package.