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 the entire journey including buy/sell, insurance, maintenance, and repairs.

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.

That head start created leverage but also complexity. Prompts powering the customer-facing chatbot, vehicle photo validation, and back-office automation live across six separate locations with no single source of truth or unified platform. This role owns consolidating and defining the future AI roadmap, including voicebot, computer use, and consumer AI applications.

How you’ll make an impact

Your scope covers maintaining the current AI platform while driving architectural decisions for 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.

• Prompt consolidation: Define and execute the migration strategy from six locations to a unified platform, aligning engineering, data, and operations teams.
• Chatbot prioritization: Own the technical prioritization queue and coordinate execution without adding unnecessary process.
• Emerging technology decisions: Track advancements in voicebot and computer use, determine investment timing, own the OpenAI relationship, and manage presence in the ChatGPT store.

Who you are

• Technologist: Deeply engaged with AI advancements and experienced in building custom workflows.
• Systems Thinker: Comfortable discussing API design and system architecture and translating complex ideas.
• Experimenter: Continuously exploring new AI capabilities.
• Data-Driven: Familiar with SQL and comfortable analyzing data to validate hypotheses.
• Pragmatic: Able to navigate technical tradeoffs and implement AI platform standards.

Ideal experience

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

Compensation and Benefits

The successful candidate’s starting pay will fall within the listed pay range and is determined by skills, experience, qualifications, work location, and market conditions. Compensation may include equity grants.

• Health, dental, and vision coverage
• Paid time off
• Paid parental leave
• 401(K) plan with employer matching
• Wellness benefits
• Equity opportunities may be part of the total rewards package

We are an Equal Employment Opportunity employer and provide reasonable accommodations for individuals with disabilities in the job application process.