SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 140,000 - 170,000 / annual
WithCoverage is an AI-powered insurance brokerage that replaces traditional risk management with modern technology. Founded by JD Ross (Opendoor co-founder) and Max Brenner (Bain, Compound), the company has raised over $50M from Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners. WithCoverage serves hundreds of high-growth companies including GoPuff, Eight Sleep, Bombas, and Blank Street Coffee, operating across consumer brands, hospitality, construction, advanced manufacturing, and defense sectors.
You will be a customer-facing engineer on the Growth team, building AI-powered tools and workflows while partnering directly with prospects and internal teams. The role blends hands-on software development with client engagement—roughly half your week involves prospect conversations and email threads, the other half involves coding and building.
Key responsibilities:
- Own engineering execution on defined projects: build AI-powered tools, applications, scripts, and integrations; make technical decisions; and handle debugging, testing, deployment, and iteration.
- Build AI workflows that work in practice: connect LLMs, APIs, and business data to solve concrete workflow problems; evaluate outputs against real examples; handle errors and edge cases; improve reliability as people use what you build.
- Participate in prospect conversations and email threads to answer technical questions, demonstrate useful applications of AI, and help Sales move deals forward.
- Teach nontechnical operators in plain language: walk them through tools, demonstrate approaches using relevant examples, help them understand how to use AI effectively.
- Understand prospect workflows well enough to give sound technical guidance; when follow-up work is needed, build prototypes, scripts, or lightweight tools using relevant sample data.
- Keep work useful and maintainable: document what you build, reuse components, communicate technical constraints and tradeoffs to Product and Core Engineering.
This is an in-office role based at NYC HQ, as the position works daily across Marketing, Sales, Revenue Ops, and client-facing executives.
Requirements:
- 4+ years of technical experience, ideally including time in an AI or analytics practice at a consulting firm (QuantumBlack, BCG X, Bain Vector, Accenture, or similar) or in a forward-deployed / solutions engineering role.
- You have built AI-powered things that real people used: prompt engineering, retrieval, agents, evals. It doesn't need to have been at massive scale, but it needs to have been real.
- You can explain how an LLM works to someone who has never written code, and they leave feeling capable rather than lectured to. This is described as the single most important qualification.
- Genuinely strong client instincts: you can read a room, handle a skeptical executive, tell someone their idea won't work without losing them, and know when to stop talking.
- You want to be on calls and in rooms. This is a people-facing job that happens to require an engineer.
