Forward Deployed Engineer

Remote · Full Time · Travel Required

Insurance underwriting runs on human judgment, manual workflows, and knowledge locked in someone's head. It breaks when that person leaves and doesn't scale when the book doubles.

Sixfold is building AI agents that understand risk the way a 20-year veteran underwriter does. We build systems that make real decisions on billions in premium for some of the world's largest carriers. AI is the product and the workflow.

The Forward Deployed Engineer sits at the edge of what we've built and what our customers need, making AI agents deliver in production. You'll be the senior technical partner on the ground with customers running joint architecture sessions, shipping integrations into their tech stack, and turning recurring patterns into platform capabilities.

This is a senior role for someone who lives and breathes AI tools. If your default workflow is Claude Code or Codex, you orchestrate parallel agents to ship feature work, enjoy spec driven development, and understand evals, tool use, and context engineering, then this role was created for you.

Who We Are:

🏔 Product: Sixfold is the AI brain for underwriting. Our platform handles submissions at scale, assessing risk against appetite, surfacing cited insights, and deploying AI agents to handle research, referrals, and triage so underwriters can focus on building profitable portfolios.

💪 Team: A focused team of insurance operators, AI researchers, and engineers who love hard problems. We're pushing the boundaries of AI adoption across every function, from how we build, to how we sell and to how we support customers. We ship fast and stay close.

📈 Traction: Processing billions in premium for some of the world's largest carriers. We know AI. We know underwriting. We're building what comes next.

About the Role:

You'll be Sixfold's first dedicated Forward Deployed Engineer, anchored to our newest product line and its customers. As we scale, you'll grow into the lead FDE role across Sixfold's product portfolio.

In this role, you will:

Own the technical relationship with a portfolio of customers: joint architecture sessions, integration design, production debugging, and more.
Plug our product into each customer's ecosystem: third-party data integrations, product customizations, and the deep integration work that embeds Sixfold in their underwriting stack.
Ship the work yourself, leveraging agentic engineering best practices.
Surface trends and patterns from customer work and partner with product engineering to land them in the roadmap.
Translate fluently between audiences: from "what does this mean for our renewal" with a Customer Success Manager, to "what's the right primitive here" with a product engineer, in the same afternoon.
Travel to customer sites in the US when the work calls for it.
Help shape the FDE function itself: the operating model, the hiring bar, the success measures. You'll be a primary voice in what FDE at Sixfold becomes.

What Success Looks Like:

Within 30 days: You’re familiar with the domain of an underwriter. You understand where their bottlenecks are, the pain points they feel day-to-day, and how Sixfold fits into their workflow. You’re comfortable in the codebase of our products and have shipped code to production.

Within 60 days: You're DRI on a customer engagement, working with checkpoints rather than oversight. You're shipping integration and customization work and running joint sessions with customer tech teams. You've spotted at least one recurring pattern and partnered with PM to land it in the roadmap. You're baselining your own turnaround time and are starting to see where the leverage is.

Within 90 days: You're running your customer portfolio, making execution calls (mitigate, fix, roadmap) on your own judgment, surfacing tradeoffs, escalating when something warrants it. You're shipping product capability that compounds across customers. You're materially shaping how FDE operates at Sixfold, bringing concrete proposals on the operating model, intake, and success measures.

About You:

Senior level engineer with significant production experience shipping non-trivial systems end-to-end. You've owned things, not just contributed to them.
Agentic coding is your default workflow. You ship real feature work through Claude Code or Codex, orchestrate parallel agents, design specs and prompts as a primary craft, and have strong instincts around evals, tool use, and context engineering. You can show us work you've done this way.
Strong project management instincts. You can hold multiple customer engagements, internal threads, and product bets in flight at once without dropping balls or letting urgency from one quietly tax the others. You know when to push, when to park, and when to escalate.
Clear, consistent communicator. Stakeholders never have to chase you for status. You write clearly, set expectations early, and update proactively across customers, CS, PMs, engineers, and leadership.
You switch altitudes cleanly. High-level with stakeholders, in the weeds with engineers, designers, and PMs — neither end feels like a stretch.
You're comfortable being early. This role doesn't have a playbook yet. You'll help write it.
Deep empathy for the user. You hear what a customer is asking for and what they actually need. You sit with use cases until you understand them, rather than rushing to the most obvious build.
Bias toward leverage over heroics. When you see the same problem twice, you reach for a platform move, not another bespoke patch.
Insurance, insurtech, or enterprise B2B background is a plus but not required.

Compensation:

Expected salary: $175,000–$225,000 + equity + benefits. Advertised and actual salary ranges might differ by geographic area, work experience, education and/or skill level.
Comprehensive benefits, 401(k) with employer match, parental leave, unlimited PTO, and your birthday off!
This position does not include visa sponsorship

Moments We're Proud Of:

Sixfold fosters an environment that welcomes professionals with a diversity of backgrounds and ideas. We value passionate professionals who bring creativity, determination, and a commitment to our mission. At Sixfold, every team member plays a crucial role, with opportunities to make meaningful and visible contributions to our success.

We believe in empowering our employees through continuous growth, learning, and a proactive problem-solving approach. Our comprehensive compensation package includes competitive salaries, equity opportunities, and robust benefits, all within a supportive and inclusive workplace culture. If you're driven to make a significant impact alongside exceptional colleagues, we want to hear from you.

We are committed to accessibility and provide reasonable accommodations for qualified individuals with disabilities and disabled veterans throughout our recruitment process. If you have any difficulty using our online system and you need accommodation due to a disability, please reach out to us directly at (646) 847-8824.

Sixfold does not accept unsolicited agency resumes and is not responsible for any fees related to unsolicited resumes.

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Forward Deployed Engineer

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