Software Engineer, AI

Who We Are:

At Sixfold, we’re building the AI platform that transforms how insurers evaluate and price risk. Not just another tool that generates summaries or flags issues—we're creating AI agents that actually understand risk the way veteran underwriters do. Our platform is processing billions in premium for some of the world's largest carriers, and we're just getting started.

The technical challenges are wild. We're teaching AI to understand that a bakery in Florida faces different risks than one in Montana. To know when a manufacturing company's pivot from toys to medical devices fundamentally changes their risk profile. To make million-dollar decisions with the same intuition as someone who's been underwriting for 20 years.

What makes Sixfold special isn't just the technology—it's that we're building it with people who deeply understand insurance. Our team includes folks who've built and scaled carriers, researchers who've pushed the boundaries of AI, and engineers who just love solving seemingly impossible problems.

We're still early, but the impact is already real. If you want to build AI that matters—that affects real businesses, real people, and billions in economic activity—Sixfold is where you should be. We're not just digitizing insurance. We're reimagining what it can be.

Who You Are:

• A smart self-starter: You have a bias for action. You orient yourself around solutions and outcomes and don’t wait for others to tell you what to do. But you also understand how to build alignment and conviction for a decision that can’t be taken back easily.
• A force multiplier: You look for ways to magnify your impact and your team’s. When you find a productivity hack, you share it with your teammates and build a tool to make it easier. You document knowledge for the benefit of future teammates. And you lean into AI and automation to improve your productivity.
• An empathetic communicator: You communicate nuanced ideas clearly, whether you're explaining technical decisions in writing or brainstorming in real time. In disagreements, you engage thoughtfully with other perspectives and compromise when needed.
• A learner: You thrive on learning new things. You can name your favorite sources of what’s new in tech and AI, and you’re excited to tell us about your latest hack or discovery.

What You’ll Do:

As a software engineer at Sixfold, you will:

• Build and deliver quality software. You will write, test, and deploy code across our AI pipeline using Python and a variety of generative AI and other machine learning tools & techniques. You'll work with large language models, fine-tune prompts, design evaluation metrics, and implement responsible AI practices. You’ll work on team-level projects, applying engineering best practices and contributing to the team’s technical decision-making.
• Grow as a full-stack developer. You'll have opportunities to build features end-to-end by expanding your skills with Ruby on Rails and React TypeScript. You'll collaborate with our product engineers to understand our tech stack and how AI capabilities integrate with our web app and APIs.
• Collaborate with cross-functional partners. Our teams include product managers, designers, and engineers working together to accomplish shared goals. You will collaborate with these partners, beginning with problem discovery through solution design and delivery. We work in two-week cycles and release to production at least once a week.
• Own your software through its entire lifecycle. In addition to shipping code, you will assess our most pressing product and engineering problems, identify and design solutions, write technical specs, and scope and break down projects. You will also spend approximately one week per quarter on call, serving as the first line of defense against service outages and critical bugs. If you don’t have experience with all of this yet, don’t worry - we’ll teach you!

Qualifications:

• You have 3+ years of professional software engineering experience.
• You are familiar with Python and FastAPI and know their patterns well enough to build features and APIs without significant learning time. Extra credit if you have experience with Pydantic, Notebooks, or Streamlit.
• You have experience building Retrieval-Augmented Generation (RAG) systems using vector databases (e.g., Weaviate, Pinecone, FAISS, or pgvector) and large language models (LLMs). You understand embedding generation, chunking strategies, and retrieval optimization to improve response accuracy and performance. Extra credit if you have experience fine-tuning or orchestrating LLM workflows.
• You want to work in an early-stage, fast-growth tech company. You are comfortable with ambiguity and change. You can own problems and proactively devise solutions, not just wait for somebody to feed you tasks to execute.
• You love communication, collaboration, and execution. You value meaningful commit messages and pull request descriptions and prefer to merge your PRs within a day or two. You appreciate healthy engineering debates but know how to make pragmatic decisions. You take feedback well and are candid with the feedback you give.

Additional Information:

• Expected full-time salary range between $100,000 to $195,000 + equity + benefits.
• Advertised and actual salary ranges may differ by geographic area, work experience, education, and/or skill level.
• This position does not include visa sponsorship. Candidates must be authorized to work in the United States without requiring employer sponsorship.

Our Commitment:

We foster 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.