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Salary: USD 245,000 - 285,000 / annual
Sixfold is building AI agents that transform insurance underwriting by automating risk assessment and decision-making at scale. The company processes billions in premium for major carriers, replacing manual workflows and human judgment bottlenecks with AI systems that understand risk like experienced underwriters.
As VP of Product, you will own the strategic direction of AI-native underwriting and lead the product team to realize it. This is not a management-heavy role—it's a hands-on position where you prototype new ideas yourself before scaling them across the team. You'll set a clear 12-month strategic theme while remaining flexible on tactics, staying current on AI's leading edge, and building the first versions of new concepts through prototypes, demos, and lighthouse customer tests.
Key responsibilities include:
- Defining what AI-native underwriting looks like at Sixfold and maintaining that vision over 12 months
- Building prototypes and working demos yourself to validate ideas before team execution
- Staying informed on AI advancements to inform product direction and industry positioning
- Representing Sixfold's vision of the future of underwriting to customers, partners, and the industry
- Owning the existing product and team, raising operational standards without confusing "working" with "finished"
- Partnering closely with design and engineering to balance prototyping speed with technical quality
Success means developing deep understanding of Sixfold's risk-reasoning AI within three months, moving beyond documentation to forming your own opinions on product edges. By end of Q1, the engineering team should move faster due to improved clarity, not because of management overhead.
You excel at thinking systemically about complex problems, moving fluidly from research to implementation, and designing experiences where best practices don't yet exist. You've shipped products from zero to production and can articulate the business impact (ARR, retention, adoption). You prototype to learn, not to perform. You use AI as a tool to move faster, but retain judgment on what's worth building. You've inherited strong teams before and know when to improve versus replace.
