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.

The Role

We are hiring a Principal Underwriter, AI Strategy & Systems to serve as the domain expert behind our AI underwriting platform. This is not a traditional underwriting desk. You are the architect of how our AI thinks about risk.

As a Principal, you will own the intellectual framework that shapes our platform's underwriting judgment. You will define what "good" looks like across commercial lines, build the systems that measure it, and create the ground truth that engineers and product teams use to train, evaluate, and improve our models. You will work directly alongside AI engineers and product teams to translate decades of underwriting judgment into structured, scalable knowledge, and you will own the feedback loop when the system gets it wrong.

What You Will Do

Evaluation Framework Design

• Own the design of evaluation criteria that measure underwriting competency across specific dimensions (risk selection, coverage analysis, pricing adequacy, hazard identification, and loss history interpretation)
• Define what "correct" looks like for AI-generated underwriting output and establish the scoring methodology to measure it
• Develop evaluation frameworks aligned with professional underwriting competency standards and carrier best practices

Knowledge Base Development, Validation & AI Benchmarking

• Serve as the primary architect and validator of our underwriting knowledge base across commercial P&C lines (Commercial Property, General Liability, Workers Comp, Commercial Auto, Umbrella, Professional Liability, Inland Marine, Cyber Liability)
• Author and own underwriting guidelines, risk appetite frameworks, and line-of-business knowledge documents that define how the platform thinks
• Identify gaps, errors, and ambiguities in AI-generated underwriting analysis and provide expert corrections with clear, structured rationale
• Ensure knowledge base content reflects current market practices, regulatory requirements, and carrier appetite standards
• Annotate commercial insurance submissions, loss runs, schedules of values, and supplemental applications with expert underwriting judgment
• Develop and own annotation guidelines that capture how experienced underwriters evaluate risk across lines of business and industries
• Build and maintain gold-standard evaluation datasets that serve as ground truth for AI model benchmarking and improvement

Who You Are

Required

• 10+ years of commercial lines underwriting experience across multiple lines of business (minimum 3 of the following: Property, GL, WC, Commercial Auto, Umbrella, Professional Liability, Inland Marine, Cyber)
• Demonstrated multi-industry experience underwriting accounts across diverse NAICS classifications (manufacturing, construction, hospitality, professional services, technology, etc.)
• CPCU designation or equivalent professional credentials (CIC, AU, ARM, AINS)
• Experience in underwriting management, supervision, or mentorship, with a track record of developing underwriting capabilities in others
• Exceptional analytical writing skills. You can articulate complex underwriting rationale clearly, consistently, and in ways non-underwriters can understand
• Expert in ACORD standards and commercial insurance data structures
• Comfortable working in digital tools and structured data formats. You don't need to code, but you operate well beyond email and spreadsheets

Preferred

• Experience as an underwriting trainer, instructor, or curriculum developer (carrier training programs, industry education such as The Institutes or Risk & Insurance Education Alliance)
• Familiarity with AI/ML concepts in insurance, particularly how models are trained, evaluated, and improved through human feedback and annotation
• Background in both standard and specialty commercial lines
• Experience with reinsurance concepts and portfolio-level risk analysis

Additional Information:

• Expected full-time salary range between $145,000 to $150,000 + 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.

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.

What You’ll Do:

• Conduct technical product demonstrations. Lead compelling product demos for prospective clients, translating complex technical features into business value propositions. You'll customize presentations to address specific customer pain points and use cases, often handling live Q&A sessions about technical capabilities, integrations, and implementation requirements.
• Collaborate on solution design and proposals. Work closely with the sales team to architect tailored solutions that meet customer technical requirements. You'll participate in RFP responses, create technical specifications, and develop proof-of-concept implementations that demonstrate how our platform addresses the prospect's unique challenges.
• Provide pre-sales technical support. Serve as the primary technical point of contact during the sales cycle, answering detailed technical questions, conducting feasibility assessments, and working with customer IT teams to understand integration requirements, security protocols, and infrastructure needs.
• Support deal progression and closing. Partner with Account Executives to advance opportunities through the sales pipeline by addressing technical objections, facilitating technical evaluation periods, and presenting to technical decision-makers and C-level executives to secure buy-in on the technical aspects of the solution.
• Bridge the gap between sales and implementation by participating in handoff meetings, documenting technical requirements gathered during the sales process, and ensuring smooth transition to the customer success team with comprehensive technical context.

Who You Are:

• A Compelling Communicator. You're equally comfortable presenting to a room of developers and a boardroom of executives. You can adapt your communication style, create engaging technical demonstrations, and articulate complex ROI calculations in ways that resonate with different audiences.
• A Continuous Learner. You stay current with industry trends, emerging technologies, and competitive landscape developments. You're passionate about understanding how new technical capabilities can solve customer problems and aren't intimidated by learning new platforms, APIs, or integration patterns as our product evolves.
• A Wearer of Many Hats. You thrive in a dynamic environment where priorities shift quickly and you're comfortable taking on diverse responsibilities beyond your core role.
• An Enterprise Sales Expert. You bring experience supporting complex enterprise sales cycles, engaging both technical and business stakeholders. You’re skilled at uncovering requirements, designing tailored solutions, and clearly articulating value, you help accelerate deals by building trust across IT and executive levels. You’re comfortable navigating procurement, collaborating closely with Account Executives ensuring technical fit and driving customer confidence. Industry domain expertise is a plus.

Qualifications

• 3+ years of client-facing experience in consultative selling or customer success roles. You're skilled at asking probing questions to uncover technical requirements and business needs, positioning yourself as a strategic partner rather than just a vendor.
• 3-5 years of technical experience in software engineering, solutions architecture, or technical consulting. You excel at translating complex technical concepts into clear business benefits and understand both the technical intricacies of software solutions and the business challenges they solve.
• You have proven experience with product demonstrations and PoCs, with the ability to explain technical concepts effectively to diverse audiences ranging from technical practitioners to C-level executives.
• You thrive in early-stage, fast-growth environments and are comfortable with ambiguity and change. You can own problems end-to-end and proactively devise solutions rather than waiting for tasks to be assigned.
• Gen AI / must use AI to solve problems

Additional Information:

• Expected full-time salary range between $125,000 to $195,000 + OTE + 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.

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.

The Role

We’re looking for a Lead Product Designer to own design for our flagship Property & Casualty underwriting AI product. This role is ideal for a senior, generalist designer who thrives in a highly collaborative environment and enjoys tackling complex problems in enterprise AI software. You’ll partner with PMs, developers, and AI engineers as a peer—shaping an experience that blends agent automation with the nuanced judgment of underwriters, and defining how our agents reason, act, fail, and hand off to humans. This role reports to our Head of Design and is a senior IC position with mentorship responsibilities, with meaningful influence on our design patterns, process, and culture.

What You'll Do

• Own design direction for our P&C underwriting product, from discovery through iteration.
• Design agentic workflows and human-in-the-loop interactions with AI engineers.
• Tinker and build—use agentic coding tools like Claude Code to ship changes and experiment.
• Mentor designers and raise the design bar across your product area.
• Synthesize research into insights that shape roadmap and workflow design.

What We're Looking For

• 7+ years in product design with enterprise software shipped to production.
• AI fluency — you engage on agentic architectures, HITL patterns, and failure modes as a peer.
• Systems-first thinking — you map agent flows and handoff logic before opening Figma, and connect dots across projects.
• Strong facilitator — you can lead a room through a hard decision even when you don't have all the answers.
• Enterprise SaaS / Insurtech experience preferred — complex, data-driven workflows. Even better if you've worked in insurance.

You'll be a great fit if…

• You bring generalist range across the design process, from research to visual design to content.
• You're excited about building at the cutting edge of AI and discovering new UX patterns where best practices haven't been solidified.
• You want to rethink what a good design process looks like in the world of AI agents.
• You follow AI developments and stay hands-on — trying new models and tools to learn what they make possible.

Additional Information:

• Expected full-time salary range between $165,000 to $190,000 + equity + benefits.
• Advertised and actual salary ranges may differ by geographic area, work experience, education, and/or skill level.
• About half the company works in the NYC office 3-4 days a week. This can be a remote role, but applicants need to work no more +/- 3 hours from Eastern time.
• 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.

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.

The Role

We’re looking for a VP, Customer Success to lead and scale Sixfold’s post-sales organization as we enter our next phase of growth. This is a critical leadership role responsible for driving customer outcomes, retention, and expansion across a growing portfolio of enterprise insurance customers.

You will own the end-to-end customer journey—from onboarding and implementation through adoption, value realization, renewal, and expansion. You’ll work closely with Sales, Product, Engineering, and AI teams to ensure our customers achieve measurable underwriting impact and see Sixfold as a long-term strategic partner.

As an executive leader, you will build and scale the Customer Success organization, define operating models and success metrics, and serve as the voice of the customer internally, influencing product strategy and company priorities.

What You’ll Do

• Own customer retention and expansion across all accounts.
• Build, lead, and scale a high-performing Customer Success organization, including CSMs, getting customers live and production support functions as appropriate.
• This is a true player–coach role: you will lead and scale the Customer Success organization while remaining hands-on with key accounts, complex engagements, and strategic customer moments as needed.
• Define and operationalize the customer lifecycle, including onboarding, adoption, health scoring, renewals, and expansion motions.
• Partner closely with Sales on renewals and upsells, ensuring tight alignment across pre- and post-sales.
• Serve as an executive sponsor for key strategic accounts, building trusted relationships with senior insurance leaders.
• Translate customer goals into measurable outcomes tied to underwriting efficiency, loss performance, and submission quality.
• Establish customer success metrics, forecasting, and reporting (e.g., NRR, churn, time-to-value, adoption).
• Act as the primary internal advocate for customers, providing structured feedback to Product and Engineering to inform roadmap priorities.
• Develop scalable playbooks and processes that support enterprise deployments while maintaining a high-touch experience.
• Represent Customer Success in executive planning and help shape Sixfold’s go-to-market strategy as we scale.

Qualifications

• 10+ years of experience in Customer Success, Account Management, or related post-sales leadership roles, with significant experience in enterprise SaaS.
• Proven track record of building and scaling Customer Success teams at high-growth companies, ideally from Series A/B through later stages.
• Experience working with complex, technical products and sophisticated enterprise customers.
• Strong understanding of renewal and expansion motions in long sales-cycle, high-ACV environments.
• Exceptional executive presence and ability to build trust with senior customer stakeholders.
• Data-driven mindset with experience defining success metrics and using them to guide strategy and execution.
• Demonstrated ability to collaborate cross-functionally with Sales, Product, Engineering, and Leadership.
• Experience in insurance, fintech, or regulated industries is a very desired plus, but not required.

Who You Are

• You’re passionate about driving real, measurable customer outcomes—not just usage metrics.
• You enjoy building structure where none exists and scaling teams and processes thoughtfully.
• You thrive in ambiguous, fast-moving environments and can balance strategy with hands-on execution.
• You’re energized by working closely with customers to solve complex business problems.
• You see Customer Success as a strategic growth lever, not a support function.
• You’re excited to help define what world-class Customer Success looks like in an AI-first enterprise company.

Additional Information:

• This is a full-time, hybrid role based in our NYC office.
• Expected full-time salary range between $205,000 to $245,000 + 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.