VP, Customer Success

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.