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 str