Head of Customer Success

Head of Customer Success

Team: Customer Success & Implementation

Reports to: CEO

About XILO

XILO is a fast-growing Vertical AI company transforming how insurance brokers, banks, and credit unions automate their operations. We provide a modern workflow automation platform that powers quoting, marketing, and sales for the insurance industry. Backed by Altos Ventures ($10B AUM) and other top-tier investors, XILO is entering a rapid scale phase post-Series A. Our mission is to set the standard for product and customer experience in the insurance industry.

We live by our values: Fast, Accountability, Customer-Centric, Trust, and Standing Out (FACTS), and we’re building a high-performing team that reflects them.

About the Role

We’re looking for a Head of Customer Success to scale and mature our post-sales organization, spanning implementation, support, and account management. This leader’s first and most critical mission will be to perfect our product delivery experience, ensuring implementations run with the precision, consistency, and polish of a Michelin star restaurant service. Once delivery excellence is achieved, they will evolve the organization’s focus toward high-efficiency post-live operations and ultimately establish a commercial success motion that drives customer expansion and upsell.

The ideal candidate has scaled a customer success function within a B2B vertical SaaS company serving mid-market clients ($20k–$60k ACVs, 50 new accounts per month). They thrive in fast-paced environments, are data-driven, and excel at balancing operational rigor with commercial instincts.

Key Responsibilities

• Scale and operationalize Customer Success, Implementation, and Support to handle growing mid-market volume efficiently.
• Coach and develop a team of 7–10 managers and ICs; foster a culture of accountability, learning, and performance.
• Partner cross-functionally with Sales, Product, and Partnerships to ensure seamless customer transitions and scalable implementations.
• Optimize onboarding by reducing time-to-live and increasing customer satisfaction (CSAT) and adoption metrics.
• Build expansion motion post-onboarding to identify upsell/cross-sell opportunities within existing accounts.
• Implement data-driven operations using Salesforce (or similar) to track retention, health scores, and churn signals.
• Drive retention metrics: achieve 90% gross and 120% net revenue retention.
• Attract, hire, and retain high-caliber CS and Implementation talent as the team scales.

Who You Are

• 8–12 years of Customer Success or Post-Sales leadership experience in B2B SaaS, ideally Vertical SaaS or workflow automation products.
• Experience scaling (not just building) a CS function during Series B–D growth.
• Proven track record of improving post-implementation retention and expansion metrics.
• Experience managing technical, implementation-heavy products that require customer configuration or integration.
• Comfortable working across partnership-driven implementations with complex customer ecosystems.
• Strong people leader with experience managing managers and teams of 7–10 direct reports within orgs of 50 .
• Skilled operator: able to run CS operations through data, systems, and scalable processes.
• Commercially minded: understands how to align post-sales experience with upsell and revenue outcomes.
• Hands-on and player-coach mentality; thrives in a high-growth, dynamic environment.
• Experience in Series B–D stage companies (not late-stage or public).

Bonus Points For

• Experience in insurance technology or other regulated vertical SaaS industries.
• Experience working with AI-driven or workflow automation products.

Why Join XILO

• Be a founding post-Series A leader shaping how XILO scales customer success for the insurance industry.
• Own retention and expansion outcomes that directly drive company growth.
• Work alongside a visionary team and top-tier investors.
• Competitive total rewards package with strong equity upside.
• A culture that values ownership, growth, and customer obsession.