Job Description

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 .

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