Head of Customer Success

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

Bonus Points For

Why Join XILO