Xenata has been exclusively retained to help a high-growth, VC-backed startup hire its first Head of Customer Success.

A founding role on a team that's reimagining how professionals interact with complex documents using AI.

Our client is building a platform that turns dense, high-stakes contracts into fast, structured, and intelligent outputs. It’s used by top-tier brokerages, legal teams, and specialist firms to make smarter decisions, faster. With strong early traction and a tight-knit founding team, this is an opportunity to help define not just the customer journey, but the company itself.

The Opportunity

We’re looking for a systems-minded builder who can lead everything post-sale: onboarding, training, support, relationship management, and customer advocacy. This role blends strategic ownership with hands-on execution and is perfect for someone who knows how to speak the language of insurance professionals while delivering a world-class SaaS experience.

You’ll work directly with the CEO to create a seamless, empowering journey for expert users who aren’t always tech-savvy, but who do mission-critical work.

🔨 What You’ll Own

Customer Onboarding: Build and run high-touch onboarding experiences tailored to users who live and breathe commercial lines but not AI jargon.
Training & Enablement: Lead product walkthroughs, craft educational content, and host Q&A sessions to drive engagement and confidence.
Relationship Management: Be the face of the company for early users building trust, collecting feedback, and solving problems proactively.
Support Infrastructure: Set up lightweight, scalable tooling (think Intercom, Zendesk), build a help center, and manage ticket workflows.
Customer Programs: Define touchpoints, success plans, feature updates, and engagement strategies that make users feel heard and supported.
Voice of the Customer: Synthesize insights and influence the product roadmap with what you’re learning in the field.
Documentation: Write clear, simple guides for a non-technical audience that demystifies the product and empowers users.
Team Building: Over time, grow and scale the Customer Experience function as the company expands.

✅ You're A Fit If…

You’ve worked in early-stage SaaS (bonus if B2B) and can build from a blank slate.
You have deep insurance experience and know how to “talk shop” with power users.
You’re both empathetic and operational - a systems thinker who thrives on structure and impact.
You're a clear communicator who can translate complex ideas into plain, helpful language.
You operate with a bias for action - you see what’s needed and get it done.
You genuinely care about delivering great experiences, even if you’re not a designer.

🚀 Why This Role Rocks

Founding team: You’ll define the customer journey and strategy.
Massive impact: You’ll be the reason customers love and stick with the product.
Autonomy + ownership: This is your domain - you’ll build the function and grow it.
Mission-driven users: You’re helping professionals who help people recover from disasters. Your work has real-world impact.
AI meets Legaltech: You’ll be at the forefront of modernizing a complex, essential industry.

📊 Success Will Look Like:

Fast onboarding: % of users activated within first week
Strong product adoption: Usage per seat, depth of features used
Healthy accounts: Retention, NPS, CSAT, and engagement
Scalable support: % of tickets resolved via self-service
Customer expansion: Renewals, upsells, seat growth

📩 If you’re ready to build a modern customer experience from scratch. One that supports real users doing critical work then we’d love to hear from you.

Apply here or reach out to the Xenata team directly at Gavin@wearexenata.com

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Head of Customer Success