Head of Scaled Customer Success & Retention

We are seeking an execution-driven, data-savvy Head of Scaled Customer Success & Retention to lead the post-onboarding revenue and retention engine within our Customer Experience department.

In this role, you will lead a multidisciplinary team composed of Business Account CSMs, a Failed Payments Recovery Specialist, and a Product Reviews Specialist. You will combine people leadership with tech-touch methodologies, building automated workflows, AI-assisted outreach, and proactive playbooks that maximize customer lifetime value, protect subscription revenue, and scale our operations without linear headcount growth.

This is a builder role designed for a hands-on leader who bridges customer success, marketing mechanics, and lifecycle automation to drive measurable business outcomes.

Key Responsibilities
Team Leadership & People Management: Lead, mentor, and establish operational cadences for a team of 5 direct reports
Business-User Growth & Retention: Lead the proactive CS motion for large accounts. Define account qualification standards, accelerate time-to-value, and build repeatable playbooks that drive product adoption, upsell opportunities, and long-term retention.
Automated Failed-Payment Recovery (Dunning): Own the end-to-end failed payment recovery motion. Transform our existing outreach into a scalable, multi-channel automated system that recaptures involuntary churn at high volume.
Reputation & Social Proof Programs: Oversee the strategy for generating high-quality reviews across key platforms to drive organic acquisition and brand trust.
AI-Driven Journey Optimization: Serve as the primary revenue owner in CX for AI automation initiatives. Ensure maximum revenue conversion rather than just deflecting volume.
Trial-to-Paid Conversion: Partner with Product and Growth teams to eliminate friction points during the customer lifecycle to increase conversion from trial to paid subscriptions.