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.

• 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.

Must-Haves:

• 4+ years of professional experience in Customer Success, Account Management, or Post-Sale Revenue roles within SaaS or high-velocity tech platforms.
• At least 2 years of hands-on experience designing or operating within Digital CS, Scaled CS, or Tech-Touch customer success models.
• 3+ years of direct people management or proven team leadership experience.
• Demonstrated track record of building automated lifecycle communications and customer engagement journeys (e.g., via Intercom, automated email workflows, or in-app triggers).
• Commercial mindset: comfortable owning revenue and retention metrics (Net Retention Rate, recovered revenue, churn cohorts, trial-to-paid conversion) and presenting results to leadership.
• Data literacy: proficient in translating user behavioral analytics into actionable retention and growth playbooks.
• Familiarity with engagement, workflow automation, and analytics tools (e.g., Intercom / Intercom Fin, Zapier, Make.com, Mixpanel, Tableau).
• Full professional fluency in English (verbal and written).

Nice-to-Haves:

• Experience from a B2C companies
• Experience in the e-commerce landscape, dropshipping ecosystem, or Shopify platform integrations.
• Background in managing customer advocacy, referral programs, or digital review campaigns.
• Understanding of SaaS payment gateways, subscription billing logic, and automated dunning processes.