As a fast-growing company, we’re looking for talented individuals who are passionate about technology, eCommerce, and making a real impact. If you're ready to join a dynamic team and thrive in a collaborative, fast-paced environment, we’d love to hear from you!
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.
Requirements
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.
Ready to take your career to the next level with AutoDS? Join us and be part of a global team that’s driving the future of eCommerce innovation. Apply today and help us create cutting-edge solutions for online sellers worldwide!
