Head of Scaled Customer Success & Retention

<div class="content-intro"><p>At <strong>AutoDS</strong>, recently acquired by Fiverr, we're revolutionizing the eCommerce world by providing innovative tools that empower online sellers globally. 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!</p></div><p>We are seeking an execution-driven, data-savvy <strong>Head of Scaled Customer Success & Retention</strong> to lead the post-onboarding revenue and retention engine within our Customer Experience department.</p> <p>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.</p> <p>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.</p> <h4><strong>Key Responsibilities</strong></h4> <ul> <li><strong>Team Leadership & People Management:</strong> Lead, mentor, and establish operational cadences for a team of 5 direct reports</li> <li><strong>Business-User Growth & Retention:</strong> 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.</li> <li><strong>Automated Failed-Payment Recovery (Dunning):</strong> 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.</li> <li><strong>Reputation & Social Proof Programs:</strong> Oversee the strategy for generating high-quality reviews across key platforms to drive organic acquisition and brand trust.</li> <li><strong>AI-Driven Journey Optimization:</strong> Serve as the primary revenue owner in CX for AI automation initiatives. Ensure maximum revenue conversion rather than just deflecting volume.</li> <li><strong>Trial-to-Paid Conversion:</strong> Partner with Product and Growth teams to eliminate friction points during the customer lifecycle to increase conversion from trial to paid subscriptions.</li> </ul> <h4><strong>Requirements</strong></h4> <p><strong>Must-Haves:</strong></p> <ul> <li>4+ years of professional experience in Customer Success, Account Management, or Post-Sale Revenue roles within SaaS or high-velocity tech platforms.</li> <li>At least 2 years of hands-on experience designing or operating within <strong>Digital CS, Scaled CS, or Tech-Touch</strong> customer success models.</li> <li>3+ years of direct people management or proven team leadership experience.</li> <li>Demonstrated track record of building automated lifecycle communications and customer engagement journeys (e.g., via Intercom, automated email workflows, or in-app triggers).</li> <li>Commercial mindset: comfortable owning revenue and retention metrics (Net Retention Rate, recovered revenue, churn cohorts, trial-to-paid conversion) and presenting results to leadership.</li> <li>Data literacy: proficient in translating user behavioral analytics into actionable retention an