Head of Customer Success

About HappyRobot HappyRobot is the infrastructure for enterprises to build and orchestrate AI workforces. Our AI workers don't just communicate through voice and email - they make decisions, take action, and run operations autonomously across entire enterprise systems. Born in Y Combinator (S23) and backed by a16z, Base10, Prysm Capital and Eurazeo with over $200M raised, we power critical operations for global enterprises worldwide. Our platform is battle-tested in the most demanding environments, where AI has real consequences. We started in logistics, built our own voice stack, models, and orchestration layer from the ground up, and are now bringing that infrastructure to every enterprise that runs the real economy. Learn more about our vision in our manifesto. The Role As the Head of Customer Success, you will own the post-sale experience for HappyRobot’s largest and most strategic enterprise customers, and you will build the team and systems that scale it. You will set the vision, structure, and operating rhythm for Customer Success, with direct accountability for adoption, retention, net revenue retention, and expansion across our customer base. This is a player-coach leadership role. In the near term, you will stay close to our top accounts and serve as an executive sponsor in critical customer relationships. Over time, you will hire and develop a team of Customer Success Managers, define the playbooks they run, and partner with Sales, Deployment, Product, and Engineering to make sure every customer sees measurable value from their AI workforce. We are especially interested in leaders with a logistics background who can earn the trust of large, complex organizations and speak the language of their operations teams. What You Will Do Own the Customer Success function and its targets for gross retention, net revenue retention, expansion, and customer health. Serve as the executive sponsor for our largest enterprise accounts, building relationships with operators, VPs, and C-level stakeholders. Hire, onboard, coach, and develop a high-performing team of Customer Success Managers, and define clear career paths and performance standards. Build the Customer Success operating model, including account segmentation, coverage models, health scoring, renewal forecasting, and escalation processes. Create repeatable playbooks for onboarding, adoption, business reviews, risk management, and expansion that scale across regions and customer types. Partner with Sales to identify and close expansion opportunities into new use cases, business units, and geographies, and own the renewal motion. Work closely with Forward Deployed Engineers and Deployment Strategists to ensure smooth handoffs from implementation to ongoing success. Act as the voice of the customer inside HappyRobot, translating feedback and usage patterns into clear input for Product and Engineering. Define and report on Customer Success metrics, and present performance, risks, and strategy to the executive team and board. Select and implement the tools and systems the team needs, such as CRM, health scoring, and customer analytics. What You Bring 10 or more years in Customer Success, Account Management, or a similar customer-facing function at a B2B SaaS or technology company, including 3 or more years leading and scaling a team. Preferred: Hands-on logistics, freight, or supply chain experience (for example at a freight broker, 3PL, carrier, shipper, or logistics technology company), ideally managing large, multi-stakeholder accounts. A proven track record of owning retention, net revenue retention, and expansion targets for enterprise customers. Experience building a Customer Success function from an early stage, including hiring, process design, and tooling. Strong executive presence and the ability to communicate with both operators on the floor and C-level stakeholders. Comfort with data. You can read usage and performance metrics, build a clear narrative around t…

View the full posting and apply