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 them, and drive decisions from them.
• Technical curiosity. You do not need to code, but you should be comfortable discussing integrations, APIs, workflows, and AI concepts with customers and engineers.
• A bias for ownership and speed, with the ability to thrive in ambiguity at a fast-growing startup.
• Nice to Have
• Experience with AI, automation, or voice products.
• Familiarity with TMS, WMS, or CRM systems.
• Spanish, Portuguese, or another language, given our LatAm and international customer base.
• Prior experience at an early-stage or high-growth startup, ideally through a Series A to C stage.
• Why HappyRobot

Why Join Us

Join a world-class team of engineers and builders.

Backed by top investors including a16z, Y Combinator, Base10, Prysm Capital, and Eurazeo.

Have ownership and autonomy of projects and are encouraged to ship.

Comprehensive benefits including healthcare, dental, and vision coverage.

Competitive salary + equity in a high-growth startup.

Our Operating Principles

Extreme Ownership

We take full responsibility for our work, outcomes, and team success. No excuses, no blame-shifting. If something needs fixing, we own it and make it better. This means stepping up, even when it is not “your job.” If a ball is dropped, we pick it up. If a process is broken, we redesign it. We do not wait for someone else to solve it. We lead with accountability and expect the same from those around us.

Craftsmanship

Putting care and intention into every task, striving for excellence, and taking deep ownership of the quality and outcome of your work. Craftsmanship means never settling for “just fine.” We sweat the details because details compound. We aim to deliver jaw-dropping outcomes by being curious, meticulous, and proud of what we build, even when nobody is watching.

We are “majos”

Be friendly and have fun with your coworkers. Always be genuine and honest, but kind. “Majo” is our way of saying: be a good human. Be approachable, helpful, and warm. We give feedback with kindness, challenge each other with respect, and celebrate wins together without ego.

Urgency with Focus

Create the highest impact in the shortest amount of time. Move fast, but in the right direction. We prioritize ruthlessly, act decisively, and stay aligned. We are running a high-speed marathon, not a sprint with no strategy.

Talent Density and Meritocracy

Hire only people who can raise the average; exceptional performance is the passing grade. Ability trumps seniority. We reward contribution, not titles or tenure.

First-Principles Thinking

Strip a problem to physics-level facts, ignore industry dogma, and rebuild the solution from scratch. We do not copy-paste solutions.