Head of Customer Success

About HappyRobot

HappyRobot is a platform to build and deploy AI workers that automate communication. See a demo

Our AI workers connect to any system or data source to handle phone calls, email, messages…

We target the logistics industry which relies heavily on communication to book, check on, & pay for freight. Primarily working with freight brokers, 3PLs, freight forwarders, shippers, warehouses, & other supply chain enterprises and tech startups.

We raised a Series A round from a16z and YC and we’re growing very fast.

We're looking for rockstars with a relentless drive, unstoppable energy, and a true passion for building something great—ready to embrace the challenge, push limits, and thrive in a fast-paced, high-intensity environment.

Role Overview

We’re looking for a Head of Customer Success to lead and scale our customer success function. This person will be responsible for driving customer outcomes, building a high-performing team, and shaping the post-sales strategy to ensure retention, growth, and long-term relationship.

What You’ll Do

• Customer Success Strategy – Own the vision, strategy, and execution of the customer success function across the entire lifecycle, from onboarding to renewal and expansion.

• Enterprise Relationship Leadership – Build and maintain strong relationships with key enterprise customers, acting as a trusted advisor and executive sponsor.

• Team Building & Management – Hire, coach, and lead a team of CSMs and support staff, fostering a culture of ownership, collaboration, and accountability.

• Onboarding & Value Delivery – Oversee scalable onboarding and education processes that accelerate time-to-value for customers.

• Churn Prevention & Growth – Drive retention and expansion metrics by identifying risk, standardizing playbooks, and embedding success KPIs across the organization.

• Cross-Functional Alignment – Partner closely with Sales, Product, and Support to align on customer needs and deliver a seamless experience.

• Voice of the Customer – Champion customer feedback to influence product development, company strategy, and operational improvements.

• Systems & Tools – Optimize usage of CS platforms (e.g. Gainsight, Salesforce) and analytics tools to inform decision-making and performance tracking.

Must Have

• 7+ years in Customer Success or related customer-facing roles in high-growth B2B SaaS, including 3+ years in a leadership capacity.

• Proven success managing enterprise customer relationships and navigating complex, multi-stakeholder environments.

• Deep understanding of customer success metrics (retention, expansion, NRR) and how to operationalize them.

• Exceptional leadership, communication, and cross-functional collaboration skills.

• Analytical mindset – comfortable with data, dashboards, and using insights to guide strategy.

• Experience scaling customer success functions, including hiring, process design, and tooling.

• Strong familiarity with CRM and CS platforms (Salesforce, HubSpot, Gainsight, ChurnZero, etc.).

• Founder mindset – you’re energized by ambiguity, take ownership end-to-end, and care deeply about outcomes.

Why join us?

• Opportunity to work at a high-growth AI startup, backed by top investors.

• Fast Growth - Backed by a16z and YC, on track for double-digit ARR.

• Ownership & Autonomy - Take full ownership of projects and ship fast.

• Comprehensive Benefits - Healthcare, dental, vision coverage.

• Top-Tier Compensation - Competitive salary + equity in a high-growth startup.

• Work With the Best - Join a world-class team of engineers and builders.

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’s not “your job.” If a ball is dropped, we pick it up. If a customer is unhappy, we fix it. If a process is broken, we redesign it. We don’t 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. Whether it’s a product feature, an internal doc, or a sales call — we treat it as a reflection of our standards. We aim to deliver jaw-dropping customer experiences by being curious, meticulous, and proud of what we build — even when nobody’s watching.

We are “majos”
Be friendly & have fun with your coworkers. Always be genuine & honest, but kind. “Majo” is our way of saying: be a good human. Be approachable, helpful, and warm. We’re building something ambitious, and it’s easier (and more fun) when we enjoy the ride together. 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 operate with speed because time is our most limited resource. But speed without focus is chaos. We prioritize ruthlessly, act decisively, and stay aligned. We aim for high leverage: the biggest results from the simplest, smartest actions. We’re 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 believe the best teams are built on talent density — every hire should raise the bar. We reward contribution, not titles or tenure. We give ownership to those who earn it, and we all hold each other to a high standard. A-players want to work with other A-players — that’s how we win.

First-Principles Thinking
Strip a problem to physics-level facts, ignore industry dogma, rebuild the solution from scratch. We don’t copy-paste solutions. We go back to basics, ask why things are the way they are, and rebuild from the ground up if needed. This mindset pushes us to innovate, challenge stale assumptions, and move faster than incumbents. It’s how we build what others think is impossible.