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.