Head of Customer Success
About The Position
The Head of Customer Success will own the post-sale experience for HappyRobot’s largest and most strategic enterprise customers and build the team and systems to scale Customer Success. The role sets the function’s vision, structure, and operating rhythm, with accountability for adoption, retention, net revenue retention, and expansion across the customer base. This is a player-coach leadership position. Initially, the role will remain close to top accounts and serve as executive sponsor in critical customer relationships. As the function grows, the Head of Customer Success will hire and develop Customer Success Managers, define their playbooks, and partner with Sales, Deployment, Product, and Engineering to ensure customers see measurable value from their AI workforce. HappyRobot is particularly interested in leaders with logistics backgrounds who can earn the trust of complex organizations and understand operations teams.
Requirements
- 10 or more years in Customer Success, Account Management, or a similar customer-facing function at a B2B SaaS or technology company.
- 3 or more years leading and scaling a team.
- 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 ability to communicate with both frontline operators and C-level stakeholders.
- Comfort with data, including interpreting usage and performance metrics, building a clear narrative, and driving decisions from them.
- Technical curiosity and comfort discussing integrations, APIs, workflows, and AI concepts with customers and engineers; coding is not required.
- Ownership mindset and ability to thrive amid ambiguity at a fast-growing startup.
Nice To Haves
- Hands-on logistics, freight, or supply chain experience, ideally managing large, multi-stakeholder accounts.
- Experience with AI, automation, or voice products.
- Familiarity with TMS, WMS, or CRM systems.
- Spanish, Portuguese, or another language, given the LatAm and international customer base.
- Prior experience at an early-stage or high-growth startup, ideally through Series A to C.
Responsibilities
- Own the Customer Success function and its targets for gross retention, net revenue retention, expansion, and customer health.
- Serve as executive sponsor for the largest enterprise accounts and build relationships with operators, VPs, and C-level stakeholders.
- Hire, onboard, coach, and develop Customer Success Managers; define career paths and performance standards.
- Build the Customer Success operating model, including account segmentation, coverage models, health scoring, renewal forecasting, and escalation processes.
- Create scalable playbooks for onboarding, adoption, business reviews, risk management, and expansion across regions and customer types.
- Partner with Sales to identify and close expansion opportunities in new use cases, business units, and geographies, and own the renewal motion.
- Work with Forward Deployed Engineers and Deployment Strategists to ensure smooth handoffs from implementation to ongoing success.
- Represent the voice of the customer internally by translating feedback and usage patterns into input for Product and Engineering.
- Define and report Customer Success metrics, and present performance, risks, and strategy to the executive team and board.
- Select and implement tools and systems for the team, such as CRM, health scoring, and customer analytics.
Benefits
- Comprehensive healthcare, dental, and vision coverage.
- Competitive salary and equity in a high-growth startup.
- Ownership and autonomy of projects, with encouragement to ship.
Stand Out From the Crowd
Upload your resume and get instant feedback on how well it matches this job.
What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
