Head of Customer Success

We are hiring our first Head of Customer Success to help us continue delivering the premier barbershop experience for our community. The brand loyalty that we have is born from true love of our product and how we enable those who use it. Users appreciate the care and craftsmanship that goes into each release and how we communicate its value. You’ll need to be a top notch problem solver with an edge - we’re adding ten's of thousands of users every week so you’ll have to learn fast and be quick on your feet.

You'll lead our CS team and curate a level of trust with our users and grow with the company.

• Define and embed a company-wide Customer Success philosophy
• Build and lead the Customer Success team (hiring, training, performance)
• Design the end-to-end customer journey, from onboarding to long-term retention
• Create scalable feedback loops between customers and Product
• Develop customer segmentation and tailored engagement strategies
• Own retention, adoption, satisfaction, and customer health metrics
• Reduce churn by identifying risk early and improving time-to-value
• Partner with Sales to support expansion and upsell opportunities (where appropriate)
• Lead escalation management for high-impact customer issues
• Build CS playbooks, tooling, and processes that scale with rapid growth

• 7–10+ years in Customer Success, Account Management, or related roles
• Experience building or scaling CS teams in SaaS, marketplace, or subscription businesses
• Strong operator mindset: you’ve built processes, not just inherited them
• Comfortable working cross-functionally with Product and Engineering
• Data-informed, but deeply customer-driven
• Able to thrive in ambiguity and rapid growth
• Executive presence with the ability to influence senior leaders
• Genuine passion for barbers, small businesses, and culture
• You’ve booked a haircut on theCut (or will immediately)

• Great medical, dental, and vision insurance options
• 401(k) plan to help save for your future