Head of Customer Success, US (East Coast)

1 month ago
Full-time
Executive
Customer and Technical Support
Booksy

Booksy

Booksy is a cloud-based appointment booking software for beauty professionals, offering automated scheduling, calendar management, payments, and marketing tools. With over 23 million clients worldwide, Booksy is the largest Beauty Booking Marketplace, ...

Diversified Consumer Services
251-1K
Founded 2014
$119M raised

Description

  • Lead the US Customer Success organization, including Onboarding, Retention, and Support teams, and ensure alignment with global CS strategy.
  • Redesign and scale the B2B onboarding journey to reduce time-to-first-value (TTFV) and improve activation and adoption rates.
  • Implement process efficiencies and automation across onboarding workflows to enable scalability and reduce operational friction.
  • Partner with Product, Sales, and Operations to ensure seamless handoffs, improved data flow, and clear accountability across the customer lifecycle.
  • Define, track, and own onboarding and CS performance metrics (activation, adoption, churn within 120 days, NPS, CSAT) and drive continuous improvement through data insights.
  • Lead, mentor, and develop a high-performing CS leadership team and foster a culture of ownership, learning, and customer focus.
  • Collaborate with Global Enablement and Workforce Management to ensure effective resource planning, training, and performance management.
  • Represent the voice of the customer in the US market and contribute insights to influence product roadmap and operational priorities.
  • Manage cost-to-serve and ensure financial efficiency while maintaining high customer satisfaction.

Requirements

  • 8+ years of experience in Customer Success, Onboarding, or Account Management in a fast-paced B2B SaaS or marketplace environment.
  • Proven track record of building or transforming onboarding operations at scale, ideally across multi-geo or hybrid CS models.
  • Strong analytical mindset with experience in KPI ownership, forecasting, and data-driven decision making.
  • Experience implementing automation, tooling, or AI-driven onboarding solutions (examples: Intercom, Salesforce, Userpilot).
  • Excellent leadership skills with experience inspiring teams through change and delivering measurable impact.
  • Exceptional communication and stakeholder management abilities across cross-functional teams.
  • Fully bilingual in English and Spanish.
  • Strategic thinker who thrives in a high-growth, evolving environment.
  • Role based in the United States and requires working in the EST time zone.

Benefits

  • Remote work with $50/month home phone/internet reimbursement.
  • Comprehensive health, dental, and vision coverage with UnitedHealthcare (UHC).
  • Company-paid short-term and long-term disability (STD/LTD) and Basic Life Insurance at 1x salary up to $250,000.
  • FSA/HSA available with Booksy contributions of $1,000 (employee) / $2,000 (employee plus).
  • 401(k) with 50% match up to 8% of contributions paid annually and a 3-year vesting period.
  • PTO: unlimited for exempt employees (with manager approval) and 160 hours/year for non-exempt employees; plus 12 observed holidays.
  • 12 weeks of paid parental leave and access to EAP, voluntary pet insurance, financial wellness tools, employee discounts, and a $50/month Booksy app service credit.

Interested in this position?

Apply directly on the company website

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