Head of Customer Success, US (Florida)

Booksy

2h•$130,000 - $150,000•Remote

About The Position

We’re looking for an experienced and data-driven Head of Customer Success (US) to lead our regional CS function, with a strong focus on driving efficiency and excellence in B2B onboarding. This leader will own the strategy, execution, and continuous improvement of how we onboard, support, and retain our US customers, ensuring every interaction delivers measurable impact and long-term value. You’ll work cross-functionally with Operations, Product, Marketing, and Sales to simplify the customer journey, accelerate time-to-value, and design scalable onboarding frameworks that combine automation, human touch, and strong commercial outcomes. You will join our Customer Success team, a passionate group committed to providing the best service to our customers, and reporting to the VP Customer Success.

Requirements

8+ years of experience in Customer Success, Onboarding, or Account Management within 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 (e.g., Intercom, Salesforce, Userpilot, etc.).
Excellent leadership skills with ability to inspire teams through change and deliver 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.

Responsibilities

Lead the US Customer Success organization, including Onboarding, Retention, and Support teams, ensuring alignment with global CS strategy.
Redesign and scale the B2B onboarding journey, focusing on reducing time-to-first-value (TTFV) and improving 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 from Sales to CS, improving data flow, accountability, and customer experience.
Define and track onboarding 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 with a culture of ownership, learning, and customer obsession.
Collaborate with the Global Enablement and WFM teams to ensure effective resource planning, training, and performance management.
Represent the voice of the customer within the US market, contributing insights to influence product roadmap and operational priorities.
Ensure financial efficiency by managing cost-to-serve while maintaining high customer satisfaction.

Benefits

Remote work with $50/month home phone/internet reimbursement.
Comprehensive health, dental, and vision coverage with UHC.
Company paid STD and LTD, and Basic Life Insurance at 1x salary up to $250,000.
FSA/HSA's available - Booksy contributes $1,000/$2,000 for employee/employee plus.
Accident/Hospital/Critical Illness voluntary plans available.
401k - 50% match up to 8% of contributions paid annually/ 3-year vesting period.
PTO - Exempt employees - unlimited with manager approval. Non-exempt employees - 160 hours/year (does not roll over).
12 Holidays observed.
Parental Leave - 12 weeks of paid leave.
EAP (Employee Assistance Program).
Voluntary Pet Insurance through Fetch.
Financial wellness tools through SoFi and Ladder.
Discounts via Perkspot.
Booksy benefit $50 per month to use on services in our app.