Head of Customer Success, US (Florida)

Your Purpose:

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.

Your team:
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.

What you will do:

• 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.

Please note that while we are a remote-first company, this role will be based in Florida.

Salary range for this position is $130,000 - $150,000 + bonus.

Requirements

What you will bring to the table:

• 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.

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.

A bit about Booksy:

A career at Booksy means you're part of a global team focused on helping people around the world feel great about themselves, every day. From empowering entrepreneurs to build successful businesses, to supporting their customers to arrange 'me time' moments, we're in the business of helping people thrive and feel fantastic.

Working in a rapidly growing and evolving company comes with its own set of opportunities and challenges. If you prefer a stable environment, with clear processes and structures then, we've got to be honest, you won't always find that here. However, if you're a driven self-starter, with initiative and the motivation to grow your career in an environment that's rapidly changing as we scale-up globally, then the chances are that you'll love it at Booksy.

Our Diversity and Inclusion Commitment:

We work in a highly creative and diverse industry so it goes without saying that we strive to create an inclusive environment for all. We welcome people from all backgrounds and are committed to fair consideration in our hiring process. If you have any accessibility needs or require reasonable adjustments during the interview process, please contact us at belonging@booksy.com, so we can best support you.

How AI helps us find great people

Think of our AI tool as a really smart assistant for our recruitment team. Its job? To help us move faster, stay consistent, and make sure no great candidates are overlooked.Every application goes through the same AI review to help us spot skills that match the role - but don’t worry, AI never makes the decisions. Real people do. Our recruiters and hiring managers handle every final call. And we regularly review how the tool is used to keep things fair, ethical, and compliant with data protection laws. Curious about how it works? You can always ask how AI was used in your application - it won’t affect your chances in any way. If you have questions, just drop us a note - we’re happy to explain more.