Customer Success Onboarding Team Leader

Booksy

14h•Remote

About The Position

Working in a rapidly growing, ever-changing scale-up 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 enjoy inventively solving problems with others, helping create clarity when things get confusing, and prioritising your own path within ambiguity, then the chances are that you'll love the opportunities available to grow your career at Booksy. The people you’ll like to work with and things you'll enjoy impacting: As a Customer Success Onboarding Team Leader reporting to the Customer Success Onboarding Manager in our Customer Success team, your purpose will be to lead a team of Onboarding Advisors and serve as the strategic bridge between frontline execution and leadership retention objectives.

Requirements

4-6 years of progressive experience in Customer Success, Onboarding, or Account Management within a SaaS or technology-driven environment.
1-2+ years of formal people management experience leading mid-sized teams.
Demonstrated track record of managing performance through data: QA frameworks, coaching plans, and metric-driven decision-making.
Professional fluency in both English and Spanish (written and spoken), essential for leading a bilingual team and managing escalations.
Expert-level proficiency in Salesforce CRM; working knowledge of CS platforms such as Gainsight, ChurnZero, or equivalent.

Nice To Haves

Retention-First Mindset: You think in NRR, not just activation. You understand that the onboarding conversation sets the retention trajectory.
Multiplier Mentality: You measure your success by your team's output, not your personal output. You get energy from watching others exceed their own expectations.
Structured Ambiguity Navigation: You thrive in scaling environments where processes are still being built. You bring structure without rigidity.
Commercial Acumen: You connect the dots between provider health, expansion signals, and company revenue, and you speak that language fluently in cross-functional conversations.
Coaching Precision: You do not deliver generic feedback. You diagnose root causes, tailor your coaching approach to the individual, and track improvement with clear milestones.

Responsibilities

Coach the Coaches: Design and execute a structured coaching framework for senior advisors, enabling them to independently develop junior team members, freeing you for strategic oversight.
Performance Architecture: Establish clear performance expectations, KPI accountability structures, and career pathing that motivates both high performers and developing talent.
Culture of Excellence: Build and sustain a team environment defined by accountability, continuous learning, and data-driven self-reflection.
KPI Ownership: Drive performance against core metrics: Activation Rate, Reachability, QA Score, Time-to-Value (TTV), and Churn reduction.
Strategic Metric Migration: Lead the team's transition from activation-centric success metrics to NRR and long-term Adoption indicators, aligning frontline activity with company-level retention goals.
Data-Driven Diagnostics: Leverage QA scores, reachability data, and cohort-level performance analytics to identify skill gaps, process breakdowns, and intervention opportunities before they become escalations.
Sales Handoff Integrity: Partner with the Sales team to define and enforce a clean deal standard, ensuring every provider enters onboarding with the right context, expectations, and setup for rapid ROI realization.
Product & Operations Feedback Loop: Systematically surface friction points in the onboarding journey and translate provider-level insights into actionable input for Product and Operations roadmaps.
Bilingual Escalation Leadership: Serve as the senior point of contact for high-complexity provider escalations, conducting resolution conversations fluently in both English and Spanish.

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.
FSA/HSA's available - Booksy contributes $1,000/$2,000 to the HSA 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.