Head of Client Success

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Location: Toronto or Vancouver; US/remote considered for exceptional candidates

Reports to: CEO

Team: Client Success Managers, Onboarding/Implementation, Help Desk/Support, Training & Enablement

About Uplifter

Uplifter is a sports-tech SaaS powering memberships, registrations, payments, and compliance for 1,000+ clubs and 200+ federations across North America. We're unifying the experience for clubs and governing bodies—and we're just getting started.

The Role (why this is big)

Own and reimagine the end-to-end client journey. As a member of the leadership team, you'll own your team, budget, and outcomes—and have a real shot to modernize how sports organizations run. You'll build strategy and the operating machine (people, process, tooling) that drives retention, NRR, and delightful client experiences.

What You'll Do

Strategy & Leadership

• Set the Client Success strategy for clubs & federations; define coverage models, playbooks, and operating rhythms.
• Build the org (CSMs, onboarding, support, training); hire, coach, and cross-train to remove single-points-of-failure.
• Own the budget (headcount, tooling, programs) and report outcomes at the exec table.
  
  

Onboarding & Implementation

• Standardize high-velocity club onboarding; project-manage complex federation launches (SOW/BRD/UAT/go/no-go).
• Create repeatable implementation kits and decision gates.
  
  

Support Operations (Zendesk) & SLAs

• Run a high-performing Zendesk help desk with strict SLAs, clear tiering/escalation, QA/coaching, and WFM basics.
• Deliver efficiency gains: SOPs/macros, better triage/routing, shift-left policies, self-serve/KB expansion, ticket deflection.
• Introduce AI in support (agent assist, auto-classification/routing, summarization, knowledge search) and measure impact (FCR, handle time, CSAT).
  
  

Adoption, Health & Renewals

• Build lifecycle programs (admin enablement, QBRs, adoption campaigns); forecast health, renewals, and expansion; partner with Sales on upsell/cross-sell; own GRR/NRR.
  
  

Voice of Customer & Product

• Stand up a tight VOC loop to Product/Engineering (bugs, UX, integrations), quantifying demand to inform roadmap.
  
  

Data & Reporting

• Stand up practical dashboards (e.g., Zendesk Explore) for SLAs, deflection, backlog/aging, health signals; drive weekly ops reviews.
  
  

What You'll Bring

• 8–12+ years in B2B SaaS Client Success/Services, incl. 3–5+ years leading CSM/onboarding/support teams.
• Proven ownership of retention/NRR, renewals/expansion, and exec-level stakeholder management.
• Depth in Zendesk operations (Guide/Help Center, macros, triggers/automation, views, SLA policies, Explore).
• Track record of process re-engineering (SOPs, QA, tiering, WFM) delivering measurable efficiency gains.
• Hands-on experience evaluating/implementing AI in support workflows and proving outcomes.
• Nice-to-have: payments exposure (Adyen/Stripe/Paysafe), sports/federation or multi-site SMB experience, bilingual French.
  
  

Benefits & Working Style

• Competitive compensation with performance bonus tied to CS outcomes.
• 10–20% travel for launches, QBRs, and events.
  
  

How to Apply: Submit your resume and a brief note on how you've delivered help-desk efficiency gains (incl. AI) and improved retention/NRR at scale.