Head of Customer Success
On-siteToronto, Ontario, Canada
Job Summary
Design and own the end-to-end customer success strategy, including building journey maps, health scoring models, and scalable playbooks for adoption, renewal, and upsell. Build and manage a high-performing CS team starting with CSMs, defining KPIs, compensation frameworks, and coaching cadences while leading performance reviews. Reduce churn by proactively managing risk and collaborating with Product and Support to resolve issues before escalation. Drive account expansion via contextual upsells and support Marketing with review generation and success story development. Serve as the primary voice of the customer to Product, managing structured feedback loops and leveraging usage patterns to guide roadmap recommendations. Implement tech-touch strategies, optimize HubSpot for lifecycle management, and ensure strong data hygiene across all CS workflows. Partner with Sales, Onboarding, and Client Solutions to ensure smooth handoffs and align on customer readiness metrics.
Required Qualifications
- 5 - 7 years in Customer Success or very similar
- 3+ years in a senior leadership/head-level role in a SaaS company in CS, Onboarding or very similar
- Proven experience scaling a CS function in a B2B SaaS environment with a complex platform
- Deep understanding of customer journeys, lifecycle metrics, and tech-enabled CS strategy
- Proficient with CS and CRM tools, HubSpot (preferred), in-app guidance tools, and feedback collection platforms
- Skilled at building dashboards, defining KPIs, tracking retention/churn/expansion metrics
- Strong interpersonal and communication skills, capable of holding strategic conversations with executives and clients
- Able to roll up sleeves to create from scratch, whether that's processes, teams, leveraging and implementing automation and AI, dashboards, or SOPs
Desired Qualifications
- FinTech/lending/ERP
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