Head of Customer Success

Join to apply for the Head of Customer Success (VP Level) role at Private AI VP of Customer Success Location: Toronto, RemoteReports to: CEOTeam: 2 Direct Reports We're a venture-backed Series A company in a hot space, growing fast, with money in the bank. We're looking for a hands‑on customer success leader to own retention, expansion, and customer outcomes end‑to‑end—partnering closely with the CEO and sales to turn customers into advocates and account growth. What we offer Competitive salary + meaningful equity Health/dental/vision, flexible PTO, remote-friendly A direct line to the CEO and real influence on company strategy The chance to build the customer success function from first principles—proactive, measurable, and customer‑obsessed What you'll own Retention & Expansion: Build a proactive account management function with clear ownership of post‑sale relationships. Set expansion quotas alongside retention metrics and develop account planning frameworks focused on growth opportunities. Customer Health & Risk Management: Deploy automated health scoring based on usage patterns, feature adoption, support sentiment, and engagement. Create intervention playbooks and lead weekly account reviews to catch churn risk early. Onboarding & Time‑to‑Value: Own the customer journey from signature to first value. Implement readiness assessments, 30/60/90‑day success milestones, and celebrate early wins to maintain momentum. Sales‑to‑CS Handoff: Design and enforce a seamless handoff process—standardized templates, warm handoff meetings, shared context repositories, and a 30‑day overlap period with Sales. QBRs & Executive Engagement: Transform QBRs from status updates into value‑delivery sessions with insights, benchmarks, and actionable recommendations. Maintain executive sponsorship through ROI dashboards and roadmap previews. Tiered Support Model: Build differentiated SLAs by customer tier, establish clear escalation paths, and implement tools to increase support capacity. Team & Process: Develop the CS team, (Director of CS + Solutions Engineer); Own the CS tech stack and build the playbooks that scale. What success looks like (12 months) A dedicated account management function with clear ownership and proactive customer engagement Net revenue retention above 100% through systematic expansion and reduced churn Faster time‑to‑value with structured onboarding and clear success milestones A customer health system that identifies risk early and triggers the right interventions QBRs that drive expansion, not just check boxes A small, high‑output team you've mentored and developed Day‑to‑day Set and hit quarterly retention and expansion targets with the CEO and sales leader Run weekly account reviews; prioritize at‑risk customers and expansion opportunities Partner with Sales on handoffs and with Product on customer feedback loops Coach your team on strategic account management and difficult customer conversations Share crisp retention insights and next actions each week You’ll thrive here if you 7–12+ years in B2B SaaS with direct ownership of retention and expansion at Series A–B Deep customer success and account management experience (health scoring, QBRs, renewal playbooks, expansion motions) Strong operational instincts (segmentation, tiering, automation, dashboards) Proven ability to build and lead teams from early stage Builder’s mindset: clear priorities, proactive engagement, bias to action Nice to have Experience with technical products or technical account management models Background in both Customer Success and Solutions Engineering Familiarity with our buyer personas and industry Track record of implementing CS platforms and automation How to apply Send a short note, resume/LinkedIn, and 2–3 examples of customer success wins (with context, approach, and results). Include one retention or expansion target you owned and how you hit it. #J-18808-Ljbffr