Head of Customer Success (VP Level)

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Head of Customer Success (VP Level)

role at

Private AI

VP of Customer Success Location: Toronto, Remote Reports to: CEO Team: 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.

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