Head of Customer Success (VP Level)

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

You'll thrive here if you're both a builder and a coach. Someone who can create structure where none exists, obsess over customer outcomes, and develop a team that scales with the business. Our team runs on high trust and high transparency—you'll have freedom to experiment, move fast, and make the calls without waiting for permission.

• 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.