The Head of Customer Success will lead the customer success strategy, focusing on retention, expansion, and overall customer outcomes, ensuring a proactive approach to customer management and developing the CS team and processes.
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.
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