Director of Customer Success:

Location: Hybrid (Remote-first, must be based near Toronto)

Compensation: $110,000-$130,000 CAD base + health benefits + unlimited vacation (min. 3 weeks)

Hours: Monday-Friday, 9am-5pm EST (occasional off-hours work may be required)

Reports to: CEO

About the Company

Our client is a mission-driven PropTech SaaS company providing digital solutions that enhance communication, engagement, and operational efficiency. They support a growing portfolio of clients across real estate, service, and community-focused sectors, and are entering an exciting stage of growth following strong momentum in both product development and customer acquisition.

To support this next phase, they are seeking a Director of Customer Success to lead their post-sales operations, overseeing both onboarding and account management. This role requires a balance of strategic leadership and hands-on execution, with the opportunity to shape how customer success scales alongside the business.

The Role

As Director of Customer Success, you will take full ownership of the customer lifecycle-from onboarding to support to ongoing account management-with the goal of maximizing satisfaction, retention, and long-term growth. You'll lead and mentor a cross-functional team while identifying and executing strategies that enhance the customer experience at every stage.

Reporting directly to the CEO, you will influence product direction, shape internal processes, and ensure operational excellence across all customer-facing functions. The ideal candidate combines hands-on initiative with strong people leadership, a collaborative mindset, and a proven ability to drive outcomes. You'll work closely with Product and Engineering to represent the voice of the customer internally, and you'll bring valuable insights to company leadership and investors as the business continues to scale.

Responsibilities

• Own the entire customer success operation, from onboarding, support, account management, and retention
• Manage and coach a team of 6 direct reports, including onboarding specialists, customer support representatives and (as needed) account managers.
• Map out and refine CS workflows; identify inefficiencies and close process gaps
• Maintain and improve reporting and customer data accuracy in HubSpot
• Report customer KPIs (churn, LTV, satisfaction) to the CEO and executive team
• Lead high-touch customer engagement and resolve escalations with care and urgency
• Partner cross-functionally to ensure a strong feedback loop between CS, Product, and Engineering
• Enable expansion through customer advocacy and upsell/cross-sell opportunity identification

Requirements

• 5+ years of experience in customer success or account management roles
• 3+ years of team leadership experience (SaaS or tech startup background strongly preferred)
• Proven ability to improve customer retention, satisfaction, and operational clarity
• Strong understanding of onboarding, customer lifecycle management, and support workflows
• Hands-on experience with CRM systems - HubSpot preferred
• Strong reporting and analytics mindset; able to share actionable insights with leadership
• Effective communicator with a customer-first mindset and a knack for building trust quickly
• Comfortable working in fast-paced, evolving environments with limited structure

Nice to Have

• Industry experience in real estate tech, property management, or payments
• Familiarity with Jira, Slack, and remote-first collaboration tools
• Experience with customer success analytics and board-level reporting
• Exposure to upsell/cross-sell strategies in post-sales customer engagement