Senior Enterprise Customer Success Leader

Wellfound; Toronto; Hybrid; CAD 90,000 - 120,000; Full time

Benefits offered by this job

Variable incentive program

Comprehensive benefits

Paid parental leave

Hybrid work model

Mentorship and development

Hybrid in Toronto office – 1 day/week

Job summary

Greenspace in Toronto is seeking a Senior Customer Success Manager to lead a portfolio of large Enterprise customers, ensuring retention, renewal, and growth while translating outcomes into clear value for executives.

You will own multi-site implementations, build executive sponsorships, and partner with Sales to expand usage. A healthcare/digital health background is a plus; strong PM and AI-enabled collaboration are valued. Hybrid work with weekly office presence in Toronto.

Qualifications

• 5+ years in customer success or account management at a SaaS company.
• Track record of retaining and growing complex accounts and renewals.
• Executive presence to run board-room conversations with VP/CEO.
• Experience leading implementations involving change management.
• Strong commercial judgment linking adoption and value to revenue.
• Highly organized with shared project plans across many accounts.
• Empathy to listen, uncover needs, and solve for customers.
• Proactive doer who seeks efficiency and better ways to work.
• Experience with Salesforce, Planhat, Zoom, Slack, Notion, Claude.

Responsibilities

• Own your book of business and be accountable for retention and renewal outcomes.
• Build executive relationships with sponsors, decision-makers, and champions.
• Drive value realization with measurable success metrics and ROI storytelling.
• Grow accounts by identifying expansion opportunities and partnering with Sales.
• Lead complex implementations and change management across multi-site programs.
• Monitor health and risk, develop save plans, and manage escalations.
• Represent the voice of the Enterprise customer to Product, Sales, and leadership.
• Contribute to Enterprise playbooks, processes, and AI-enabled productivity.

Skills

Customer success

Account management

Executive presence

Change management

Project management

Commercial judgment

Empathy

Initiative

Tech-savvy (AI)

Education

Bachelor's degree

Tools

Salesforce

Planhat

Zoom

Slack

Notion

Claude

Job description

Greenspace in Toronto is seeking a Senior Customer Success Manager to lead a portfolio of large Enterprise customers, ensuring retention, renewal, and growth while translating outcomes into clear value for executives.

You will own multi-site implementations, build executive sponsorships, and partner with Sales to expand usage. A healthcare/digital health background is a plus; strong PM and AI-enabled collaboration are valued. Hybrid work with weekly office presence in Toronto.