Senior Customer Success Manager

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

At Greenspace, our mission is to empower mental health organizations, health systems, service providers and individuals in care with the technology and expertise they need to substantially improve how services are accessed, measured and delivered.

The Role

We are looking for a commercially minded, highly organized, and customer-obsessed Customer Success leader to join our Enterprise Success team as a Senior Customer Success Manager. You will own a portfolio of our largest and most strategic customers, acting as a trusted advisor to their clinical, operational, and executive leaders. You will be accountable for the long-term health, retention, and growth of your accounts, and for making sure every customer can clearly see the value Greenspace delivers. Your work will directly contribute to our mission of improving mental health outcomes while fostering a culture of collaboration and excellence.

What You'll Do

• Own your book of business. Be accountable for retention, renewal, and expansion outcomes across a portfolio of Enterprise customers, including accurate renewal forecasting and early identification of risk.
• Build executive relationships. Identify and engage executive sponsors, decision-makers, and operational champions. Lead Leadership Account Reviews and Executive Business Reviews that connect platform usage to the outcomes our customers care about.
• Drive value realization. Partner with customers to define success metrics, track progress, and build a clear ROI story that supports renewal and growth.
• Grow accounts. Identify expansion opportunities across users, programs, and modules, and partner with Sales to progress them.
• Lead complex implementations and change management. Guide multi-site and multi-stakeholder rollouts, including workflow design, training, and adoption planning, while managing a clear shared project plan.
• Get ahead of risk. Monitor customer health and satisfaction, act early on warning signs, and own save plans and escalations through to resolution.
• Be the voice of the Enterprise customer. Translate customer evidence into clear, prioritized input for Product, Sales, and leadership.
• Raise the bar for the team. Contribute to Enterprise playbooks, processes, and tools, including how we use AI to work smarter, and share what you learn with other CSMs.

What You Bring

• 5+ years in customer success or account management at a SaaS company, with direct ownership of Enterprise accounts and renewal outcomes.
• A track record of retaining and growing complex accounts, including navigating at‑risk renewals and sourcing expansion.
• Confident executive presence. You can run a board‑room conversation with a VP or CEO, handle a tough question with composure, and tailor your message to clinical, technical, and business audiences.
• Experience leading implementations of complex products involving change management, workflow transformation, and multiple stakeholders.
• Strong commercial judgment. You understand how adoption, value, and relationships translate into revenue.
• Highly organized, with experience managing shared project plans, timelines, and documentation across many accounts in a fast‑paced environment.
• Genuine empathy. You listen first, uncover the unspoken need, and then solve.
• You're a doer and you take initiative. You don't wait to be told what to focus on, and you're always looking for ways to make your work more efficient.
• Comfortable with tools like Salesforce, Planhat, Zoom, Slack, Notion, and Claude, and curious about using AI to improve how you work. The ability to learn new technologies quickly matters more than any specific tool.
• Bachelor's degree from an accredited post‑secondary institution.
• Bonus: Experience in healthcare, behavioral health, digital health, or selling into health systems and public‑sector organizations.

About Greenspace

Founded at St. Michael's Hospital in Toronto, Greenspace was created to bridge the gap between the proven benefits of Measurement-Based Care in research and its implementation in practice. Our solutions are designed to empower organizations to use data to inform treatment decisions and significantly improve the quality of mental health care across North America.

Our Culture

As a fast‑paced health technology company, there is an opportunity for all staff to play a pivotal role in the growth of our company. We are driven by a passion for improving mental health care and the lives of millions of people. We foster a collaborative environment where all ideas are valued, whether they come from our CEO or our newest team member.

Diversity

Diversity strengthens our organization, and we are committed to being an equal‑opportunity employer. We recruit, employ, train, and promote employees regardless of race, religion, color, national origin, gender, age, sexual orientation, gender identity, or disability.

Compensation & Benefits

• Participation in variable incentive program tied to your territory's retention and expansion revenue.
• Comprehensive benefits program, including paid parental leave.
• Healthy work/life balance - we recognize that building a startup is a marathon, not a sprint.
• Tight-knit collaborative work environment where we work in teams rather than siloed individuals.
• Ongoing mentorship, coaching, and personal development opportunities.
• Remote/in‑person hybrid work setting based in Toronto, Ontario, with one day per week in our downtown office.