Customer Success Manager

Job title: Manager, Customer Success

Location: The candidate must be located in Canada or the USA. Our HQ office is located in Toronto, ON, Canada, but the role is remote/hybrid/flexible. 

Reporting to: VP of Customer Experience

How we work:

Practice Better operates remote-first, hybrid optional. We ensure each team member is equipped with the necessary tools to perform effectively within the comfort of their own space. However, flexibility is important! So, if you need to stretch your legs or whiteboard with your team, you can use our beautiful, private downtown Toronto office.

About the Role:

To achieve our ambitious goals, we’re looking for a strategic leader and hands-on Manager, of Customer Success. This is a unique and high-impact opportunity to shape how Practice Better engages and supports its entire customer base through digital and scaled programs. In this role, you’ll play a critical role in designing and delivering innovative, outcome-driven customer experiences that make an immediate and lasting impact across all of our customers. We have a strong foundation of customers wanting to grow their use of Practice Better. Our opportunity is to continue to enhance how we help them by engaging more effectively and proactively through our digital and scaled channels.

You’ll partner closely with Product and Marketing teams to define and execute a comprehensive customer orchestration strategy tailored to key moments in the post-sale journey. Your team will empower customers to adopt, expand, and realize ongoing value from the Practice Better platform through an omnichannel, one-to-many approach.

Success in this role requires an innovative program builder who is deeply passionate about the customer experience, excels at cross-functional collaboration, and thrives in driving measurable outcomes. You’ll play a critical role in crafting tech-touch experiences and digital motions that are not only scalable but genuinely valued by customers—ensuring they feel informed, supported, and engaged at every stage.

You will lead a lean but high-leverage Customer Success team (starting with four direct reports) and oversee the following key areas:

• Onboarding
• Scaled & Digital Customer Success

This is a unique opportunity to help build the next chapter of Practice Better’s growth by investing deeply in our customer experience.

What You’ll Do

In this role, you will:

• Develop and implement end-to-end digital and one-to-many programs for customers, as well as leading the teams tasked to execute this strategy 
• Create and execute a cohesive strategy with tangible goals, consistent performance, and tracking of key metrics to drive adoption, retention and expansion for our customers
• Provide thought leadership as we evolve our Customer Success vision
• Collaborate with Practice Better leaders across Support, Product and Marketing to align on customer needs, prioritize opportunities, and accelerate usage, retention and growth
• Champion a test-and-learn culture that continuously improves self-service, digital education, and pooled outreach programs
• Build and maintain meaningful connections with key customer stakeholders to understand their evolving priorities, helping the team uncover opportunities where Practice Better can drive platform value and business outcomes
• Coach and develop the team by providing regular feedback, setting clear expectations, and investing in each team member’s growth
• Foster a healthy, inclusive team culture where team members feel supported, connected, and empowered to do their best work

Who You Are

• 5+ years of customer success experience in a high growth SaaS environment
• 3+ years leading a team in a similar capacity, ideally within a PLG SaaS business
• Proven success building digital and one-to-many success motions from scratch with a sharp focus on execution, measurement, and iteration
• Strong understanding of SaaS metrics (GRR, NRR, activation, adoption, etc.) and how to influence them
• You give and receive feedback well, set clear expectations, and keep stakeholders informed and aligned
• You focus your team on business impact—not just activity—and use data to guide decisions and measure success
• Excellent collaboration, communication, and cross-functional influence
• You lead with empathy, prioritize team wellbeing, and create an inclusive environment where everyone can do their best work
• Highly organized, decisive, and comfortable with managing complex priorities in a fast-paced environment
• Hands-on and pragmatic; no task is beneath you if it helps the team move forward

Nice to Have: 

• Health and Wellness, passion or industry experience considered an asset

What We Offer

Comprehensive Benefits
We offer a robust benefits package for full-time, permanent employees, including health, dental, and vision coverage from day 1, as well as RRSP matching, generous paid parental leave, and annual learning stipends.

Remote-First, Connected CultureOur remote-first model gives you autonomy and flexibility, with optional access to our downtown Toronto office for in-person collaboration. We also host regular off-sites and team gatherings across North America, because connection, creativity, and shared moments matter.

Wellness and Growth

• Unlimited vacation, built on trust, clear expectations, and real support for taking time off
• Company RRSP program with employer-matched contributions
• Comprehensive health and dental benefits from day 1
• $750 annual Health & Wellness Allowance
• $1,000 annual Learning & Development Allowance to support your growth
• $500 annual Home Office Allowance to set up a productive remote workspace
• Sprout Family: personalized support for family-building and fertility journeys
• Inkblot: confidential, digital mental health support from licensed professionals
• Company-wide holiday closure in December
• Regular virtual company-wide events, lunches, and team socials to stay connected