Manager – Customer Success

Position Summary

We are looking for a Manager, Customer Success to join our growing team.

To achieve our ambitious goals, we’re looking for a strategic and hands-on Customer Success leader. 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.

Note: Practice Better is a remote-first company with team members across North America. However, this particular role is currently open to Canadian-based candidates only, and preference will be given to applicants legally authorized to work in Canada.

What You’ll Be Doing

• Design and execute end-to-end digital customer journeys — onboarding sequences, lifecycle campaigns, in-app guidance, webinars, and automated outreach — that drive activation, adoption, and retention across the full customer base
• Own scaled (1:M) engagement strategy: build the playbooks, define the triggers, and instrument the motions that move customers from sign-up to sustained value through one-to-many and tech-touch channels
• Lead and develop a lean CS team spanning Onboarding and Customer Success, setting clear goals and coaching for impact
• Partner cross-functionally with Product, Marketing, and Support to align on customer needs, close feedback loops, and accelerate platform usage
• Define and track key CS metrics (GRR, NRR, conversion rate, time-to-value, adoption milestones) — use data to prioritize programs, prove ROI, and iterate fast
• Champion a test-and-learn culture: run experiments on self-service, digital education, and pooled outreach programs; kill what doesn't work, double down on what does
• Build and maintain customer health visibility across the base, identifying risk signals and expansion opportunities at scale
• Contribute to the broader CS vision as PB evolves its post-sale engagement model
• 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

What You Bring

• 5+ years in Customer Success with 2+ years leading a team — ideally in a PLG or product-led SaaS environment
• You've built scaled or digital CS programs from scratch: lifecycle email campaigns, automated journeys, one-to-many webinars, pooled outreach, or similar
• Strong command of SaaS metrics (GRR, NRR, activation, adoption, churn) and how CS programs move them
• Data-driven and operationally sharp — comfortable with health scores, product usage data, dashboards, and using signal to guide decisions
• Experienced with CS or engagement tooling (e.g., HubSpot, Intercom, ChurnZero, Gainsight, or similar) and able to architect workflows across them
• Excellent cross-functional operator — you influence without authority and keep Product, Marketing, and Support aligned on customer outcomes
• Hands-on leader who coaches with empathy, sets clear expectations, and builds inclusive team culture
• Pragmatic program builder: you'd rather ship something imperfect and iterate than wait for perfect

Compensation & Pay Transparency

At Practice Better, we believe in pay transparency, equity, and fairness. We benchmark compensation against similar-stage, high-growth SaaS companies in both Canada and the United States and review our salary bands regularly to ensure they remain competitive and aligned with market trends.

Each role has a defined pay range based on its level, scope, and geographic location. Final offers are determined by several factors, including experience, demonstrated skills, and location, to ensure consistency and equity across our team.

Anticipated Salary Range (Canada): $95,000 – $120,000/yr CAD

We take a holistic approach to compensation, combining salary, bonus, equity, benefits, and flexibility. Our goal is to provide total rewards that support both your professional growth and personal well-being.

The range above reflects our expected compensation for this role, based on current market data. Final offers may vary depending on factors such as location, skills, depth of experience, and relevant certifications. All compensation ranges are reviewed regularly and may evolve over time to reflect changes in the market.

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