Head of People

Role: Head of People

Location: The candidate must be located in Canada, with a strong preference for someone local to the greater Toronto area. Our HQ office is located in Toronto, ON, Canada, but the role is remote/hybrid/flexible.

How we work:

Practice Better operates remote-first, hybrid optional. We ensure each member of our team 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:

At Practice Better, our people are our greatest lever for impact. As we grow rapidly in the dynamic and competitive health & wellness landscape, the strength, cohesion, and effectiveness of our team become more important than ever. We’re looking for a Head of People who will play a mission-critical role in building the infrastructure, culture, and practices that unlock our team’s full potential so that we can continue delivering exceptional outcomes for our customers, partners, and each other.

This is not just a leadership position – it’s a foundational role that will shape the future of how we attract, retain, develop, and empower top talent. You will partner closely with the leadership team, the Head of People will be a strategic advisor, operational leader, and cultural steward. You will set the bar high, driving clarity and excellence while fostering a sense of purpose, equity, and belonging across the organization.

We’re looking for someone who brings a thoughtful, measured approach to building a world-class People function – balancing the urgency of a high-growth environment with the need for scalable, enduring systems. You’re energized by a fast-paced environment, but you don’t confuse speed with haste – you take the time to find the right answers, guided by strong principles and a commitment to high standards. You’re someone who doesn’t just react quickly, but responds wisely – with empathy, accountability, and a commitment to long-term impact.

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

• People Operations & Compliance
• Talent Acquisition & Employer Branding
• Performance Management & Leadership Development
• DEIB Strategy & Employee Experience
• People Analytics & Strategic Workforce Planning

This is a unique opportunity to help build the next chapter of Practice Better’s growth by investing deeply in what matters most: our people.

What You’ll Do:

Strategic Leadership & People Planning

• Partner with the executive leadership team to design, drive, and own a People strategy that helps create the conditions for growth & excellence
• Serve as a strategic advisor on org design, team capacity planning, and performance management
• Facilitate clear, productive, and candid discussions with leadership, proactively surfacing insights, identifying risks, and driving the team toward stronger alignment and better outcomes

People Operations, Compliance & Systems

• Oversee the delivery and continued optimization for a seamless People operations (including leveraging AI) in onboarding, offboarding, leave management, benefits
• Ensure legal compliance and policy implementation across all relevant jurisdictions in the U.S. and Canada
• Optimize our HRIS and tech stack (e.g., BambooHR, Lattice) to streamline reporting, analytics, and team experience
• Build repeatable, scalable processes and measure outcomes against clearly defined success criteria

Talent Management

• Own and evolve our talent management philosophy and programs, ensuring individuals and teams have clear expectations, meaningful development opportunities, and a supportive environment where accountability and growth go hand-in-hand
• Develop and implement tools and frameworks for goal-setting, feedback, performance reviews, and career development

Talent Acquisition & Employer Brand

• Lead our recruiting function in partnership with our lead recruiter, focusing on hiring velocity, candidate quality & experience, and process optimization & consistency
• Develop and refine strategies to attract exceptional talent across functions
• Lay the foundation for our employer branding strategy, defining how we tell our story externally, crafting our unique value proposition as an employer, and collaborating across teams to elevate the candidate experience

Culture, DEIB & Engagement

• Design and deliver meaningful culture programs that reinforce inclusion, psychological safety, and employee belonging
• Run regular employee listening mechanisms (e.g., our quarterly eNPS surveys) and translate insights into action, in partnership with our People Operations Coordinator
• Develop & lead DEIB efforts with intentionality, ensuring alignment with our values and the communities we serve

Who You Are:

• Self-directed, highly motivated People leader with 7+ years in People Ops or HR leadership roles in either Canada and/or the U.S. (ideally within tech or high-growth environments)
• An experienced people manager with 3+ years leading and coaching other managers
• Adept at building and scaling People programs from scratch, with a sharp focus on execution, measurement, and iteration
• A clear communicator and trusted advisor who can influence up, down, and across the organization
• Extremely empathetic and service-oriented; the ideal candidate will work in service of creating exceptional experiences and interactions to serve our internal customers: our people
• Highly organized, decisive, and comfortable with managing complex priorities in a fast-paced environment; a role modeling culture carrier that is open to, flexible with, and adaptable to change, and capable of setting a high bar and driving accountability
• Skilled at delivering direct, constructive feedback and facilitating courageous conversations
• Hands-on and pragmatic; no task is beneath you if it helps the team move forward
• Proficient in People tech systems (e.g., BambooHR, Lattice), Google Suite, and project tracking tools (e.g., Notion)

Our Perks and Benefits:

• Unlimited Vacation: We believe you can be highly productive and still have plenty of time for life outside of work.
• Generous health benefits plan: Coverage starts from Day 1 and includes vision & dental.
• RRSP / 401K matching program for retirement savings.
• Sprout Family: Receive personalized support for the family-building process, accessing top-quality care. Schedule a consultation with Sprout's Team for guidance, education, coaching, and assistance in finding a top provider, addressing medical, legal, or regulatory concerns throughout your journey. *Currently for Canadian Employees Only*
• Inkblot: Access to one of Canada's leading digital mental health companies, focusing on offering secure online video counseling through our corporate mental health programs and individual counseling services. *Currently for Canadian Employees Only*
• Choose your device: Are you Team Windows or Apple? You shouldn’t have to compromise, especially if you work more efficiently on a specific operating system. When you join us, you get to pick!
• Home Office Allowance: $500/year to ensure your home office is set up for optimal comfort and productivity.
• Health & Wellness Allowance: $750/year to support your health & wellness-related goals and hobbies.
• Learning & Development Allowance: $1000/year to explore a new skill, attend a conference, read some new books, etc.
• Fully Remote: Work from the comfort of your own home with the choice to access our downtown Toronto office for a change of scenery.
• Events & Free Lunches: We prioritize weekly team bonding and monthly company-wide social events with a lunch stipend. We pride ourselves on maintaining a culture where everyone feels engaged, inspired, and excited to come to work every day.