Head of People

People /
Full-time, Remote /
Job Title: Head of People
Location: Candidate must be located in Canada or the USA. Our office is located in Toronto, ON, Canada, but the role is remote/hybrid/flexible.
Reports to: CEO

About us:
Practice Better is a leading all-in-one practice management software solution transforming how health & wellness professionals run their practices and support their clients. The company serves 15,000+ customers in over 70+ countries across the globe, and processes hundreds of millions annually in payments on behalf of customers. Over 65% of growth in our customer base comes from word of mouth and referrals, which is a testament to our strong brand and community. Practice Better has recorded a 300% compound annual growth rate in revenue since inception, and we are well-positioned for continuous growth in the years to come

Position Overview:
As the Head of People, you will be pivotal in shaping and executing the people strategy to support our overall business objectives as we enter our next growth phase. We have doubled our team size in 2023 and expect to do the same in 2024, with an experienced People Leader guiding us. The ideal candidate cares deeply about building the best employee experience, balancing culture-building and value alignment with operational and compliance best practices in an early-stage, growth-focused environment. If this sounds like you, we’d love to hear from you!

This key leadership position will drive initiatives related to the following core pillars:

    • Talent Acquisition and Retention
    • Employee Engagement and Manager Development
    • Diversity, Equity, and Inclusion
    • Organizational Effectiveness and People Operations
    • Compliance with employment laws and regulations

Key Responsibilities:

    • See below for an overview of the key Responsibilities of this role

    • Strategic People planning and setting the vision of the People Team:
    • Ability to align People strategies with overall business goals and contribute to the company's long-term success.
    • Visionary thinking to anticipate and address future talent needs. Conduct workforce planning and anticipate future skills and talent needs.

    • Talent Acquisition and Retention:
    • Strong expertise in talent acquisition strategies to attract, hire, and retain top talent.
    • Implementation of effective onboarding processes and retention programs.

    • Employee Engagement and Development:
    • Focus on employee satisfaction and engagement to foster a positive and inclusive culture. The eNPS is your best friend.
    • Ownership of initiatives that enhance employee development and professional growth, including key activities like performance reviews and compensation philosophy.
    • Play an active role in culture building for the entire team by building annual social calendars, curating inclusive events, and other team-building activities.

    • Leadership with strong communication skills:
    • Strong leadership qualities to guide and inspire the People team and influence organizational culture, with the ability to lead change initiatives and drive People-related projects forward.
    • Excellent communication skills to articulate People strategies, policies, and initiatives with openness and transparency to promote trust with both the People team and the broader company.

    • Emotional Intelligence:
    • High emotional intelligence to understand and navigate the complexities of human relationships and workplace dynamics, having the empathy and the ability to connect with employees at all levels.
    • Strong conflict resolution skills to address employee relations issues and mediate conflicts within the workplace

    • Data-Driven Decision-Making:
    • Utilization of analytics and data to make informed decisions about talent management, workforce planning, and employee engagement.
    • Implementation of KPIs to measure effectiveness of the People function.

    • Technology Proficiency:
    • Familiarity with technology and tools to streamline processes, improve efficiency, and enhance the employee experience. This includes owning our global HRIS, ATS, internal wiki, performance evaluation, and payroll related software and tools.

    • Legal and Compliance Knowledge:
    • In-depth understanding of employment laws, regulations, and compliance requirements to ensure the organization operates within legal boundaries.
    • Proactive management of People-related risks and legal issues.

    • Global Perspective:
    • Experience in managing the People function in a global context, considering cultural differences and local employment practices.
    • Knowledge of international labor laws and regulations, specifically in Canada and the US.


    • 6-8+ years of progressive leadership experience leading a People function at scale, preferably in a high-growth startup environment.
    • You have experience managing the People function of a scaling SaaS company, supporting teams across North America. Global experience is a plus.
    • You are a leader with a proven ability to build and lead high-performing teams with a growth mindset, a natural curiosity, and a strong commitment to learning and development.
    • You are comfortable with a high level of accountability and autonomy. You are comfortable with change and adapt well to new challenges while stepping outside your comfort zone.
    • You leverage data to inform & drive decision-making but are also comfortable using your instincts as needed.
    • You have deep expertise in building the technology stack needed for a high-growth company with a global workforce. Managing people ops and employee experience is a plus.
    • You have a strong attraction to the company's mission, vision, and values and can confidently champion them across the company.
    • Strong knowledge of employment laws and regulations.
    • Bonus: You have experience scaling an organization from 50 to 200+ employees.

Perks & 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.
    • 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.
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.

We appreciate all applications, but only those selected for an interview will be contacted.

Practice Better is a respectful, caring, and inclusive workplace. We are committed to accessibility, diversity, and equal opportunity. Requests for accommodation can be made at any stage of the recruitment process providing the applicant has met the requirements for the position. Applicants need to make their requirements known when contacted.
Practice Better is proud to be a diverse and equal opportunity employer and as such does not discriminate on the basis of race, color, religion, sex, national origins, age, sexual orientation, disability, or any other characteristic protected by applicable laws. Selection decisions are solely based on job-related factors.