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Chief of Staff

Practice Better

Practice Better

People & HR, Operations
Toronto, ON, Canada
Posted on Thursday, January 18, 2024
Job Title: Chief of Staff
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.
About the Position: We are seeking a dynamic and highly organized individual to join our fast-growing SaaS PLG (Product-Led Growth) company as Chief of Staff. As the right-hand person to the CEO and working very closely with the rest of our Leadership team, you will play a crucial role in driving strategic initiatives, optimizing operational efficiency, and ensuring seamless communication across the organization. This position requires a strategic thinker with excellent communication skills, a proactive mindset, insatiable curiosity, and a passion for driving results in a high-growth environment. This role requires a versatile generalist who can navigate complex organizational challenges and drive multi-disciplinary projects forward.

Responsibilities for the role include:

  • See below for an outline of this role's responsibilities
  • Strategic Planning:
  • Collaborate with the CEO to develop and execute strategic plans that align with the company's vision and goals.
  • Conduct research and analysis to support decision-making processes and potential M&A.
  • Monitor industry trends and competitive landscapes to identify opportunities and risks.
  • Operational Excellence:
  • Streamline and optimize internal processes to enhance overall efficiency and effectiveness.
  • Work closely with department heads to ensure alignment of goals and priorities.
  • Implement and manage KPIs to measure and improve operational performance.
  • Communication and Coordination:
  • Act as a central point of contact between the CEO and various departments, ensuring clear and consistent communication.
  • Facilitate cross-functional collaboration and communication to drive organizational cohesion.
  • Prepare and disseminate internal communications, updates, and reports.
  • Project Management:
  • Oversee and manage key strategic projects from conception to completion.
  • Coordinate project teams, set deadlines, and ensure deliverables are met.
  • Provide regular updates to the CEO and leadership team on project progress.
  • Executive Support:
  • Assist the CEO in managing priorities and time effectively.
  • Prepare data-driven insights, materials, presentations, and reports for executive meetings.
  • Handle sensitive and confidential information with discretion.
  • Crisis Management:
  • Work closely with the leadership team to develop and implement crisis management plans.
  • Act as a key liaison during critical situations, ensuring a swift and coordinated response.


  • Bachelor’s degree in Business, Management, or a related field; MBA preferred.
  • 5-7 years of progressive work experience in a high-growth SaaS company, with a background in management consulting or investment banking.
  • Proven experience in a Chief of Staff, Strategy, or Operations role, preferably within a SaaS PLG environment.
  • Strong analytical and problem-solving skills.
  • Exceptional communication and interpersonal skills.
  • Demonstrated ability to drive initiatives to successful completion.
  • Experience in project management and cross-functional collaboration.
  • Ability to thrive in a fast-paced, high-growth environment.
  • Strategic thinker with a proactive and results-oriented mindset.
  • Bonus: Strong proficiency with SQL or other data querying language

The ideal candidate is:

  • Highly curious — you don’t take current processes/systems/decisions to be set in stone and constantly question if there is a better way. You have a strong desire to constantly learn, understand, and improve, even in highly ambiguous situations. You are inquisitive in nature and proactively seek out new insights/knowledge by not being afraid to ask questions.
  • Has an Owner mentality — You have a very high sense of responsibility and accountability. You are comfortable being a self-starter operating with a high degree of autonomy. You proactively engage in your own work or in cross-functional projects that you are leading.
  • Likes to be a Driver — Your preference is to step up and set the pace on any challenge/task/initiative that requires cross-functional alignment and execution.
  • A master at facilitating a collaborative environment — You are someone who can manage cross-functional, internal and external stakeholders while aligning competing objectives and priorities. You operate with a high degree of emotional-intelligence.
  • Highly data-driven — To the extent that reliable data is available, you actively seek to analyze/investigate using a data-driven approach first, before letting your gut and intuition factor into your decision making.

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.