About Us

We are a virtual-first primary care organization reimagining how people access and experience healthcare. Our mission is to deliver comprehensive, high-quality, and compassionate care that integrates technology, data, and human connection through a seamless digital platform complemented by in-person visits when needed. While our care is provided exclusively to patients in the United States, our team is distributed across the United States and Canada, bringing together clinicians, technologists, and operators who share a commitment to making high-quality healthcare delightful, personal, and accessible to everyone.

Description

As the Director of People & Culture, you will serve as the senior HR leader for our distributed team across the United States and Canada. You will be responsible for building, developing, and retaining high-performing teams who embody our mission and values.

This is a strategic and hands-on role that spans the full people function: from total rewards and performance management to talent development, succession planning, and HR operations, while ensuring compliance with employment legislation in both countries. You will report directly to the CEO and serve as a trusted advisor to leadership, using data and HR key metrics to inform strategic decisions and drive organizational effectiveness.

This position is open to remote candidates located across Canada and the United States, with preference given to candidates based in the Montreal area.

Responsibilities:

Total Rewards

• Design, manage, and continuously evolve competitive compensation and benefits programs for both US and Canadian employees, ensuring market alignment, internal equity, and regulatory compliance.

• Conduct and analyze compensation benchmarking studies to inform salary structures, pay bands, and incentive programs across both countries.

• Oversee equity compensation programs, including administration and reporting within Carta, ensuring accuracy for all employee equity grants, vesting schedules, and cap table management.

• Manage all benefits programs (medical, dental, vision, disability, life insurance, RRSP/401(k) matching) across both jurisdictions, partnering with brokers and vendors to optimize offerings.

• Partner with Finance to develop and maintain the total compensation budget, ensuring cost-effectiveness while remaining competitive in the market.

Performance Management

• Build and lead a consistent, fair, and effective performance management framework that supports employee growth, accountability, and organizational results.

• Design and operationalize performance review cycles, goal-setting processes (OKR/MBO), continuous feedback mechanisms, and calibration sessions across all levels.

• Leverage ADP and other HRIS tools to manage performance workflows, automate review cycles, and generate actionable reporting for leaders.

• Partner with managers and senior leadership to address performance issues, coach employees through improvement plans, and support equitable, data-informed promotion decisions.

Talent Management & Career Development

• Develop and implement a comprehensive talent management strategy encompassing talent acquisition, onboarding, retention, and internal mobility across the US and Canada.

• Build structured career pathing frameworks and development programs that support merit-based advancement and long-term employee engagement.

• Design and deploy learning and development initiatives, including leadership development programs, skills training, and access to professional growth resources.

• Conduct regular talent assessments and stay/exit interview analysis to identify trends, risks, and opportunities within the workforce.

• Manage and optimize the full employee lifecycle using ADP, ensuring seamless onboarding, records management, compliance tracking, and offboarding.

Succession Planning

• Lead succession planning processes for key and critical roles across the organization, ensuring business continuity and leadership pipeline health.

• Partner with the CEO and senior leadership to identify high-potential employees, assess readiness, and create individualized development plans for future leaders.

• Maintain and regularly update a succession readiness map, incorporating talent reviews and performance data to guide organizational decisions.

• Proactively identify capability gaps and recommend hiring, development, or restructuring strategies to address them.

HR Operations & Compliance (US & Canada)

• Oversee all HR operations across Canada and the United States, maintaining full compliance with applicable federal, provincial/state, and local employment legislation, including Quebec labor law.

• Administer and optimize ADP as the primary HRIS platform, ensuring accurate employee data, payroll coordination, compliance reporting, and system efficiency.

• Create, maintain, and enforce HR policies, employee handbooks, and standard operating procedures for both geographies.

• Manage the full employee lifecycle — from talent acquisition and onboarding through performance management and offboarding — with equitable, consistent, and legally compliant practices.

• Partner with legal counsel and Finance on cross-border employment matters, contractor classification, and regulatory changes affecting the workforce.

HR Metrics & Executive Reporting

• Define, track, and present key HR metrics and KPIs to the Leadership team on a regular cadence, including headcount, attrition, engagement scores, time-to-fill, offer acceptance rates, compensation ratios, and performance distribution.

• Build and maintain HR dashboards and reports that translate data into strategic insights, enabling evidence-based decisions on workforce planning, retention, and culture investment.

• Use data from ADP, Carta, and other platforms to identify trends, flag risks, and surface recommendations to senior leadership proactively.

Strategic HR Leadership

• Act as a trusted advisor to the CEO and senior leadership team on all people matters, including organizational design, headcount planning, culture, and change management.

• Lead and develop the People & Culture team through periods of growth and transformation, modeling strong leadership and fostering a high-performance culture.

• Partner with Finance to develop, manage, and optimize the People & Culture budget, ensuring responsible resource allocation.

• Stay current on HR trends, emerging best practices, and regulatory changes across North America through continuous professional development and industry engagement.

Skills / Qualifications Required

• 10+ years of progressive HR experience, including at least 5 years in a leadership role (e.g. HRBP, Senior Manager, Head of or Director of People) across Canada and the US.

• Proven ability to develop and execute HR strategies aligned to business goals, including organizational change management, workforce planning, talent development, and employee engagement.

• Hands-on experience with HR operations (recruitment, onboarding, performance management, compliance, and HRIS implementation).

• Strong track record managing compensation, benefits, budgets, and HR metrics/KPIs to inform decision-making.

• Strong understanding of relevant HR legislation, federal and local employment laws, and workplace best practices in both Canada and the US (Quebec experience preferred).

• Expertise in employee relations, coaching, and culture-building, with commitment to diversity, equity, and inclusion.

• Experience leading and mentoring HR teams through growth and organizational change.

• Fluently bilingual (English/French), proficient in verbal and written communications in both languages. This is essential for communicating effectively with our local team and stakeholders across Canada and the US.

• Willing to travel to Montreal on a quarterly basis if not living in Montreal.

Skills / Qualifications Preferred

• Proven track record with other startups or VC funded companies.

• Experience with a large non-exempt hourly workforce.

• Human Resources Professional Certification (e.g., CRHA).

• Experience with ADP, Slack, Notion, Carta, MS Office and Google Suite.

Compensation

Our compensation is market-aligned, performance-led, and designed to ensure internal equity. We review pay regularly, with progression tied to demonstrated impact and expanded scope rather than tenure alone. Final offers are tailored to each candidate’s skills, experience, qualifications, and location within the applicable regional pay band.

• Canadian base salary range: $140,560 to $175,700 CAD.
• U.S. base salary range (varies by location): $144,080 – $213,100 USD. Compensation is adjusted based on location, with higher ranges for high-cost areas such as San Francisco, mid-range for markets like Chicago, and lower ranges for other U.S. locations.

Benefits

Please note that specific benefits vary by country and location of employment. Your recruiter will confirm the exact package available to you during the interview process.

• Paid Time Off: Flexible vacation, sick leave, and 12 statutory holidays.

• Health & Insurance: Medical, Dental, Vision, Disability, and Life insurance.

• Wellness: Mental health programs and an Employee Assistance Program (EAP).

• Retirement: RRSP/401(k) program with company match up to 4%.

• Development: Annual reimbursement for eligible training and professional programs.

• In-Office Perks: Monthly lunches and team events for Montreal in-office employees.

Circle Medical is an equal opportunity employer and affirmatively seeks diversity in its workforce. Circle Medical recruits qualified applicants and advances in the employment of its employees without regard to race, color, religion, gender, sex, sexual orientation, gender identity, gender expression, age, disability, genetic information, ethnic or national origin, marital status, veteran status, or any other status protected by law.