Fractional Chief of Staff

BoomerangFX; Mississauga; On-site; CAD 60,000 - 70,000; Part time

Job summary

BoomerangFX is seeking a highly organized Fractional Chief of Staff to partner with the CEO, drive top priorities, and enable efficient decision-making in a fast-growing environment. This on-site role at our Mississauga, ON office is 20 hours per week with a competitive CAD 60 per hour.

You will work with leadership to ensure organizational alignment, manage cross-functional initiatives, and support scaling for international growth while balancing strategic planning with hands-on execution.

Qualifications

• 5-8+ years in strategy, operations, consulting, or Chief of Staff roles.
• Experience in high-growth SaaS/tech/healthcare preferred.
• Strong business acumen for moving between strategy and execution.
• Exceptional communication and stakeholder management.

Responsibilities

• Drive CEO priorities from strategy to execution with accountability.
• Serve as proxy for the CEO in meetings ensuring alignment and follow-through.
• Align teams around OKRs and growth objectives; remove roadblocks.
• Lead cross-functional initiatives and scale programs across orgs.
• Prepare executive communications, board decks, and investor updates.
• Develop HR strategies, workforce planning, and scalable processes.
• Oversee talent acquisition and onboarding; strengthen recruitment practices.

Skills

Strategic thinking

Executive communication

Stakeholder management

Operations experience

C-level collaboration

Fast-paced environment

Prioritization

Ambiguity handling

Job description

This is your chance to build a meaningful career in a high-growth, entrepreneurial environment as we lead the charge towards IPO. If you're ready to challenge the status quo and make an impact, we invite top talent to join us on this exciting journey.

Job Type: Part-Time

****The role is PART-TIME (20 HOURS A WEEK, 5 HALF DAYS) based on site in Mississauga, ON, with a rate of $60/hour***

You will work closely with the leadership team and may be expected to be available during core business hours for meetings or urgent matters.

Why Join BoomerangFX?

BoomerangFX isn't just a company— it's a movement redefining how private pay healthcare practices operate. Recognized as one of North America's Fastest Growing Tech Companies two years in a row by Deloitte's Fast 500 program ranking 6th in Canada and 23rd in North America. We are a global leader in practice management software and digital marketing solutions. Our growth trajectory of over 8000% is matched by our ambition to disrupt and dominate the healthcare technology landscape.

With offices across the USA, Canada, UK, Sydney, and India, we’re building a truly global organization and expanding our presence in international markets. This is an exciting opportunity to join a high-growth company and play a meaningful role in shaping and supporting our continued international growth.

Your Role in a Nutshell

As a Fractional Chief of Staff, you will act as a strategic partner to the CEO, driving execution on top priorities, ensuring organizational alignment, and enabling efficient decision-making across the business. This role is ideal for a highly organized operator who thrives in fast-paced, high-growth environments and can balance strategy with hands-on execution.

Key Responsibilities

Strategic Execution & CEO Enablement

• Drive the CEO's top priorities from strategy through execution, ensuring accountability and results.
• Act as a thought partner to the CEO, helping refine strategic initiatives and business priorities.
• Serve as a proxy for the CEO in meetings, ensuring alignment and follow-through.

Cross-Functional Alignment

• Align teams around company OKRs, strategic initiatives, and growth objectives.
• Identify and remove execution roadblocks across departments.
• Facilitate communication and collaboration between leadership and functional teams.

Operational Excellence & Special Projects

• Lead high-impact, cross-functional projects from concept to completion.
• Build systems, frameworks, and processes to improve organizational efficiency and clarity.
• Support scaling initiatives across operations, go-to-market, and internal infrastructure.

Executive Communication & Reporting

• Prepare executive communications, board decks, and investor updates.
• Track and report on key metrics, initiatives, and company performance.
• Ensure consistent messaging across internal and external stakeholders.

Strategic HR Leadership

• Partner with leadership to develop and execute HR strategies aligned with business goals.
• Advise on organizational design, workforce planning, and culture development.
• Identify and implement scalable HR processes as the company grows.

Talent Acquisition & Onboarding

• Oversee or support recruitment processes, including job postings, interviews, and offer letters.
• Help standardize hiring practices and ensure a positive candidate experience.
• Design and manage onboarding programs for new hires.

Employee Relations & Engagement

• Serve as a trusted advisor for employee concerns, conflicts, and performance issues.
• Create and execute initiatives that foster employee engagement, satisfaction, and retention.
• Conduct stay and exit interviews to gather feedback and improve processes.
• Develop and maintain employee handbook, HR policies, and procedures.
• Ensure legal compliance with federal, state, and local employment laws and regulations.
• Keep up with HR best practices and advise leadership on implications of policy changes.

Performance Management

• Help define and implement performance review processes and feedback systems.
• Provide coaching and support for managers and employees around goal-setting, growth, and accountability.
• Advise on compensation strategy, salary benchmarking, and equity structures (if applicable).
• Assist in evaluating, selecting, or managing benefits providers and offerings.

HR Systems & Reporting

• Recommend or manage HRIS systems suitable for a small or growing team.
• Maintain accurate employee records and generate HR reports as needed.

Qualifications

• 5-8+ years of experience in strategy, operations, consulting, or Chief of Staff roles.
• Background in high-growth environments (SaaS, tech, healthcare preferred).
• Strong business acumen with the ability to move between strategic thinking and execution.
• Exceptional communication, organizational, and stakeholder management skills.
• Proven ability to manage multiple priorities in a fast-paced, ambiguous environment.
• Experience supporting C-level executives is highly preferred.

Why This Role Is Unique

• Work directly with the CEO and executive team on high-impact initiatives.
• Influence company-wide strategy and execution in a high-growth environment.
• Flexible, fractional structure with meaningful ownership and visibility.
• Opportunity to help scale a company on a path to IPO.

BoomerangFX is an equal opportunity employer committed to diversity and inclusion. We welcome applications from all qualified individuals and will provide accommodations throughout the hiring process upon request.