Fractional Chief of Staff

About the Company

BoomerangFX is a rapidly expanding technology business focused on modernizing how private-pay healthcare practices run their operations. It has been recognized by Deloitte Fast 500 as one of North America’s fastest-growing tech companies for two consecutive years, placing 6th in Canada and 23rd across North America. The company delivers practice management software and digital marketing solutions on a global scale.

Headquartered in Toronto, BoomerangFX also operates from locations in the U.S. (Miami and Las Vegas), the UK, Australia, and Barbados. It is supported by international private equity and is preparing for an IPO. The company has also received Gartner’s Disruptor of the Year recognition and operates with a business model designed to remain resilient in changing market conditions.

Its platform supports healthcare providers in medspas, cosmetic surgery, dermatology, dental, vision, and other private-pay sectors through tools for practice management, EMR, scheduling, lead generation, and digital marketing. These solutions are used by hundreds of clinics to improve revenue, simplify operations, and create better patient experiences.

Role Overview

The Fractional Chief of Staff will act as a senior strategic partner to the CEO, helping ensure company priorities stay aligned and are carried through effectively. This position combines strategy, operations, communication, and leadership, with a strong focus on execution and executive support.

Strategic Planning and Execution

• Drive annual and quarterly planning efforts so goals, KPIs, and priorities are clearly set.
• Turn executive direction into practical roadmaps and initiatives that span multiple teams.
• Track business performance, surface risks early, and suggest corrective steps.

Executive Advisory and Decision Support

• Equip the CEO with analysis, briefing documents, and structured decision-making inputs.
• Build executive presentations, board packs, and strategic memoranda.
• Serve as a trusted advisor on important decisions and confidential matters.

Cross-Functional Leadership

• Align work across Finance, HR, Operations, Product, and other departments.
• Lead or supervise special projects and keep delivery timelines on track.
• Remove blockers between teams and escalate issues when needed.

Internal and External Communications

• Create executive messages, speeches, and company-wide updates.
• Maintain relationships with partners, investors, and senior stakeholders.
• Keep communication consistent across the organization.

Operational Excellence

• Improve internal workflows, meeting structure, and executive operating rhythms.
• Manage recurring leadership meetings, offsites, and quarterly business reviews.
• Put systems in place to monitor priorities, KPIs, and strategic programs.

People and Culture

• Work with HR on leadership development, organizational design, and hiring support.
• Contribute to culture-building and employee engagement initiatives.
• Coach emerging leaders and high-potential team members.

Confidential and Sensitive Matters

• Handle sensitive information with complete discretion.
• Support crisis response, delicate negotiations, and executive-level conflict resolution.

Working Arrangement and Compensation

This is a part-time onsite role based in Mississauga, Ontario, Canada. The schedule is 20 hours per week, spread across 5 half-days. Compensation is USD 70 to 80 per hour.

Qualifications

• A bachelor’s degree and an MBA are required.
• At least 10 years of experience in strategy, consulting, operations, or leadership positions.
• Direct experience working with senior executives.
• A demonstrated history of leading initiatives across functions.

Preferred Experience

• Exposure to startups, SaaS companies, or service-based organizations.
• Prior work in fractional or consulting-style roles.
• Comfort using tools such as HubSpot, Asana, Notion, Salesforce, or BI platforms.