Director of Executive Operations

About the Company

BoomerangFX is a fast-scaling healthcare technology business focused on how private-pay practices run and grow. The company has been recognized by Deloitte’s Fast 500 program as one of North America’s fastest-growing tech companies for two consecutive years, ranking 6th in Canada and 23rd in North America. It operates as a global provider of practice management software and digital marketing tools, with an expansion pace of more than 8000% and a long-term goal of reshaping the healthcare tech market.

Headquartered in Toronto, the company also maintains offices in Miami, Las Vegas, the UK, Australia, and Barbados. It is supported by international private equity and is preparing for an IPO. The business has also been named Gartner’s Disruptor of the Year and is built around a resilient model in a growing market.

Its platform supports healthcare providers in medspas, cosmetic surgery, dermatology, dental, vision, and other private-pay segments through integrated tools for practice management, EMR, scheduling, lead generation, and digital marketing. These solutions are used to help clinics increase revenue, improve operations, and deliver better patient experiences.

About the Role

The Director of Executive Operations acts as a senior strategic partner to the CEO, helping align the organization, move cross-functional initiatives forward, and ensure executive priorities are carried through effectively. This position combines strategic thinking, operational discipline, communication, and leadership, while also serving as a trusted advisor and force multiplier.

Strategic Planning and Execution

• Drive annual and quarterly planning cycles by defining goals, KPIs, and priority areas with clarity.
• Turn executive vision into practical roadmaps and cross-department initiatives.
• Track business performance, flag risks early, and suggest corrective steps when needed.

Executive Advisory and Decision Support

• Support the CEO with analytical insights, briefing documents, and decision-making frameworks.
• Create executive presentations, board-ready materials, and strategic memoranda.
• Serve as a trusted thought partner on sensitive and high-stakes matters.

Cross-Functional Leadership

• Align work across functions such as Finance, HR, Operations, Product, and related teams.
• Lead or oversee special initiatives and ensure deliverables and deadlines stay on track.
• Identify blockers between teams and raise issues proactively to the right stakeholders.

Internal and External Communications

• Prepare executive messages, speeches, and company-wide updates.
• Maintain relationships with investors, partners, and senior stakeholders.
• Keep messaging consistent across internal and external audiences.

Operational Excellence

• Improve internal workflows, meeting structures, and executive operating rhythms.
• Run the cadence of the business, including leadership meetings, offsites, and quarterly reviews.
• Create systems to monitor priorities, KPIs, and strategic projects.

People and Culture

• Work with HR on leadership development, organizational structure, and hiring efforts.
• Contribute to culture-building and employee engagement initiatives.
• Coach emerging leaders and high-potential employees.

Confidential and Sensitive Matters

• Manage confidential information with discretion and care.
• Support crisis response, delicate negotiations, and resolution of executive-level conflict.

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 alongside senior executives is necessary.
• A demonstrated history of driving cross-functional programs and initiatives.

Preferred Background

• Experience in startups, SaaS companies, or service-based organizations is preferred.
• Exposure to fractional or consulting-style engagements is an advantage.
• Familiarity with tools such as HubSpot, Asana, Notion, Salesforce, or BI platforms is helpful.

Compensation and Additional Details

• Base compensation is CAD 100,000 to CAD 120,000 per year.
• There is also a 15% performance-based bonus.
• Employees become eligible for the company stock option plan after six months of continuous employment.
• The role requires working in the office five days per week in Mississauga, Ontario.