Chief Operating Officer

About Breakthrough Academy

Breakthrough Academy is dedicated to supporting high-achieving entrepreneurs in the contracting sector by enhancing their business growth through effective operational systems. We are committed to unlocking entrepreneurial potential by guiding our Members to overcome challenges and elevate their enterprises via systematic business operations, core skill development, and goal accountability based on a clear business plan.

Established over 11 years ago, Breakthrough Academy has evolved rapidly, presently serving over 750 business owners with the support of an energetic team of 50+ professionals. We lead the contracting industry in implementing systems and processes to improve company operations across North America. Currently, we are entering a new growth phase requiring heightened execution discipline, leadership capabilities, and consistent operations.

Role Overview

We are seeking our inaugural Chief Operating Officer to play a pivotal role in translating strategic direction into operational excellence.

Ideal Candidate Profile

• Proven experience leading senior operational roles in organizations with revenues exceeding $20 million or payrolls over $10 million or teams of 80+ members.
• Accountable for execution across key departments, including Operations, People & Culture, Revenue, and Customer Experience.
• Skilled in establishing structure, accountability, systems, and leadership clarity, especially in founder-led or rapidly scaling businesses.
• Highly execution-oriented with a track record of enhancing ownership, clarity, and follow-through at scale.
• Experience driving revenue performance, not limited to internal operations.
• Expertise improving performance in complex environments with competing priorities.
• Capability to institute structure without causing bureaucratic impediments.
• Demonstrated success in optimizing business execution rather than redefining strategic vision.

Key Responsibilities

• Convert CEO's strategic directions into concrete execution plans spanning Operations, People & Culture, Revenue, Finance, and Member Experience.
• Lead revenue execution by ensuring systems, teams, and processes consistently fuel growth and conversion outcomes.
• Enhance leadership accountability and improve decision-making quality throughout departments.
• Boost operational efficiency through clear structures, defined ownership, and disciplined execution.
• Manage revenue and profitability including forecasting, budgeting input, and margin enhancement in collaboration with the CEO.
• Ensure uniformity and excellence in member experiences across various programs and delivery methods.
• Lead cross-functional strategic initiatives from planning stages through to successful deployment.
• Oversee recruitment, onboarding, and retention efforts organization-wide.
• Manage execution of major company events and internal experiences.
• Proactively identify and resolve operational failures before they impact revenue, delivery, or team performance.

Experience Requirements

• Minimum 5 years in senior operational leadership within companies earning $20 million or more in revenue or handling $10 million in annual payroll.
• Direct ownership over multiple core functions: Operations, People & Culture, Revenue, and Member Experience.
• Proven ability to drive revenue outcomes through operational execution frameworks.
• Accountability for key performance indicators, forecasting, and major operational drivers affecting revenue and profitability.
• A strong record of enhancing execution systems, organizational effectiveness, and leadership responsibility.
• Exceptional project management and communication skills, adept at prioritizing multiple concurrent demands.
• Experience managing multiple department heads with responsibility across operations, personnel, revenue, and delivery.

Benefits

• Function as the CEO’s chief execution partner in a successful, consistently profitable, founder-led business.
• Command the firm's internal operations across core functions including People & Culture, Revenue, Operations, and Member Experience.
• Engage with a fast-expanding technology-driven training company impacting more than 750 business leaders continent-wide.
• Make a substantial difference in Breakthrough Academy's daily operations, scaling and performance.
• Be part of an organization where execution excellence directly influences tangible results for Members.
• Receive a highly attractive executive compensation package involving competitive base salary and performance-based bonuses.
• Gain opportunity for meaningful equity through stock options tying success to personal impact.
• Enjoy exceptional travel perks and company events held in inspiring locations such as Cabo’s beaches and Canmore’s scenic outdoors.