ABOUT BREAKTHROUGH ACADEMY

Breakthrough Academy specializes in helping high performing entrepreneurs in the contracting industry grow their businesses by implementing excellent operational systems into their companies. We believe in the unlimited potential of entrepreneurship and help our Members (customers) break through barriers and take their businesses to the next level. Our proprietary training program brings systemization to a contracting company’s operations, develops an entrepreneur’s core business skills, and holds accountability to goals along a clear business plan.

Breakthrough Academy is now 11 years old and evolving rapidly, with over 750 business owners developing in the program, and an awesome team of 50+ running the show. We are leaders in the contracting industry, helping companies across the continent to implement systems & processes into their operations. We’re now entering our very own next stage of scale where execution discipline, leadership capability, and operational consistency are critical to growth.

Because of this, we are looking for our first ever Chief Operating Officer.

This is where you come in.

THIS IS FOR YOU IF:

You have led senior operational responsibilities in a $20M+ revenue business (or equivalents: $10M in annual payroll or 80 person team size)

You have owned execution across multiple core functions including Operations, People & Culture, Revenue, and Customer Experience

You have implemented structure, accountability, systems, and leadership clarity in founder-led, or notable growth environments

You are highly execution driven and have experience driving clarity, ownership, and follow through at scale

You have proven experience being accountable for revenue execution performance, not just internal operations

You have improved performance in businesses with multiple competing priorities and complex delivery environments





You’ve been trusted to create structure without creating bureaucracy

You have proven experience improving how a business executes rather than redefining the vision IN THE ROLE, YOU WILL BE:

Translating CEO direction into execution plans across Operations, People & Culture, Revenue, Finance, and Member Experience

Drive revenue execution performance by ensuring systems, teams, and processes consistently support growth and conversion outcomes

Strengthen leadership accountability and decision making quality across departments

Improve operational efficiency through stronger structure, clearer ownership, and more disciplined execution across teams

Oversee revenue and profitability performance including forecasting, budgeting inputs, and margin improvement in partnership with the CEO

Ensuring consistency and quality of member experience across all programs and delivery channels

Lead execution of cross functional strategic initiatives from planning through delivery

Lead hiring, onboarding, and team retention across all departments in the organization

Oversee execution of key company events and internal experiences

Identify and resolve operational breakdowns before they impact revenue, delivery, or team performance

EXPERIENCE REQUIRED

5+ years in a Senior operational leadership role within a $20M+ revenue business (or $10M in annual payroll)

Direct ownership of multiple core functions including Operations, People, Revenue, and Member Experience





Proven experience driving revenue outcomes through operational execution systems

Ownership of key performance metrics, forecasting, and operational drivers of revenue and overall profitability

Proven track record of improving execution systems, organizational performance, and leadership accountability

Excellent project management and communication skills; comfortable balancing multiple priorities

Experience directly managing multiple department leaders responsible for operational, people, revenue, and delivery outcomes, with accountability for for execution across all functions THE BENEFITS An opportunity to operate as the CEO’s primary execution partner inside a high performing, consistently profitable, founder-led business

Own the internal operating engine of the business, across Operations, People & Culture, Revenue, and Member Experience

Work at the center of a fast growing, tech driven training company, supporting over 750 business leaders across North America

Create a massive impact on how Breakthrough Academy executes, scales, and performs day to day

Be part of a company where execution quality directly shows up in real business outcomes for our Members

Enjoy a highly competitive executive compensation package that includes a strong base salary, performance based bonus structure.

Succeed alongside the organizational growth you help create through meaningful stock options

Enjoy amazing travel perks and company events in epic locations – our team events this year range from the warm beaches of Cabo to the serene outdoors in Canmore

If this role sounds like it aligns with your experience and the kind of operating setting you perform best in, we’d love to hear from you!

We thank you for your time and interest. We will reach out directly to shortlisted applicants.

📌 Chief Operating Officer (Winnipeg)
🏢 Bilinguallink
📍 Winnipeg