ABOUT BREAKTHROUGH ACADEMYBreakthrough 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 explicit 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 ExperienceYou have implemented structure, accountability, systems, and leadership clarity in founder-led, or notable growth environmentsYou are highly execution driven and have experience driving clarity, ownership, and follow through at scaleYou have proven experience being accountable for revenue execution performance,



not just internal operationsYou have improved performance in businesses with multiple competing priorities and complex delivery environmentsYou’ve been trusted to create structure without creating bureaucracyYou have proven experience improving how a business executes rather than redefining the visionIN THE ROLE, YOU WILL BE:Translating CEO direction into execution plans across Operations, People & Culture, Revenue, Finance, and Member ExperienceDrive revenue execution performance by ensuring systems, teams, and processes consistently support growth and conversion outcomesStrengthen leadership accountability and decision making quality across departmentsImprove operational efficiency through stronger structure, clearer ownership, and more disciplined execution across teamsOversee revenue and profitability performance including forecasting, budgeting inputs, and margin improvement in partnership with the CEOEnsuring consistency and quality of member experience across all programs and delivery channelsLead execution of cross functional strategic initiatives from planning through deliveryLead hiring, onboarding, and team retention across all departments in the organizationOversee execution of key company events and internal experiencesIdentify and resolve operational breakdowns before they impact revenue, delivery, or team performanceEXPERIENCE REQUIRED5+ 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 ExperienceProven experience driving revenue outcomes through operational execution systemsOwnership of key performance metrics, forecasting, and operational drivers of revenue and overall profitabilityProven track record of improving execution systems, organizational performance, and leadership accountabilityExcellent project management and communication skills; comfortable balancing multiple prioritiesExperience directly managing multiple department leaders responsible for operational, people, revenue, and delivery outcomes, with accountability for for execution across all functionsTHE BENEFITSAn opportunity to operate as the CEO’s primary execution partner inside a high performing, consistently profitable, founder-led businessOwn the internal operating engine of the business, across Operations, People & Culture, Revenue, and Member ExperienceWork at the center of a fast growing, tech driven training company, supporting over 750 business leaders across North AmericaCreate a massive impact on how Breakthrough Academy executes, scales, and performs day to dayBe part of a company where execution quality directly shows up in real business outcomes for our MembersEnjoy 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 optionsEnjoy 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 CanmoreIf this role sounds like it aligns with your experience and the kind of operating environment 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.#J-18808-Ljbffr

📌 Chief Operating Officer (Winnipeg)
🏢 Affordable Housing Societies
📍 Winnipeg