Chief Revenue Officer

Chief Revenue Officer – Breakthrough Academy

Are you energized by the idea of stepping into a founder-led company with real momentum? One that has averaged 72% growth year-over-year for the past 10 years, has generated over $100M in revenue fully self-funded, and did it all without a revenue executive in place?

Do you thrive on transforming proven businesses into their next stage of growth by building world class revenue engines, making smarter growth investments, and creating the systems required to scale?

Have you built scalable revenue systems that consistently produce predictable growth, rather than relying on individual performers or founder instinct?

Do you enjoy leading high-performing Sales and Marketing teams, setting the strategic direction while empowering an exceptional team to execute?

Do you naturally think in funnels, customer acquisition, positioning, RevOps, brand, conversion, and long-term growth strategy instead of simply chasing next month’s numbers?

Are you excited by the opportunity to help professionalize and elevate an entire industry, while directly improving the businesses, livelihoods, and quality of life of entrepreneurs across the entire continent?

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 through a clear business plan.

Breakthrough Academy is now 11 years old and evolving rapidly, with 750+ business owners developing inside our program, and an incredible team of 55 individuals who make an impact on our members every single day. We’re now entering one of the most exciting chapters in our company’s history. We have a proven market, a strong brand, an incredible community of Members, and a tremendous opportunity ahead of us. We’re looking for the right leader to help us build on that foundation and unlock the next level of revenue growth.

Because of this, we are looking for our first ever Chief Revenue Officer, an executive who will play a defining role in shaping the future of Breakthrough Academy.

This Is For You If:

• You’ve built and scaled sophisticated B2B digital marketing engines in a $10M-50M business that consistently generated qualified demand, improved marketing ROI, and fuelled sustainable revenue growth.
• You have deep expertise in B2B digital marketing and know how to turn marketing investment into predictable, profitable revenue growth.
• You have a track record of improving ROI by making smart commercial decisions about where to invest, what to optimize, and what to stop doing.
• You have experience evaluating and scaling multiple growth channels, including digital acquisition, partnerships, events, and other strategic growth opportunities.
• You have built high-performing digital marketing teams by creating a culture of ownership, clarity, urgency, collaboration, and measurable results.
• You know how to build marketing strategies that create predictable pipelines, not just campaigns that generate activity.
• You have successfully unified Sales and Marketing under one commercial strategy, creating alignment, accountability, and shared ownership of revenue growth.
• You thrive in founder-led businesses where there is significant opportunity to shape strategy, build enterprise value, and directly influence the company’s next stage of growth.

In The Role, You Will:

• Own and optimize Breakthrough Academy’s marketing system – improving customer acquisition strategy, channel performance, and return on marketing investment.
• Develop and execute a scalable B2B demand generation strategy across digital channels, partnerships, events, customer referrals and emerging growth opportunities.
• Bring strategic discipline to our growth investments by identifying the highest-leverage opportunities across marketing, channels, partnerships, and market expansion.
• Transform our approach to demand generation by evaluating our current growth engine and building a more predictable, scalable path to revenue.
• Shape our go-to-market strategy by refining our Ideal Customer Profile, positioning, messaging, and approach to reaching business owners across North America.
• Create a data driven system that improves visibility into acquisition performance, conversion, forecasting, and revenue outcomes.
• Unify Marketing and Sales around a shared revenue strategy, creating alignment between market demand, pipeline generation, and customer growth.
• Identify new opportunities for growth through strategic partnerships, events, pricing, packaging, and additional revenue opportunities.
• Lead and develop the Vice President of Marketing and Director of Sales, creating clarity, accountability, and a high-performance culture across the revenue organization.
• Partner directly with the CEO to shape Breakthrough Academy’s next phase of revenue growth, making the strategic decisions that will define the future of the company.

Experience Required

• 10+ years of deep expertise building and scaling B2B digital marketing teams, with a proven ability to turn marketing investment into measurable revenue growth.
• Previous experience as a Vice President Marketing, Vice President Growth, Vice President Revenue, Chief Revenue Officer or equivalent commercial leadership role within a $15M-$50M+ B2B organization.
• A proven track record of scaling B2B customer acquisition through digital marketing, demand generation, and multi-channel growth strategies.
• Experience owning significant marketing budgets and making strategic investment decisions tied directly to revenue outcomes, ROI, and business growth.
• Experience building and optimizing go-to-market strategies, including positioning, ICP development, channel strategy, and market expansion.
• Experience leading both Sales and Marketing functions, with accountability for revenue performance and commercial alignment.
• Experience hiring, developing, and leading leaders within a high growth organization.
• Prior experience scaling a founder-led or entrepreneurial business where strategy, structure, and operating discipline needed to evolve alongside growth.

The Benefits

• Own one of the most important growth opportunities in Breakthrough Academy’s history, shaping the commercial strategy that will define our next stage of revenue scale.
• Partner directly with the CEO and leadership team, having a meaningful voice in company strategy, growth priorities, and the decisions that shape the future of the business.
• Join a company that has built remarkable momentum, averaging 72% year-over-year growth for the past decade, serving 750+ business owners across North America, and entering its next phase of growth.
• Have the opportunity to build a world-class revenue organization, combining strong existing foundations with your own strategic vision and leadership.
• Create measurable impact every day by helping entrepreneurs across North America build stronger businesses, improve their livelihoods, and create more opportunities for their teams and families.
• Be part of a company where execution quality directly shows up in real business outcomes for our Members.
• Work alongside an ambitious leadership team that values ownership, excellence, continuous improvement, and doing meaningful work together.
• Enjoy a highly competitive executive compensation package that includes a strong base salary, performance based bonus structure, and long term equity participation through stock options.
• Enjoy amazing travel perks and company events in epic locations – our team events this year ranged from the warm beaches of Baja Mexico to the serene mountains of Canmore, Alberta.

If you’re an experienced revenue leader looking for an opportunity to architect the next stage of growth inside a profitable, founder-led business with tremendous momentum, we’d love to hear from you.