Director of Sales

DIRECTOR OF SALES

• Are you energized by the opportunity to join a founder-led company with real momentum? One that has averaged 72% growth year-over-year for the past 10 years, is entirely self-funded, and is now entering its next stage of scale?
• Do you love taking a strong sales foundation, talented people and proven market demand and turning it into a disciplined, high-performing revenue engine?
• Are you the kind of Sales Leader who spots opportunities others miss? You see how to create more accountability, stronger execution, and predictable revenue performance.
• Have you been looking for a role where you’re not simply managing an established sales team, but stepping into a pivotal leadership role where you’ll shape the next decade of growth? ?
• Do you thrive partnering with ambitious founders who move fast, think big and expect you to translate strategy into measurable results ?
• Are you excited by the opportunity to help professionalize the contracting industry, while improving the businesses and livelihoods of thousands of entrepreneurs across North America?
• Do you want to build something meaningful inside a company that already has the reputation, profitability, market position, and foundation for growth, but still has an enormous runway ahead?

If this sounds like you, read on.

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 entering our next stage of growth, and we're looking for a sales leader who wants more than just hitting quarterly numbers. This is an opportunity to build a high-performing sales team, sales culture, and develop exceptional people.

Because of this, we are looking for our new Director of Sales.

This is where you come in.

THIS IS FOR YOU IF:

• You have 5+ years of experience leading quota-carrying B2B sales teams with direct ownership of team revenue targets and sales performance
• You have consistently achieved or exceeded sales quotas in businesses generating $15M-$30M in revenue, with average deal sizes between $10K-$50K
• Do you thrive building sales cultures where people love to win together? Where coaching is constant, accountability is expected, success is celebrated, and the team genuinely enjoys working alongside one another?
• You are energized by building structure without creating bureaucracy and raising the performance standard while protecting a strong team culture
• You have experience creating and improving outbound sales motions that generated measurable pipeline and reduced reliance on inbound demand alone
• You are a player-coach sales leader who enjoys being close to the business - coaching calls, reviewing opportunities, developing people, and improving execution in real time
• You have a strong balance of sales psychology and sales science to bring both a relational and data driven approach to optimizing the sales process.
• You’re a strategic thinker and problem-solver and understand that sales success is built through measurable performance, including KPIs, forecasting, pipeline management, CRM discipline, and conversion metrics
• You have proven experience improving sales performance through stronger systems, accountability, coaching, and process optimization

IN THE ROLE, YOU WILL BE:

• Leading the Sales organization by creating a disciplined, accountable, and high-performing sales culture capable of delivering predictable revenue growth
• Executing BTA’s sales strategy in alignment with company growth objectives, revenue targets, ideal customer profile (B2B selling to small business owners), and go-to-market priorities
• Building and implementing a strategic outbound sales motion that creates a repeatable pipeline generation engine alongside BTA’s existing inbound sales model
• Establishing clear sales operating rhythms including KPI reviews, forecasting, pipeline management, deal reviews, and performance accountability
• Coaching and developing the Sales Team through consistent 1:1s, call reviews, role plays, deal strategy sessions, and individualized development plans
• Improving sales performance by identifying bottlenecks, optimizing conversion rates, strengthening qualification standards, and improving sales velocity
• Creating stronger alignment between Sales and Marketing by developing feedback loops around lead quality, customer insights, messaging effectiveness, and pipeline opportunities
• Building and maintain sales processes, playbooks, frameworks, and systems that allow the sales organization to scale effectively
• Leading the hiring, onboarding, development, and performance management of future sales team members
• Creating an environment where salespeople are challenged to improve, supported in their development, and held accountable for delivering exceptional results
• Developing future sales leaders and build a sales organization capable of sustaining long-term growth with less dependency on individual contributors

EXPERIENCE REQUIRED

• 5+ years of leadership experience managing quota-carrying B2B digital sales teams
• Direct ownership of annual sales quotas, revenue targets, and measurable team performance outcomes
• Proven track record of consistently achieving or exceeding sales targets in a growth-stage business environment
• Experience leading sales teams in businesses between $15M-$50M in revenue with consultative sales cycles and average deal sizes between $10K-$50K
• Experience building or significantly improving outbound sales programs, prospecting strategies, and pipeline generation initiatives
• Strong understanding of sales operations including CRM management, forecasting, KPI tracking, pipeline reviews, and performance reporting
• Proven experience coaching salespeople, improving individual performance, and developing high-performing sales teams
• Experience operating successfully in founder-led, entrepreneurial, or rapidly growing organizations
• Strong communication, leadership, and problem-solving skills with the ability to balance strategic thinking and hands-on execution

THE BENEFITS

• An opportunity to lead the next chapter of Breakthrough Academy’s sales team and directly influence the company’s continued growth
• Own the evolution of a sales team transitioning from a strong inbound foundation into a balanced, predictable revenue engine
• Work alongside ambitious founders and leadership team members who move quickly, think big, and care deeply about building something exceptional
• Build systems, processes, and a sales culture that will directly impact the future growth of the organization
• Lead a talented team within a company that supports over 750 business owners across North America
• Be part of a company where your leadership directly improves business outcomes for both BTA and the entrepreneurs we serve
• Enjoy a highly competitive compensation package including a strong base salary and uncapped performance-based bonus structure tied to revenue outcomes
• Grow alongside the organization you help build through meaningful career opportunities and leadership growth
• Enjoy amazing travel perks and company events in epic locations - our team experiences 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 sales environment you perform best in, we’d love to hear from you!

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