We are seeking a bold, modern Director of Sales to lead a sales organization through a transformational shift to the Challenger Sales Model.
This role is for a true sales leader – someone who lives and breathes Challenger every day, challenges customer thinking, coaches relentlessly, and builds a culture of accountability, insight, and performance.
This individual will be responsible for driving growth across new and existing customers while building, inspiring, and developing a high-performing sales team aligned to a single, disciplined sales methodology.
Compensation & Benefits:
– Base Salary: $140,000-$150,000/year
– Variable Compensation: Incentive structure developed collaboratively with the CEO
– Benefits and RRSP details to be confirmed
Location: Tri-Cities area (Kitchener/Cambridge/Waterloo)
What You’ll Lead:
– Own and embed the Challenger Sales Model across the entire sales organization
– Build a culture of ‘teach, tailor, take control’ through daily coaching and leadership
– Lead business development, proposal management, and a team of 5-6 sales hunters
– Assume responsibility for the Marketing function, including oversight of the marketing program and staff member, ensuring tight sales – marketing alignment
– Drive new customer acquisition while strengthening and expanding existing client relationships
– Position solutions that clearly demonstrate ROI, reduce risk, and solve complex customer challenges
Team Performance & Incentives:
– Drive accountability, execution, and measurable results across the sales team
– Coach and develop high-potential sales talent
– Design and implement an incentive program that motivates performance and aligns with company goals
The Ideal Leader:
– Proven sales leader with experience closing complex, consultative deals
– Deep familiarity with (and passion for) the Challenger Sales Model
– Strong people leader who coaches, challenges, and elevates performance
– Strategic thinker with hands-on execution ability
– Industry experience preferred, but exceptional leadership and sales methodology expertise take priority
If this sounds like you, please apply now.
This position is for a new position with our client. By applying to this position you agree to allow Breakaway Staffing to contact you via email, text, or phone call communication regarding this job application.
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