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 recent 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: Cambridge

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.

#HP

Accommodations are available upon request for all individuals with disabilities taking part in the recruitment and selection process.

📌 Director of Sales (Cambridge)
🏢 Breakaway Staffing
📍 Cambridge