Managing Director, Sales

Managing Director, Sales


We are looking for an experienced sales leader who is dynamic, driven and enjoys selling as much as coaching and developing a team. This individual can balance the tricky job of working a book of business, along with motivating and supporting a team to success.

On the sales side, this individual has experience and capability in building new relationships and expanding existing ones. They have strong consultative skills and business acumen that helps them connect dots quickly and create compelling recommendations, linked to clients’ business challenges.

On the leadership side, this individual is focused on using a variety of approaches to get the most out of their team. They quickly build trust and confidence in their direct reports, which enables them to work together towards success.


  • Responsible for the development and performance of all sales activities for DDS
  • Staffs and directs a sales team and provides leadership towards the achievement of maximum profitability and growth in line with DDS’s Strategic BluePRINT and values
  • Contributes to the ongoing growth and training & development of sales team members
  • Meets or exceeds personal revenue targets
  • Develops an annual business plan and accompanying sales strategy to ensure attainment of revenue and profitability goals
  • Responsible for the performance and development of the sales team including recruitment, onboarding and ongoing management
  • Manages activity (quantity and quality) and results of the sales team
  • Helps create action plans by individuals as well as by team for effective search of sales leads and prospects
  • Conducts effective one-on-ones (monthly), pipeline reviews (monthly), participates joint calls and facilitates effective sales meetings (weekly) with all sales team members to build more effective communications, to provide insight and achieve sales growth
  • Provides timely feedback to leadership team regarding performance
  • Attend joint calls with salespeople to help them to develop their skills
  • Identify industry trends and provide guidance to sales team members
  • Eventual leadership of DDS marketing

Essential Qualifications & Attributes:

  • 7+ years of sales/sales management experience in a fast-paced environment
  • Passionate about sales and making a difference/impacting others
  • Proven ability to drive results through salespeople at varying levels of experience and tenure
  • Experience using a CRM system for sales and team management (experience with Microsoft Dynamics is an asset)
  • Proven experience as a high performing salesperson (selling intangibles/solutions is an asset)
  • Hunter mentality and capability
  • Strong business acumen
  • High personal work standards and sense of accountability
  • High sense of urgency and success-orientation
  • Ability to work under pressure and manage conflicting priorities
  • Passion for learning, with a strong desire for feedback
  • A dedicated team player with a collaborative mindset

What DoubleDigit Sales Offers:

  • Strong compensation package, including quarterly bonus opportunity
  • Extended Health and Dental Coverage
  • Entrepreneurial culture where personal growth and development is highly encouraged and coached
  • Comprehensive onboarding plan and graduation once you are proficient in the role

About DoubleDigit Sales:

DoubleDigit Sales helps sales leaders and salespeople perform better. As one of the top 20 sales training firms in North America, we offer practical customized sales training programs to drive the right kind of sales behaviours. Our clients realize dramatic and sustainable increases in sales productivity, meeting activity, sales win rates and client experience ratings. For more information please visit

If you are interested in applying for this position, please send your resume to Shannon Holmes at DDS values a diverse and inclusive workplace. Accommodations are available on request for candidates taking part in all aspects of the selection process. We thank you for applying, but only those selected for the interview process will be contacted.