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Senior Sales Executive - SkillsWave (Canada Based)



Sales & Business Development
Kitchener, ON, Canada · Remote
Posted on Wednesday, May 8, 2024

D2L is a cloud company that is modernizing education and building the Future of Work. The old models of teaching and learning are in the midst of the largest transformation in history, and D2L is at the heart of that fundamental shift.

New models of teaching and learning enable a personalized, student-centric experience – and deliver improved retention, engagement, satisfaction, and results for learners of all ages – in schools, campuses, and companies.

D2L is disrupting the way the world learns, by providing the next generation learning environment and solutions to engage and inspire learners. And most importantly, by giving customers a platform that is easy, flexible, and smart. No other company provides a solution as robust and innovative as D2L.

D2L has had a singular mission for 20 years and is dedicated to that same mission in the years ahead: to transform the way the world learns – and by doing so, we will help improve human potential globally.

A member of our Talent Acquisition team reviews ALL of our applications - yes a real person reviews resumes! They are excited to read more about what amazing things you could add to D2L.

PLEASE NOTE: D2L announced a planned spin-out of the D2L Wave product into a standalone independent company. This role will be a part of the new entity known as SkillsWave, and post-close will not be affiliated with D2L.

SkillsWave is a dynamic upskilling and education-as-a-benefit company dedicated to empowering individuals and organizations to thrive in the rapidly evolving landscape of work. Our innovative approach combines cutting-edge technology with personalized learning experiences to equip employees with the skills they need to succeed in their careers. To do this, we need to give talented, enthusiastic, and passionate people opportunities to create, develop, and collaborate on projects that revolutionize the learning environment.


As a Senior Sales Executive you will be responsible for meeting and exceeding sales objectives of the assigned territory by promoting and selling the SkillsWave product through professional sales techniques. We are looking for a highly knowledgeable and capable senior sales individual with a proven track record of selling high-value solutions within education-as-a-benefit and corporate training space. The Senior Sales Executive must possess an in-depth knowledge of Corporate training. The individual will spend the majority of their time in the field developing and cultivating prospects, moving them through the sales process and closing new business.


  • Meeting and exceeding set sales quotas for defined area/region within education-as-a-benefit and corporate training
  • Make prospecting an integral part of your regular routine ensuring new prospects are being added to the sales funnel on an ongoing basis
  • Managing a complex, enterprise solution sale with a 6 month to 12 month purchasing cycle.
  • Moving the sale through the entire sales process actively engaging other SkillsWave resources as necessary to ensure success
  • Taking an instrumental role in the RFP process
  • Continually learning about new products and improving your selling skills. The Senior Sales Executive will be required to attend training events throughout the year and will be expected to participate in self-paced tutorial learning when appropriate
  • Being well informed about current industry trends and being able to talk intelligently about the education industry in the assigned area/region
  • Becoming familiar with all SkillsWave Partner relationships and how they relate to SkillsWave sales
  • Effectively using the sales CRM tool to enter all sales information into this system
  • Attending and participating in sales meetings, product seminars and trade shows
  • Preparing written presentations, reports and price quotations
  • Assisting in contract negotiations
  • Building and managing a quantifiable 12 month sales pipeline
  • Effectively and efficiently deploying SkillsWave resources at appropriate stages in the sales cycle to advance the sales process
  • Developing positive relationships with other employees in Marketing, Professional Services, Finance, Engineering and other departments as needed


  • 5+ years’ sales experience in the eLearning, education, and/or complex solution software sales industries. Knowledge of education-as-a-benefit and corporate training space preferred.
  • Successful achievement of 1M+ quotas, consultative enterprise/solution or technical sales
  • Ability to manage a pipeline of 50+ accounts at any given time
  • Ability to work in a team environment
  • Proven success prospecting, building a pipeline, moving opportunities through the sales cycle; proposing, presenting and discussing solutions with C-level and other decision-makers
  • Ability to craft a solution with appropriate products and services that meets business goals based on client discussions
  • Working knowledge of web and database technology
  • This position requires the Senior Sales Executive to work out of their home as base of operations
  • Must possess strong leadership, motivational, and presentation skills
  • Must be able to travel up to 25% of the time


  • Bachelor's degree recommended (technical, business or education-related is ideal)

Don’t meet every single requirement? We strongly encourage you to still apply! At D2L, we are committed to creating a diverse and inclusive environment. We encourage your application even if you don't believe you meet every single qualification outlined, because we love to help our people grow and develop!

Why we're awesome:

At D2L, we are dedicated to providing you with the tools to do the best work of your life. While some of our perks and benefits may vary depending on location or employment type, we are proud to provide employees with the following through #LifeAtD2L;

  • Impactful work transforming the way the world learns
  • Flexible work arrangements
  • Learning and Growth opportunities
  • Tuition reimbursement of up to $4,000 CAD for continuing education through our Catch the Wave Program
  • 2 Paid Days off for Catch the Wave related activities like exams or final assignments
  • Employee wellbeing (Access to mental health services, EFAP program, financial planning and more)
  • Retirement planning
  • 2 Paid Volunteer Days
  • Competitive Benefits Package
  • Home Internet Reimbursements
  • Employee Referral Program
  • Wellness Reimbursement
  • Employee Recognition
  • Social Events
  • Dog Friendly Offices at our HQ in Kitchener, Winnipeg, Vancouver and Melbourne.