Director Sales Enablement and Operations

Restaurant Partnerships Winnipeg, MB


We have something other delivery apps don’t have: exclusive partnerships with some of the largest and most popular restaurants in Canada. More and more brands each day, both independent and national chains, choose to deliver with Skip. With your passion for building and managing long-lasting relationships, you’ll help us continue to expand our reach while setting our partners up for success. You’ll also create continuous, irresistible value that keeps everyone satisfied.

The Director of Sales Enablement and Operations will be responsible for managing the processes, administration, technology and training for enabling the sales and account management team at Skip to perform at maximum effectiveness. 

Reporting to the SVP of Restaurants, the Director will be an essential leader in driving revenue growth, efficiency and transformational sales and account management initiatives. The leader will collaborate directly with the heads of growth and account management in designing the environment for success. This leader will be counted upon to provide experience, expertise and thought leadership to execute sales territory management, compensation plans, KPI creation and reporting, learning and development, systems, tools and processes to govern daily operations. 

In addition, this person will bring an analytical capability that enables Skip to continually improve performance and drive new revenue growth. The leader will be a key member of the Restaurant organization leadership team.

What Is On Your Plate: 

  • Lead the function focused on enabling and supporting both the sales and account management organizations
  • Provide strategic leadership to design and administer all sales processes, policies and programs to drive sales and account management effectiveness and productivity
  • Build territory management, lead generation processes, and sales reporting capabilities to optimize sales performance
  • Establish KPI’s and build integrated dashboards and reports across the entire Restaurant organization
  • Oversee the administration and execution of sales team targets, compensation plans, and KPIs to increase effectiveness and drive growth
  • Relentlessly analyze the business and proactively offer insights and recommendations to the sales and executive leadership team
  • Get your hands dirty. Analytical rigour and strategic thinking are essential, but we’ll also need you to get your hands dirty to help drive real sustainable impact. Should be just as willing to have a strategic conversation about sales process as building Salesforce/CRM reports to track the efficiency of the sales and account management teams.
  • Be the liaison between Sales, Marketing and Operations to identify opportunities to improve operational efficiency and productivity, and strengthen communication and camaraderie between organizations
  • Design and implement sales and account management compensation plans that align with company objectives, motivate sales staff, and drive productive behavior
  • Collaborate with sales leaders and our Learning & Development team to design sales and account management training programs to optimize individual and team performance
  • Design / evaluate / implement technology and programs to improve productivity across the restaurant organization
  • Oversee the administration of all enterprise software applications used by the sales and account management team. Salesforce experience is a plus.
  • Identify opportunities for sales process improvements and create a new level of consistency for all team members
  • Develop, coach and inspire a sales operations and enablement organization that facilitates the growth and development of sales and account management competencies and performance

Recipe For Success: 

  • Leadership experience managing Sales Operations function in fast-growing, high-transaction volume, inside and outside sales and account management organizations in technology industry including consulting, sales operations, B2B and B2C environments
  • Experience in global B2B sales enablement process management, business analytics, technology and compensation management strategy
  • Exceptional people leader: acquire, develop and retain top industry talent to perform beyond expectations
  • Strong strategic, analytical ability and intellectual curiosity to drive performance improvement and solve business challenges
  • Change management leadership ability to administrate process improvements in large scale sales operations
  • Technology junkie, with direct Salesforce CRM experience a MUST.
  • Cross-functional collaboration and influence ability at senior most levels of an organization
  • Team playing collaborator with highest levels of integrity
  • Highly organized, but entrepreneurial with a desire to act quickly
  • Strong leader—action oriented and leads from the front

What It’s Like To Work At Skip 

Picture this: you, dressed in your fave casual attire, amongst a team of friendly and passionate colleagues. You feel pride knowing your input and uniqueness is not only embraced, but makes an impact on a major Canadian company, and its satisfied customers. As the company grows, so do you — you meet and surpass new challenges every day. 

Those mentioned above are just a taste of what it’s like to work at one of Canada’s leading tech companies. If you’re hungry for opportunity, growth, and something meaningful in a dynamic, yet casual environment, we’d love to hear from you. 

Note: All employees will be asked to sign a Consent for Disclosure of Personal Information in order to complete a background check. Job offers will be conditional upon results that the Company determines to be satisfactory.