Software Implementation Specialist:

Windward Software is seeking an Implementation Specialist to join our Client Services team, based out of our sunny Penticton, BC headquarters.

Do you have the ability to effectively communicate with small business owners as well as executives within large organizations? Are you confident with your knowledge of business processes including sales, service, inventory control, accounting, and Customer Relationship Management?

This position requires an individual with a strong understanding of business processes, as well as exceptional customer service and organizational skills.

As an Implementation Specialist, you will be conversing with and supporting Windward clients to:

  • Gain an understanding of their business requirements (online, on-site, and in-house);
  • Communicate information about the Windward implementation process; and
  • Guide and support our clients through each project milestone until the successful launch of their new software is achieved.

You will also be required to present live webinars, create instructional video recordings, and train our clients’ employees on product functionality.


The successful candidate must be able to assemble effective training plans and deliver them to both technical and non-technical audiences in a variety of settings, including via telephone, online, in-classroom and on-site.

You must be process-oriented and have a technical aptitude as you will be responsible for managing multiple projects at any given time and be required to resolve customer issues by troubleshooting to identify issues and provide resolution.


A business related post-secondary degree with related work experience is preferred, however equivalent business experience in the areas of accounting, business management, teaching experience and/or project management experience would be seriously considered.

** Bilingual English/French is an asset.

Due to the international nature of Windward Software and the locations of our clients, a valid driver’s license and Passport are required for this role. Monthly travel could be expected, and a flexible schedule is required to fulfill the responsibilities of this role.


  • A comprehensive benefits package;
  • Lakes, beaches, wineries - all in our backyard! Take your lunch break at beautiful Skaha Beach - literally just a block away;
  • A huge staff lounge area with gym equipment, pool table and showers on-site;
  • Tickets for events at the South Okanagan Events Centre (SOEC); and
  • Social activities such as golf tournaments, holiday festivities, etc.

Interested? Send your details to us at and don’t forget a cover letter!  While we appreciate all interest, only those selected for further review will be contacted.  Thank you.

Job Info

Location: Penticton, BC, Canada

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