Client Service Specialist:

Windward Software is seeking a knowledgeable and talented problem-solver to join our Client Service Team, based out of our 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?

As a Client Service Specialist, you will be facilitating the implementation of our software as well as assisting clients to resolve technical difficulties via the telephone.

This position requires an individual with a unique blend of:

  • Business process knowledge;
  • Exceptional customer service and organizational skills,
  • Effective verbal communication skills;
  • Outstanding problem-solving skills within a technical environment; and
  • Advanced knowledge of PC hardware, operating systems, software installations and configuration, some database knowledge and basic networking and printer knowledge.

From an Implementation stand-point, you will be responsible for:

  • Gaining an understanding of each client's business requirements (online, on-site, and in-house);
  • Communicating information about the Windward implementation process; and
  • Guiding and supporting our clients through each project milestone until the successful launch of their new software is achieved.

In regard to the technical support aspects of the role, you will be responsible for:

  • Fielding technical support calls in a professional manner and working to resolve each to the respective client's satisfaction, in a timely fashion.

You will also be required to present live webinars, create instructional video recordings, and train 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 will also become an expert of our flagship business management product, Windward System Five, and apply this knowledge in solving reported technical issues via the telephone.

The successful candidate 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 relevant work experience is preferred, including previous work providing technical support services; however, equivalent business experience in the areas of accounting, business management, teaching experience and/or project management experience will be seriously considered.

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 position.

We offer a fun, yet professional working environment. We celebrate successes and birthdays, and hold golf tournaments and other social activities. It doesn’t hurt that our office is a stone's throw from the beach! Discounted gym memberships, a games room and other benefits are also offered to our employees.

To confirm: this is not a remote work position; it is based on-site in our Penticton, BC headquarters.

Interested? Send your resume to us at and include a cover letter telling us why you'd be a great fit for our team.  While we appreciate all interest, only those selected for further review will be contacted.

Job Info

Location: Penticton, BC, Canada

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