Our People, Our Product

This is a tough business. We are selling software to business owners to help them run their entire companies effectively and efficiently. The purchase of a business management system is critical, and it represents a huge decision for the business owner. And this is where we come in.

Careers at Windward Software

Windward System Five is a fully integrated business management software solution designed to help businesses around the world since 1984. We understand business and we’re confident our business management system will improve a business's bottom line.

With offices in four countries, we have a diverse team of exceptional people. If you would like to join our team, current opportunities are posted on this page. As we maintain a database of resumes for future openings, and you’re invited to submit your resume and cover letter after viewing the typical position requirements below.

For all positions at Windward Software, we look for excellent customer service and communication skills, a great work ethic and a natural drive to succeed. These are attributes that cannot be taught. While we prefer experience and/or knowledge in the areas of common business practices, accounting principles, inventory control, and point of sale, our in-house training program is designed to provide the training for the right individual.

We foster an environment where we work hard, but we also make sure to have some fun along the way! At Windward Software, work-life balance is important and encouraged.

Compensation and Benefits

At our corporate office in Penticton, we offer:

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

International Locations 

Penticton, BC - Canada (Headquarters)

Chicago, IL - United States

Brisbane, QLD - Australia

Cebu City, Cebu - Philippines

Current Openings

Software Sales - Business Developer

Penticton, BC, Canada

Business Developer:  Do you thrive on challenge and have a tenacious appetite for success?  And what if you were paid well for your success?“As a Business…

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Software Sales - Sales Agent

Penticton, BC, Canada

Sales Agent:  Are you looking to be part of a successful team? Tired of feeling underappreciated?We are looking for sharp, energetic individuals to join…

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Software Sales - Business Developer

Chicago, IL, USA

Software Sales Representative(New Business)Do you thrive on challenge and have a tenacious appetite for success? And what if you were paid well for your…

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Client Services - Implementation Specialist

Toowong, QLD, Australia

Implementation Specialist:  Windward Software has an excellent opportunity open for an Implementation Specialist at our Australia office in Toowong, QLD. As…

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Windward Job Roles

These are the main type of job functions we have at Windward Software and what we look for when we do hire. Openings are posted above.

The Team Lead champions, monitors and assists the support facilitation team in their implementation, support and training activities. Continuous identification and development of new processes to improve software implementation of our business management system is a key activity, as Windward Software strives to continuously improve service to our customers.

The Team Lead conducts a significant portion of the training and user-group sessions for customers and internal staff. Therefore, they must have the ability to comfortably present complex material to both technical and non-technical users in a variety of settings: classroom, telephone, online and video.

Typically, this role is filled from within the Windward team as a career path opportunity. This is because it requires an exceptional knowledge of our business management system, including the software’s features and functionality, as well as a sound understanding of our customers’ needs.

Due to the nature of the role, travel is required to customer sites, therefore a valid passport and driver's license is required.

Key attributes:

  • Leadership
  • Analytical mind
  • Problem solver
  • Resourceful
  • Results-oriented
  • Patient
  • Self-confident
  • Project-oriented
  • Excellent communicator

Our Support Facilitators (SF) are responsible for ensuring our customers experience a smooth and successful implementation of our business management system, and that post-implementation support requirements are minimized. The SF ensures that the customer is educated in the use of the software, with the desired result being a fully satisfied customer who recognizes an improvement in their business processes after implementing Windward System Five.

This role is 80 per cent project-oriented through requirements gathering, implementation, training and support processes. Therefore, exceptional project management skills are necessary to juggle all priorities. SFs also work closely with customers on a daily basis, and liaising between them and other team members will require superior communication and follow-through skills. The remaining 20 per cent will be spent working on support queue issues with our business management system.

The SF prepares and delivers technical materials and presentations to customers and internal groups via telephone, Internet, classroom and on-site training.

Due to the nature of this position, the SF travels approximately 25 per cent of the year and will require a valid passport and driver's license.

Key attributes:

  • Analytical
  • Resourceful
  • Enthusiastic
  • Prepared
  • Self-Motivated
  • Problem-Solving
  • Follow-through abilities
  • Exceptional communicator
  • Support Facilitator - TechnicalConfidence

Windward Software offers 24/7 live global support to our customers using our business management system in more than 35 countries. We do this by hiring exceptional technical support personnel who understand the urgency and need to get a customer back up and running as quickly as possible.

Our Support Facilitators will have varying degrees of expertise ranging from troubleshooting and resolving hardware and software issues to data conversions to installations and upgrades. Accurate documentation of incoming calls, resolutions and appropriate escalation measures is vital. Given the extensive features and functionality of our business management system, the more knowledge one brings to the table in the area of business practices, the better, particularly in the area of accounting.

No two days are alike. The work is fast paced and challenging. Time is money for our customers so the ability to dig in, troubleshoot and close the ticket accurately and in a timely manner is critical.

Due to the nature of this position, we require a valid passport and driver's license.

Key attributes:

  • Customer-centric
  • Process and detail-oriented
  • Excellent communicator
  • Aptitude for problem solving
  • Persistent
  • Patient
  • Analytically minded
  • IT - SupportResourceful

Windward Software's IT Support staff members are responsible for ensuring our internal network, hardware and peripherals are operating securely, smoothly and uninterrupted. The VOIP phone system is maintained with minimum downtime, and all issues are resolved quickly and accurately. IT Support also sets up and configures equipment and systems for new staff, installs and configures software, and responds to all other internal technical issues.

As the "go-to" IT expert, up-to-date knowledge and expertise in all things IT is a must, while a passion for the challenge of troubleshooting and resolving technical issues is key.

Due to the nature of this position, and the fact that our company has staff in three other countries, our IT Support staff performs technical assistance remotely to these offices. In addition, they are expected to be on rotating emergency call status. A valid driver's license is a requirement.

Key attributes:

  • Analytical mind
  • Process and detail-oriented
  • Excellent communicator
  • Aptitude for problem solving
  • Persistent
  • Patient
  • Resourceful

Our Accounting/Finance team is responsible for the company's daily, monthly, annual accounting procedures and finance needs. With offices in three other countries, as well as our head office in Canada, the accounting and finance requirements for our business management system are vast and complex. Activities include budgeting, forecasting, analysis, reporting, maintaining internal controls and compliance. This role also requires the execution of customary tasks such as accounts payable, receivables and payroll, to name a few. Pride of ownership for work carried out on behalf of the company is essential for maintaining the best interests of Windward Software and the business management system we deliver to our clients.

Individuals with experience in these areas, plus expertise in both domestic and international finance and taxation within a software sales environment are best suited for success in this team.

Key attributes:

  • Trustworthy
  • Ethical
  • Decisive
  • Good judgment
  • Detail and fiscally oriented
  • Self-driven
  • Attention to detail
  • Budget conscious
  • Resourceful
  • Corporate confidence
  • Discreet

Our reception staff is often the first point of contact for incoming callers or visitors inquiring about our business management system. And as we all know, first impressions count! Calls are answered promptly and professionally, while carefully listening for emergencies or urgent issues to ensure these get treated quickly. Calls are transferred to appropriate staff members, or accurate messages will be taken. At Windward Software, we believe strongly that all incoming callers should speak to a live person. To ensure that all clients and potential clients worldwide receive the same service, calls are answered during the regular workday in our head office, which is on Pacific Standard Time. From then on, other Windward Software centers around the world respond to calls 24/7.

The front office is a hub of activity with a busy switchboard, arrival of guests and many other administrative tasks to be taken care of. You are the face of Windward Software and customers will "hear your smile" over the phone, and onsite visitors will see your smile and feel welcomed. The ability to juggle multiple priorities, maintain accuracy while meeting deadlines is imperative as is your honed computer and office skills. A valid drivers license is required for this role.

This position is an excellent stepping-stone to grow your career at Windward Software. It all depends on you!

Key attributes:

  • Reliable
  • Friendly
  • Personable
  • Professional
  • Exceptional communicator
  • Customer focused

Our Administrative Assistants are responsible for all administrative duties stemming from the sales of our business management system, including our international office sales. As an example, license renewals, running recurring invoices and maintenance contracts are part of the duties. The Administrative Assistant is responsible for carrying out the daily 'end of day' activities, which are an extremely important function to the company. An Administrative Assistant will be required to undertake many different projects, therefore, this person must be self-motivated, energetic and enthusiastic, with the ability to manage their time wisely and meet deadlines while maintaining accuracy in their work.

Computer literate with solid skills using various software packages is vital, as duties include working with our Windward System Five business management system, as well as using internal websites, tools and resources with advanced Excel use. The Administrative Assistant provides reception relief and assistance with reception duties.

Individuals with previous experience in customer service, administrative functions, bookkeeping or accounting are best suited for this position. Due to the nature of this role, a valid driver's license is required.

Key attributes:

  • Reliable
  • Detail-oriented
  • Professional
  • Positive attitude
  • Organized
  • Self-motivated
  • Enthusiastic
  • Energetic
  • Flexible
  • Great communicator

Our BDs are responsible for prospecting for new business, making outbound cold calls to generate sales opportunities, and build a pipeline of prospects. BDs demonstrate our business management system virtually to prospects and take them through the sales cycle.

The BD must become well versed in all aspects of our business management system, which is deep and feature-rich. The more you know about the software and about how a business operates, the better you can successfully consult with prospects, and help them understand the ROI and why Windward System Five helps them run their business more efficiently and profitably.

There are challenging monthly targets and performance measures to hit, and you will be compensated when you do.

Key attributes:

  • Tenacious
  • Thick-skinned
  • Results-oriented
  • Excellent communicator
  • Positive attitude
  • Self-learner, self-starter

AMs are responsible for generating sales revenue by selling products and services to existing customers that use the Windward System Five business management system. AMs have monthly targets to hit and are required to call on their assigned accounts each quarter to update customers on new products, features and services, as well as demonstrate their use and benefit to the business.

The AM builds and maintains strong relationships with customers and plays an important role as a consumer advocate by communicating customer issues regarding our business management system to the appropriate internal department for resolution.

Key attributes:

  • Background in sales
  • Customer service
  • Business operations
  • Exceptional communication
  • Relationship building skills
  • Self-motivated
  • Positive attitude 

Our marketing team is responsible for the development and production of promotional materials and programs that support marketing initiatives, images and branding of Windward Software and the business management system we’ve created.

Windward Software has offices in four countries, with customers in more than 35 countries (and growing). Marketing efforts need to reflect this diversity and international presence, while attracting global interest through the communication of appropriate messages that promote our brand and our business management system.

Our marketing team uses their graphic design skills and their expertise using various software packages to design and produce online presence, sales and marketing campaigns and collateral.

Key attributes:

  • Creative mind
  • Eye for design layout
  • Love of social media
  • Resourceful
  • Self-motivated
  • Solid time management

Try out Windward Business
Management Software for yourself!

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Try Windward for Free

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