Technical Documentation & Training Assistant

WinAir; London; On-site; CAD 30,000 - 60,000; Full time

Job summary

An innovative software company in Ontario is seeking a Technical Documentation and Training Assistant to support the creation of user guides and training materials. This entry-level role emphasizes collaboration and clear communication, providing an opportunity to develop skills in technical writing and instructional design. Ideal candidates will possess strong organizational skills and a passion for learning. Flexible work options and competitive benefits are offered.

Benefits

Extended healthcare

Dental insurance

RRSP matching

Flexible work schedule

Social committee events

Qualifications

• Candidates should reside in Ontario, Canada.
• Experience in a SaaS or aviation context preferred.

Responsibilities

• Support the creation and maintenance of technical documentation.
• Assist in designing training materials and delivering virtual training.
• Collaborate with SMEs to create clear content.

Skills

Exceptional written and verbal communication skills

Strong organizational and project management abilities

Ability to simplify complex technical concepts

Creativity in designing engaging content

Customer-focused mindset

Education

Diploma or degree in Technical Communication or related field

2 years of experience in technical writing or instructional design

Tools

Microsoft Suite

Adobe InDesign

SolidWorks

Composer

OBS Studio

Atlassian products (Jira and Confluence)

Job description

Job Overview

The Technical Documentation and Training Assistant will be primarily responsible for supporting the creation, organization, and maintenance of WinAirs technical documentation and training materials. They will assist in developing clear and engaging content that helps customers and team members effectively understand and use the WinAir system. Working closely with the Documentation, Training, and Support teams this individual will help ensure that all learning and reference materials are consistent, accurate and aligned with current product functionality.

This is an entry-level to intermediate position that offers an opportunity to develop skills in both technical communication and instructional design within a collaborative software environment. A passion for learning, attention to detail and strong organizational abilities will be key to success in this role. The Technical Documentation and Training Assistant may also be required to perform other related duties as assigned to support departmental and organizational objectives.

Documentation & Technical Writing

• Collaborate with subject matter experts (SMEs) to gather information and translate technical concepts into clear, concise content.
• Review and edit existing materials to ensure consistency in tone, style and formatting across all documents.
• Manage version control and documentation updates in alignment with product releases.
• Create visual aids such as flowcharts, diagrams and screenshots to enhance clarity.
• Maintain an internal knowledge base and assist with onboarding documentation.
• Ensure documentation aligns with company standards and accessibility guidelines.
• Develop and maintain comprehensive documentation including user guides, API references, release notes and training materials.

Training & Support Enablement

• Assist in designing and updating training materials including presentations, e‑learning modules and quick‑reference guides.
• Support the delivery of virtual training sessions for customers and internal staff.
• Collaborate with the Support team to identify recurring customer challenges and proactively address them through updated documentation or training.
• Apply adult learning principles and instructional‑design best practices to create engaging, effective learning experiences.
• Contribute to onboarding programs for new team members and help maintain alignment between training and support resources.

Qualifications

Education & Experience

• Diploma or degree in Technical Communication, Education, Instructional Design, Computer Science, Aviation or a related field.
• 2 years of experience in technical writing, instructional design or software training – preferably in a SaaS or aviation context.
• Proficient with Microsoft Suite, Adobe InDesign, SolidWorks, Composer and OBS Studio.

Experience with Documentation Tools and E‑Learning

• Experience working with Atlassian products (Jira and Confluence) would be beneficial but not required.

Skills & Aptitudes

• Exceptional written and verbal communication skills.
• Strong organizational and project management abilities.
• Ability to simplify complex technical concepts for diverse audiences.
• Creativity in designing engaging and interactive learning content.
• Customer‑focused mindset with a commitment to continuous improvement.

Environment & Physical

• Candidate must reside in Ontario, Canada.
• Work in a fast‑paced environment with changing priorities.
• Be able to work remotely and on‑site upon request.
• Be able to sit for prolonged periods.

Additional Information

Why Work for Us

We offer a competitive compensation package based on experience and a proven track record of success relative to the deliverables of the role. Benefits offered at WinAir include extended healthcare, dental, EAP, RRSP matching, etc.

We are also proud to offer a flexible work schedule including Summer Friday hours, maximizing good work‑life balance, different social committee events and quarterly Town Hall meetings to foster teamwork and a strong long‑lasting work relationship.

To Apply

Please submit your resume and a detailed cover letter explaining your experience, knowledge and ability towards this career path and why we need to speak with you. Thank you in advance for your interest. Only those candidates selected for an interview will be contacted. If you require any accommodation at any point of the recruitment process please let us know.

Remote Work: Yes

Employment Type: Full‑time

Key Skills

• Delivery
• Information Technology Sales
• Investment Management
• Linux Administration
• Documentation

Experience: years

Vacancy: 1