Customer Education Specialist

About Club Caddie:

Club Caddie is a rapidly growing technology company that builds cloud-based golf course management software (GMS). Club Caddie was acquired by Jonas Software, a global leader serving 40,000+ customers in 15+ countries. Jonas Software is a 100% owned subsidiary of Constellation Software Inc. (CSU.TO), headquartered in Toronto. 

We serve public, semi-private, single-course operators (SCOs) and multi-course operators (MCOs). Our customers are general managers, pro shop staff, food and beverage teams and course operators — people busy running a golf business, not studying software. Our job in Education is to make the software easy to learn and easy to keep up with. 

Role Overview 

The Customer Education Specialist helps produce and maintain training materials that teach Club Caddie customers how to use the software. 

This is a hands-on content production role. You will turn product releases, customer questions and support trends into knowledge base articles, LMS lessons, in-app guidance, training scripts, walkthrough videos and webinar follow-up material — and keep that library accurate as the product changes. 

You will work directly with the Head of Education, who sets the priorities, the content standards and the approvals. You own the deliverables, the production schedule and the accuracy of what you prepare. Content is published through our established review and approval process, and system access is granted by role. As you demonstrate accuracy, you will take on more of the recurring production work independently. 

Key Responsibilities:

Knowledge base articles. Draft, edit, and update articles in Club Caddie’s structure and voice, and prepare them for publication. Keep screenshots, steps, and terminology matched to what customers actually see. 

LMS courses and lessons. Build and maintain lessons, quizzes and learning paths in Club Caddie University. Keep courses current after releases and correct outdated material. 

In-app guidance. Build and maintain Whatfix flows — walkthroughs, tooltips, launchers and announcements — using established patterns. Test them before they go live and correct them when the interface changes. 

Training scripts and walkthrough videos. Review camera-ready scripts for software walkthroughs. Record clean screen captures with narration, handle basic editing, captions and titles, and prepare files for review. 

Webinar recordings and follow-up material. Access the Zoom recording after a session, download and lightly edit it, add captions or titles, prepare it for the Club Caddie webinar page, and confirm the video and links work. Turn webinar content into articles, clips, lessons and summaries. You will not be the primary presenter. 

Release-related updates. Read release notes, tickets and recordings to understand what changed and who it affects. Work with the Head of Education to decide what each customer-facing release needs — an article, a lesson, a video, an in-app flow, or nothing — and produce it. 

Trackers and basic reporting. Maintain the production and content-health trackers, pull LMS, knowledge base and webinar data into existing reports on a set schedule, and flag anything that looks wrong. 

Required Qualifications: 

• Strong written English, with the ability to explain a technical process in plain, direct steps 

• Clear instructional and technical writing — a portfolio or writing samples will be requested 

• Experience creating customer-facing education for a software product 

• Ability to learn unfamiliar software quickly from written sources and recordings 

• Basic video editing — trimming, captions, titles, exporting 

• Strong organization and follow-through across several projects at once 

• Reliable remote communication, with clear written updates 

• Comfort working inside an established voice, template and approval process 

• Responsible use of approved AI tools, including verifying output against a source before it moves forward 

Preferred Qualifications:

These are helpful but teachable. Do not rule yourself out if you have not used them. 

• Whatfix or another digital adoption platform (WalkMe, Pendo, Appcues) 

• HubSpot Knowledge Base or a comparable knowledge base platform 

• TutorLMS, WordPress, or another LMS 

• Camtasia, Descript or comparable video tools 

• AI voice or synthetic narration tools 

• Golf course operations, hospitality technology or point-of-sale systems 

• Club Caddie product knowledge 

Tools you will use: HubSpot Knowledge Base · Club Caddie University (TutorLMS on WordPress) · Whatfix · Camtasia · ElevenLabs · YouTube · Zoom · Notion · Google Workspace 

Schedule: 

This role requires a daily collaboration window of 8:00 a.m.–1:00 p.m. Pacific Time (11:00 a.m.–4:00 p.m. Eastern Time), Monday through Friday. This is when reviews, questions, working sessions and any live support happen. 

The schedule follows the U.S. clock, so your local working hours will shift by one hour when U.S. daylight saving time begins and ends each year. 

What Success Looks Like:

First 30 days — you know the product well enough to write about it, have drafted your first article and script, and understand our standards and approval process. 

By 90 days — you produce articles and lesson updates on a regular cadence with light review, and have supported the education work for at least one customer-facing release. 

By 6 months — you run the release-to-content workflow for standard releases with review rather than direction, and content maintenance runs on a schedule instead of in reaction. 

By 12 months — you carry full categories of content end to end within the approval process, and the Head of Education spends less time producing and more time on strategy and measurement. 

Why Club Caddie? 

• Work on education that customers use every day to run real businesses 

• Own visible deliverables from the start, in a function that is actively being built out 

• Learn a complete customer education stack — knowledge base, LMS, in-app guidance, video and webinars — in one role 

• Work directly with the Head of Education, with real ownership of what you produce 

• Join a fast-growing SaaS company backed by Jonas Software and Constellation Software Inc.