Desktop Support Technician jobs in Calgary, AB

Software Support Specialist

Who We Are

Kailo Medical builds workflow software that radiology and medical imaging teams depend on daily — reporting tools, system integrations, and AI products changing how imaging studies get read and reported. Our platform runs across Canada, Australia, New Zealand, North America and beyond, and it connects directly to patient care: the reports clinicians produce, how studies get prioritized, and the safe flow of data between systems.

About the Role

We're looking for a client-facing problem-solver to join our support team. You'll be the first person our clients reach when something isn't working - diagnosing issues, working across systems to find root causes, and getting clinicians and operations teams back to their work quickly.

The right person communicates well, is curious about new technology, and doesn't mind a fast-moving environment where the work varies day to day. You're comfortable trying things you haven't done before, and you collaborate easily with teammates both nearby and overseas. If solving problems for real customers energizes you, and you want your work to have a visible impact on the people using it, we'd like to talk to you.

This role is based out of our Calgary office.

What You'll Be Doing

• Fielding first-line technical support requests from clients by phone and email
• Digging into software issues with clients to understand what's going wrong and resolving them
• Logging and tracking cases through our ticketing system
• Escalating harder problems to development and QA, and flagging patterns you notice across tickets
• Helping surface bugs and following them through to a fix with the product team
• Writing and maintaining knowledge base articles so clients can help themselves
• Seeing incidents through to full resolution
• Focusing on customer satisfaction as a core measure of the job
• Keeping current on new releases, features, and support best practices

How We Work — AI-Native by Default

Use AI tools as a core part of how you work — drafting documentation, summarizing client issues, spotting patterns across tickets and accelerating troubleshooting

Help build reusable AI tools and prompts that make support faster and more consistent across the team

Own your output. AI helps you move faster, but you're accountable for accuracy - validate what it produces and apply good judgment, especially with clinical data

If you already use AI tools day to day, you'll fit right in. If you're keen to but haven't had the chance, we'll get you there fast.

What We're Looking For

• Experience in application or technical support, ideally within healthcare, radiology IT, or a related field
• Solid troubleshooting methodology and the ability to work through complex technical problems
• Comfort across Windows, macOS and Linux, plus general IT/networking knowledge
• Experience with ticketing systems and remote support tools
• Strong written and verbal communication - including translating technical detail for non-technical audiences
• A genuine drive to help people and a customer-first mindset
• Ability to work both independently and as part of a distributed, global team
• Good organizational and time-management instincts
• Interest in healthcare/MedTech and in improving how medical imaging workflows function
• Legal right to work in Canada

Bonus Points For

• Knowledge of HL7, DICOM and FHIR
• Hands-on experience with RIS/PACS or other clinical imaging systems, and an understanding of radiology and medical imaging workflows
• Experience with SQL, scripting or basic programming
• Familiarity with Zendesk or similar ticketing management tools
• Familiarity with Zabbix/Grafana server monitoring tools, or similar
• Familiarity with physical, virtual and cloud servers and technologies

How You'll Grow Here

• First 30 days: Up to speed on our products, customers, and support workflows, and already contributing to live tickets
• First 90 days: Resolving and escalating issues independently, confident across the product suite, and a dependable part of the support rotation
• By 6 months: A go-to specialist — handling complex incidents, sharpening how the team troubleshoots and documents, and raising the bar for support overall

You'll Fit Right In If

You're genuinely curious about how our clients work and why

You ask good questions and listen carefully to the answers

You communicate clearly and keep clients and colleagues aligned

You're organized and bring structure to ambiguity

You enjoy working with new technology and aren't afraid to try new things

You care that the software actually helps the clinicians and teams using it

Also Required

Relevant tertiary qualification in Information Technology or a related field (or equivalent demonstrated experience)

Pay: From $60,000.00 per year

Benefits:

• Dental care
• On-site gym
• Work from home

Licence/Certification:

• Driving Licence (required)

Willingness to travel:

• 25% (preferred)

Work Location: Hybrid remote in Calgary, AB