Medical Transcriptionist, Remote jobs in Calgary, AB

Software Support Specialist

Who We Are

Kailo Medical builds the workflow software that radiology and medical imaging teams rely on every day — reporting, integration, and the AI products that are reshaping how imaging gets read and reported. Our platform spans Canada, Australia, New Zealand, North America and beyond, and our software touches real patient care: the reports clinicians write, the studies they prioritize, the data that flows safely between systems.

The Opportunity

This is a client-facing role for someone who thrives on solving problems and helping people. You'll be the first point of contact for our clients when they need support — diagnosing software issues, troubleshooting across systems, and getting clinicians and operational teams back to what matters.

It suits someone who communicates clearly, enjoys working with new technology, and is comfortable in a fast-paced environment where no two days look the same. You're not afraid to try new things or step into the unknown, and you work well as part of a team — both locally and globally. If you're energized by customer interaction and want your work to make a tangible difference to the people using the software, this is for you.

This role is based out of our Calgary office.

Your Day to Day

Provide first-line technical support to clients via phone and email for software-related issues

Troubleshoot and diagnose software problems, working closely with clients to understand their issues and provide effective solutions

Document, track and manage customer inquiries and issues using our ticketing system

Collaborate with internal development and QA teams to escalate unresolved or complex issues, and provide feedback on recurring problems

Help identify software bugs and work with the product teams to ensure timely fixes and updates

Create and update knowledge base articles and user guides to empower clients with self-help resources

Manage technical problems and incidents through to resolution

Deliver exceptional customer service with a focus on improving customer satisfaction

Stay up to date with software updates, new features and industry 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 You'll Bring

Proven experience in application support or a similar technical support role, ideally in healthcare/radiology IT or a related industry

A solid grasp of support and troubleshooting methodologies, with strong problem-solving ability to work through complex technical issues

General IT and networking skills, with proficiency across common operating systems (Windows, macOS, Linux) and software applications

Familiarity with ticketing systems and remote support tools

Outstanding written and verbal communication, with the ability to explain technical concepts to non-technical users

A customer-centric attitude and a genuine passion for helping people

The ability to work independently and as part of a team — locally and globally — in a fast-paced, dynamic environment

Strong organizational and time-management skills

A passion for working in the healthcare and MedTech space, and for contributing to advancing medical imaging workflows

Must have current 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

Your First Six Months

30 days — Onboarded, familiar with our products, customers and support processes, and contributing to live ticket work

90 days — Independently resolving and escalating issues, comfortable across our product suite, and a reliable contributor to the support roster

6 months — A trusted specialist: handling complex incidents, improving how we troubleshoot and document, and helping raise the standard of support across the team

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: $60,000.00-$100,000.00 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