Tier 1 Technical Support Analyst

Who we are

OSCAR Pro, a leading Electronic Medical Records (EMR) platform in Canada, is part of the WELL Health Technologies family. Initially developed by McMaster University’s Department of Family Medicine, OSCAR Pro was built on a foundation of collaboration to improve healthcare delivery and patient outcomes. We have integrated innovations from various OSCAR service providers to offer a robust, secure, and versatile solution tailored to the diverse needs of clinics of all sizes.

Our platform empowers healthcare providers by streamlining administrative tasks, enhancing clinic efficiency, and enabling more time for patient care. With features like digital patient engagement, secure messaging, and seamless integration with other healthcare systems, OSCAR Pro reduces the administrative burden on clinics and improves the overall patient experience.

Our mission is to empower practitioners to deliver high-quality care while spending less time on administration. By providing cutting-edge digital tools, we ensure that healthcare professionals can focus on what truly matters—improving patient outcomes and experiences.

Who we need

Reporting to the Team Lead, we are seeking a Tier 1 Technical Support Analyst who is motivated by the opportunity to make a meaningful contribution to healthcare technology. You will provide front-line assistance to healthcare professionals, helping them resolve technical issues, improve their workflows, and fully leverage our software to deliver better patient care. You will also collaborate with internal teams to strengthen support processes, enhance documentation, and contribute to the overall reliability and effectiveness of our platform.

This is an existing, 1 year contract remote opportunity open to candidates across Canada, with the exception of Quebec due to provincial employment requirements. Shift hours are 8:00 AM to 5:00 PM Eastern Standard Time.

What’s in it for you

Impact. By ensuring healthcare professionals can efficiently use our platform, you will directly impact how they deliver patient care. Your support will help reduce administrative burdens, allowing clinics to focus on what matters most—improving patient outcomes.

Technical challenges and exposure. You will gain valuable exposure to healthcare systems, electronic medical records, and billing processes such as OHIP and BCP, while building technical expertise in software support and system administration.

Career growth. You will join WELL Health, a leading Canadian digital health company that operates and owns outpatient medical clinics while also delivering a broad suite of technology and telehealth solutions. This Tier 1 support role offers a clear progression path to Tier 2 and Tier 3 support or other teams, such as onboarding, training, and implementation.

As our new Technical Support Specialist, you will focus on:

• Support. You will help healthcare professionals apply the software effectively in their daily work, ensuring they achieve maximum value from the platform. You will provide phone and ticket-based support to healthcare providers and clinics using the EMR system, guiding users through product features, troubleshooting issues, and ensuring timely resolution.
• Documentation. You will create and maintain clear, accurate, and user-friendly guides for both customers and internal teams.
• Process improvement. You will partner with internal teams on projects, escalate issues when required, and share insights to prevent recurring problems. You will identify opportunities to improve workflows, reduce friction for customers, and enhance the overall support experience.

You bring:

• The customer focus. You are motivated to support healthcare professionals and can clearly and patiently explain technical concepts. You approach every interaction with professionalism, empathy, and a strong commitment to service.
• The technical experience. You have customer service, call centre, or technical support experience. You possess technical aptitude and are comfortable working with software, as well as independently troubleshooting issues and researching solutions.
• The problem-solving skills. You are analytical and resourceful, with the ability to isolate, define, and resolve technical issues efficiently. You apply structure and rigour to your work, balancing accuracy with timely delivery.
• The growth mindset. You are adaptable and eager to expand your technical skills. You stay engaged in dynamic environments with evolving customer needs and are committed to continuous learning.
• The professionalism. You have strong written and verbal communication skills, meticulous attention to detail in documentation, and a respect for compliance and privacy standards in healthcare technology.

Join us in revolutionizing healthcare through technology.

As a scaling company backed by WELL Health Technologies, we are expanding rapidly across the country. At OSCAR Pro, we are driven by a passion to make a lasting impact on the healthcare system. Our team is dedicated to building resilient, compliant, and easy-to-use technology that transforms how care is delivered.

Transformation starts with a strong team.

We believe that empowering our team members is critical to success. At OSCAR Pro, we foster a culture of respect where every individual feels valued, included, and supported to reach their full potential. Our workplace embraces diversity and prioritizes the well-being of our team and the communities we serve.

We offer a remote-first work environment, opportunities for growth within OSCAR Pro or across the broader WELL Health Technologies Group, and a supportive culture that balances professional success with personal well-being. Whether you are driving projects that shape the future of healthcare or focusing on your development, we are here to support you.

At OSCAR Pro, your ideas can make a real difference—not just in our organization but in the lives of patients and healthcare providers across Canada.

Apply now

Interested in applying but worried you don't have it all? We know not everyone gains their experience following a traditional path. If you share our values, want to make a difference in healthcare technology solutions, and meet 70% of the qualifications, we encourage you to apply.

What you can expect from our interview process:

• A virtual interview with a Talent Advisor discussing your interest in the role. The conversation will be recorded using BrightHire, an AI-powered video interview tool. More details will be shared when you are invited to interview.
• A final virtual interview with the Team Lead and Director, Customer Support. You will have the opportunity to learn more about the role and team as well as ask any final questions.

The salary for this position is $55,000. At OSCAR Pro, we are committed to fair and equitable compensation and aim to provide a competitive salary that reflects the value and expertise of the successful candidate.

OSCAR Pro is committed to fostering a diverse, inclusive, and accessible workplace. We welcome and celebrate the diversity of applicants and team members across ability, race, gender identity, sexual orientation, and lived experience. We strive to create an environment where differences are valued and contribute to our collective success.

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