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 President, we are hiring a Director of Implementation to join our team. In this newly created role, you will be part of the Senior leadership team at OSCAR Pro as we continue to scale. As the new Director of Implementation, you will drive a culture of continuous improvement by enhancing processes, automating onboarding and training where feasible, and identifying opportunities to deliver a customer-first experience. Your strategic approach will ensure that every aspect of implementation aligns with our commitment to excellence. You will lead the migrations, onboarding and training teams.

This is a remote role based anywhere in Canada.

What's in it for you

• Impact. You will play a crucial role in helping healthcare providers onboard OSCAR Pro and leverage the system to deliver better patient care by improving efficiency in busy practices - enabling them to spend more time with their patients and less time on admin. Your work will go beyond just meeting client needs. You will be making a tangible difference in the healthcare industry that ultimately helps improve patient health outcomes.
• Flexibility and influence. You will be part of a collaborative and inclusive culture where every contribution is valued. Your ideas and insights will help shape our services, drive continuous improvement, and meet the evolving needs of our clients. You will develop and execute on a cohesive, improved onboarding, implementation and training process by proposing solutions, driving automation, and influencing how we support our clients.
• Growth and career development. You want to grow—your skills, your career, and your impact. We offer you the opportunity to advance within OSCAR Pro or across other businesses within the WELL Health Group. You will work closely with squads—cross-functional groups of business leaders—gaining exposure and contributing to initiatives spanning multiple business units. This experience will broaden your organizational insights and open new pathways for career advancement.

How you will make an impact:

• Lead and develop teams. You will manage and mentor managers overseeing training, onboarding, and data migration and fostering a culture of continuous improvement. You will provide coaching to enhance team knowledge, support daily tasks as needed and drive operational efficiency.
• Drive process enhancements. You will actively engage with the team, shadowing processes to identify areas for improvement. You will analyze current practices, identify opportunities for automation, and implement lean methodologies to accelerate implementation timelines and reduce onboarding wait times. You will use data-driven approaches to continuously refine onboarding, training, and data migration processes.
• Customize customer journeys. You will develop tiered onboarding and training programs tailored to customer needs, ranging from self-service options to fully supported experiences.
• Oversee data migration and technical processes. You will oversee data migration as needed, leveraging your understanding of EMR databases, data conversion, and related challenges to provide solutions to streamline the process for clients.
• Collaborate with stakeholders. You will partner with internal teams and clients to understand their needs, gather feedback, and drive ongoing improvements. You will foster a transparent approach to problem-solving, focusing on rapid iterations to optimize outcomes.

What you bring:

• The experience. You bring a customer-focused mindset, dedicated to understanding and meeting client needs with personalized solutions. With a strong background in system implementations and integrations, you have lead implementation teams either within EMR systems or healthcare technology, from the provider or client side. You possess a solid understanding of EMR databases, data conversion, and privacy considerations.
• The leadership skills. As a proven leader, you have a track record of motivating and guiding teams fostering an environment where members execute efficiently and think proactively. Your ability to foster a results-oriented culture ensures that your team not only meets but exceeds expectations, contributing significantly to client satisfaction. You lead by example, demonstrating autonomy and problem-solving prowess.
• The strategic execution. You balance long-term planning with immediate action, continuously seeking opportunities for improvement. You approach process improvement holistically, mapping out systems to optimize performance. As a hands-on leader, you combine relationship-building skills with a passion for connecting people and technology to improve efficiency and productivity.
• The interpersonal skills. You have outstanding professional written, verbal, and presentation skills. You take a collaborative approach, offer meaningful insights, and can lead by example. You have exceptional communication skills, and you are an active listener. You can translate complex technical details to a non-technical audience. You genuinely appreciate diverse experiences and backgrounds and are interested in understanding others, hearing their perspectives, and addressing their concerns.
• The growth mindset. You are naturally curious, driven to research answers, and open to feedback. You acknowledge your mistakes and can adapt to setbacks. You are resourceful and can use new knowledge to solve problems. You are passionate about staying current with the latest tools and best practices. You keep your promises, take your commitments to others seriously, and have demonstrable integrity.

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 to discuss your experience and interest in the role.
• A virtual interview with the President to learn more about the company mission and vision.
• A final interview with members of the leadership team. You will be given a case study exercise to prepare ahead of the interview and will have the opportunity to share it with the leadership team and answer any questions they may have. This will also provide you with an opportunity to meet your peers and learn more about why they love working here.

OSCAR Pro is committed to supporting 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 perspective. We strive to create an inclusive workplace where differences are celebrated and fuel our success! Accommodations are available on request for candidates taking part in all aspects of the selection process.

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