Head of Product

Toronto, ON, Canada

Full Time

Operations

Executive

Who we are

At WELLSTAR, we are committed to reshaping Canadian healthcare by leveraging technology to address the administrative burdens that pull physicians away from their true calling—patient care. Our mission is to support providers and patients, shifting the emphasis back to quality, timeliness, and positive outcomes. With a comprehensive suite of technology solutions, we have successfully helped thousands of providers adopt and benefit from modern, interoperable technologies that improve patient outcomes and system efficiency.

Whether you are in research and development, administration, communications, operations leadership, or technology, joining us now is an opportunity to play a critical role in transforming how healthcare is managed and experienced in Canada.

DoctorCare was acquired by WELLSTAR in 2020, and we now operate as part of Canada’s leading healthcare technology ecosystem, benefiting from the comprehensive resources and expertise of a company that serves over 40% of practitioners nationwide.

The opportunity

Our solution, Practice Care by DoctorCare, helps doctors optimize their medical practices by providing actionable insights and automated billing, alleviating the need to understand complex patient enrolment and funding models so they can maximize their revenue potential every month. DoctorCare also offers management and consulting services to groups of physicians under the FHO patient enrolment model.

Reporting to the Senior Director, Operations, we are hiring a Head of Product. In this senior leadership role, you will own the strategy, roadmap, and delivery of DoctorCare’s product portfolio, shaping the transition from a service-based business to a scalable, SaaS-enabled, AI-driven platform. This is a rare and rewarding opportunity to shape the future of product at DoctorCare.

You will provide direct leadership and mentorship to a Junior Product Manager, with the opportunity to expand the team as the function grows. You will be accountable for driving operational efficiency, product innovation, and business impact across the organization. This includes translating deep internal billing expertise into repeatable, productized solutions, launching and scaling the AI Billing Bot, and leading internal efficiency initiatives that streamline workflows and accelerate execution. You will balance hands-on product management with long-term strategic planning, ensuring that initiatives launched today align with a roadmap for one year or more.

This is a highly visible and collaborative role, working closely with Operations, Engineering, AI, Sales, and Customer Success teams to define requirements, prioritize initiatives, and drive execution. You will influence pricing, product packaging, and cross-sell strategies, and serve as the senior voice on product, shaping how DoctorCare evolves its technology-enabled offerings.

This is an existing, full-time opportunity with a hybrid model for candidates based in the GTA (two days per week in the Toronto office). We are also open to considering fully remote candidates within Canada.

What's in it for you?

Impact. You will lead high-priority initiatives, including the AI Billing Bot and internal efficiency projects that enhance operational productivity. Your work will directly improve customer experience, streamline workflows, and provide measurable gains for the business. You will see the impact of your decisions in real time, across internal teams and physician-facing products.

Ownership at scale. You will take ownership of a rare transformation: moving from a service-led business to a SaaS-enabled, AI-driven platform. You will build the operational engine and product infrastructure that enables DoctorCare to scale efficiently, improve margins, and reduce churn. You will have full accountability for DoctorCare’s core Billing Solutions products, including Practice Care, Billing Care, ClinicAid, and enterprise billing offerings. This is a career-defining opportunity to leave a measurable imprint on the company’s evolution.

Influence. You will define product bets, prioritize initiatives, and sequence investments to maximize long-term enterprise value. You will be the decision-maker on modernization, sunsetting, and scaling across multiple product lines. You will help establish best practices, frameworks, and reporting structures that ensure sustainable success. You will provide a clear vision for the product function and influence the broader organization’s approach to technology and operational efficiency.

Career development. This role carries significant runway for growth. As DoctorCare continues to acquire businesses and expand product lines, your scope and strategic influence will grow accordingly. You will have the opportunity to shape the organization’s product strategy at a senior level and potentially grow into a VP or Chief Product Officer-type role over time.

You will:

Lead product transformation. You will own the end-to-end product strategy and execution for DoctorCare’s Billing Solutions. This includes leading the transition from a service-heavy business to a scalable, SaaS-enabled, technology-driven platform. You will translate deep domain expertise in billing and back-office operations into repeatable, productized solutions. You will prioritize initiatives that improve margins, reduce churn, and drive operational efficiency across internal teams and customer-facing products.
Drive day-to-day product management and strategic roadmapping. You will balance hands-on execution with forward-looking strategy. This includes writing and managing tickets for the tech team, shaping product requirements, and tracking key metrics for AI initiatives such as the AI Billing Bot and internal efficiency projects. At the same time, you will maintain a roadmap with a one-year-plus horizon, ensuring alignment between short-term delivery and long-term enterprise goals.
Lead and develop your team. You will provide senior product leadership to a small but growing team, including one junior product manager. You will mentor, guide, and enable your team to deliver effectively while fostering a culture of accountability, ownership, and continuous improvement. You will ensure alignment across cross-functional partners, including Operations, Engineering, AI, Sales, and Customer Success.
Embed metrics, systems, and operating rigour. You will define success metrics, SLAs, and reporting structures for product performance. You will leverage tools such as Jira, Asana, Notion, or Monday.com to manage workflows and track execution. You will ensure internal systems and AI-enabled tools are adopted effectively, supporting faster delivery and measurable outcomes.
Collaborate to drive impact. You will work closely with executive leadership to influence pricing, product packaging, and enterprise expansion strategies. You will support operational efficiency initiatives and enable other teams to scale by providing structure, process, and technology solutions that strengthen the business.

What you bring:

The expertise. You have successfully taken SaaS products to market and driving adoption, achieving measurable business outcomes. You have proven product leadership experience, ideally driving service-to-SaaS or internal-tool-to-external-product transformations. You understand product lifecycle management, portfolio strategy, and commercial outcomes. You have experience executing roadmaps, modernizing workflows, productizing domain expertise, and embedding AI or automation to improve efficiency. You think strategically while executing relentlessly. You can navigate ambiguity while driving measurable results. Ideally, you have a background in SaaS, healthcare tech, fast-paced startups, or tech companies that leverage AI and automation to drive efficiency.
The communication and collaboration skills. You have professional written and verbal communication skills, and you can adapt your presentation style to meet the needs of nontechnical stakeholders. You are comfortable partnering with cross-functional teams to translate operational needs into product requirements, roadmaps, and scalable solutions. You can influence across functions and senior leadership, building trust and alignment in complex environments.
The team management capability. You have led small, high-leverage teams, ideally including distributed or offshore contributors. You bring commitment to coaching, accountability, and humility, and can navigate conflict or ambiguity with confidence. You can balance hands-on execution with guiding others to deliver results. You foster collaboration, mentorship, and a high-performance culture.
The technical and analytical skills. You are deeply familiar with a wide range of modern product development and management tools, including Jira, Asana, Slack, Notion, Monday.com, and analytics platforms. You can quickly adapt to new systems. You have experience leveraging technology, automation, or AI to build, drive efficiency, scale, and improve product experience.

What you can expect from our interview process:

A virtual interview with a Talent Advisor discussing your interest in the role and your experience. The conversation will be recorded using BrightHire, an AI-powered video interview tool. More details will be shared when you are invited to interview.
An in-person interview with the Senior Director, Operations and two senior team members to learn about our billing solutions and growth strategy. You will be able to share your insights and ask questions about the company and the role.
A case study, designed to give you an opportunity to demonstrate your problem-solving approach and relevant skills for the role.
An in-person meet and greet with the team.

Compensation

The salary for this position is $100K - $150K inclusive of bonuses. The salary will be determined based on several factors, including the candidate’s experience, qualifications, skills, and the needs of the organization. At WELL, 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.

Apply now.

Interested in applying but worried you don't have it all? At WELLSTAR, 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. Express your interest here.

WELLSTAR 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 upon request for candidates participating in all aspects of the selection process.

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