Director of Customer Operations

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 Director of Customer Operations, Billing Solutions.

In this senior operational leader role, you will be responsible for owning and scaling the day-to-day performance of our Billing and Back Office functions across the organization.

You will oversee Client Success, Customer Support and Service Delivery, with a particular focus on Service Delivery, our largest operational group.

You will lead managers, execute a planned organizational restructure, and embed disciplined KPI and SLA governance across all operational teams.

You will bring clarity to decision rights, consistency to operating rhythms, and measurable accountability to a function central to both customer experience and financial performance.

This is a highly visible and collaborative position.

You will partner closely with Product, Technology, Sales, Marketing, and Finance to translate operational needs into system improvements, align resources with growth priorities, and strengthen the end-to-end customer journey.

You will establish the reporting structure, performance metrics, and operating cadence required to manage customer satisfaction, billing performance, retention, and service delivery excellence.

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.

DoctorCare is evolving from a predominantly service-based model to a more scalable, SaaS-enabled, technology-driven organization.

This role sits at the center of this transformational shift.

You will modernize workflows, introduce automation and AI-enabled processes, improve cost efficiency, and ensure operational readiness for new and expanding SaaS offerings.

Ownership at scale.

You will lead a full reorganization from product-based task ownership to clearly defined service-delivery, customer-success, and client-support lines.

You will shape team structures, clarify accountability, and design a service model built for growth and efficiency.

Strategic influence.

You will collaborate directly with Product, Technology, and executive leadership to align operational priorities with company strategy.

You will influence roadmap decisions, resource planning, and cross-functional initiatives.

Your work will directly improve customer experience, reduce cost-to-serve, strengthen billing performance, and enhance scalability.

Career development.

We are seeking a leader who thrives in environments undergoing meaningful change.

You are motivated by ownership, accountability, and continuous improvement.

This role has a clear runway for expanded scope and senior leadership responsibility as we continue to grow through acquisitions and expansion.

You will: Lead operational performance.

You will own the performance and outcomes of Client Success, Customer Support, Service Delivery, and Billing & Back Office operations.

You will establish clear decision rights, performance standards, and accountability across all teams.

You will build structured operating cadences, including weekly and monthly reviews, to track results and drive disciplined execution.

You will document and strengthen operational processes to ensure appropriate controls, compliance, and consistency.

You will rely on subject-matter experts for detailed billing and regulatory expertise while maintaining executive-level accountability for outcomes.

Develop leaders.

You will lead and develop a management team of three to four direct reports, with accountability for approximately fifty onshore employees and close collaboration with an offshore team of approximately twenty.

You will coach managers to elevate performance standards, strengthen decision-making, and foster ownership within their teams.

You will create a culture of operational rigour, measurable accountability, and continuous improvement.

You will build engagement, reduce attrition, and ensure teams are fully enabled to perform at a high level.

Drive organizational design and change.

You will lead an organizational redesign across Client Success, Customer Support, and Service Delivery.

You will partner with senior leadership to implement structural changes effectively, incorporating operational insight and team feedback where appropriate.

You will lead structured transition plans, communicate changes clearly and consistently, and maintain a visible leadership presence throughout.

You will assume full authority over team design, role clarity, and performance management during and after the transition.

Own metrics and performance management.

You will define, implement, and own core KPIs, SLAs, and OKRs across all operational functions.

You will ensure managers consistently review performance data and take timely corrective action.

You will maintain high standards for customer outcomes, including NPS, CSAT, retention, and service responsiveness.

You will establish measurable progress in reducing cost-to-serve while improving scalability and service quality.

Lead SaaS transformation and tool adoption.

You will play a central role in transitioning operations from service-heavy workflows to more productized and automated models.

You will drive adoption and disciplined use of core systems, including CRM, ticketing platforms, automation tools, and AI-enabled workflows.

You will partner with Product and Technology to translate operational needs into structured product requirements.

You will prioritize initiatives that enhance scalability, improve efficiency, and lower cost-to-serve.

Plan workforce and financial performance.

You will partner with Finance and senior leadership on workforce planning, productivity initiatives, and headcount modelling.

You will develop clear business cases for new roles or structural changes.

You will actively improve wage cost as a percentage of revenue by redesigning processes, optimizing tooling, and refining team structure.

You will align resource allocation with growth objectives and operational targets.

Collaborate to enable revenue growth.

You will work closely with Sales and Marketing to support customer engagement, onboarding, retention, and cross-sell initiatives.

You will ensure operational readiness to support revenue expansion and seamless customer experience.

You will collaborate across the organization to remove friction, streamline workflows, and improve internal efficiency.

You will cultivate a culture of learning and optimization, ensuring strong system adoption, high engagement, and sustained operational excellence.

What you bring: The expertise.

You have proven leadership experience in operations, service delivery, or customer-facing roles, managing managers, and overseeing multi-layered, distributed teams.

You have successfully driven organizational change within growing or transforming environments, translating strategic direction into clear structures, decision rights, and measurable outcomes.

You have defined and operationalized KPIs, SLAs, and structured operating rhythms that drive accountability and performance. The transformation project experience.

You have led operational modernization initiatives, transitioning teams from service-heavy or manual workflows to scalable, productized, and technology-enabled models.

You are comfortable driving the adoption of core systems, including CRM platforms, ticketing tools, automation solutions, and AI-enabled workflows.

You can partner effectively with Product and Technology teams to translate operational needs into requirements and roadmaps.

You approach systems and process design with a focus on scalability, compliance, and long-term efficiency.

The leadership skills.

You have a proven ability to build and foster collaborative relationships at any level.

You have exceptional communication skills.

You are adept at stakeholder management and can influence across functions, including Sales, Marketing, Finance, Product, and Technology.

You have experience leading change management and maintaining credibility with senior leadership, fostering an environment of trust and respect.

You approach challenges with composure and accountability. The team management skills.

You have experience leading and managing large teams, guiding work, evaluating performance, and providing career development support.

You can navigate conflict and remove barriers.

You foster a disciplined, performance-oriented culture grounded in accountability, collaboration, and continuous improvement, while sustaining high engagement and low attrition.

You have experience working with offshore or distributed teams, or outsourced teams and managing third-party vendors.

The technical skills.

You are highly analytical and can confidently work with performance data to forecast demand, model headcount, assess productivity, and inform strategic decisions.

You use data to identify root causes, define corrective actions, and track measurable progress.

You are proficient with Microsoft Office and demonstrate the ability to quickly master operational systems, including CRM, EMR, and SaaS platforms.

You bring a structured approach to reporting, planning, and operational review processes.

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 WELLSTAR, 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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