Chief of Staff

Remote

Full Time

Office of the CEO

Executive

Who we are

WELL is an innovative technology-enabled healthcare company whose overarching objective is to positively impact health outcomes by leveraging technology to empower and support healthcare practitioners and their patients.

WELL's practitioner enablement platform includes comprehensive end-to-end practice management tools, including virtual care and digital patient engagement capabilities, Electronic Medical Records (EMR), data protection services, and Revenue Cycle Management (RCM) through our DoctorCare solution.

WELL owns and operates Canada's largest network of outpatient medical clinics serving primary and specialized healthcare services and is the provider of a leading multi-national, multi-disciplinary telehealth offering.

The opportunity

Reporting to the CEO, we are looking for a Chief of Staff to the CEO. As Chief of Staff, you will serve as a trusted partner and amplifier of the CEO’s impact, ensuring that priorities move from decision to execution. You will bring leverage to both daily operations and long-term initiatives, acting as the connective tissue between the CEO, the executive team, and the broader business. You will play a central role in driving the execution of priorities and OKRs, improving organizational efficiency, and freeing CEO bandwidth during a period of high growth and IPO preparation.

This is a hybrid opportunity based anywhere in Canada, preferably Vancouver, requiring occasional travel to Vancouver and Toronto to attend in-office leadership and strategy sessions.

Who you are

You are a highly motivated operator with experience in strategy, operations, or consulting, and an ambition to step into a future VP or GM role. You bring experience from consulting, investment banking, or strategy/operations in tech. You thrive in fast-paced, high-growth environments, are comfortable working directly with executives and boards, and excel at turning complex discussions into clear, actionable next steps. You are humble, adaptable, and motivated by impact rather than spotlight. You understand the importance of working behind the scenes to accelerate execution and multiply leadership effectiveness. You are detail-oriented yet strategic, equally capable of managing meeting follow-ups as you are of contributing to market entry strategies, acquisitions, or investor conversations. Most importantly, you are driven by the opportunity to maximize executive effectiveness and accelerate company-wide impact.

What’s in it for you

Impact. You will work side by side with the CEO, ensuring that priorities are tracked, followed through, and delivered. You will be responsible for building systems to align the organization around OKRs, ensuring that commitments translate into execution and measurable progress. You will directly influence how effectively the leadership team executes, freeing up the CEO to focus on growth, external partnerships, and long-term vision.

Executive visibility. You will become a proxy for the CEO in selected forums, building trust as an extension of his perspective and serving as the bridge between strategy and execution. You will gain direct exposure to board-level discussions, investor relations, strategic initiatives, and cross-functional decision-making. You will not only support but also actively shape how priorities are set and communicated across the organization.

Career growth. You will be positioned for continued growth, whether that means stepping into a future executive leadership role such as VP or GM, or deepening your expertise as a long-term Chief of Staff. By internalizing the CEO’s decision-making approach and building credibility across the business, you will develop the skillset and relationships to excel in whichever path you choose.

You will focus on:

Build and nurture relationships. You will build context and trust by shadowing the CEO, capturing follow-ups and commitments, and fostering relationships with the executive team. You will recommend early improvements to meeting prep and post-meeting alignment, delivering weekly briefings that consolidate open action items.
Executive leverage and follow-through. You will attend the CEO’s meetings, document decisions, track action items, and ensure stakeholders follow through. You will build and manage systems to track OKRs and ensure execution against CEO priorities. You will create structure and systems to maximize the CEO’s time and impact.
Operational excellence. You will prepare materials and agendas for board meetings, offsites, and investor discussions. You will optimize and implement systems to monitor execution against company priorities, surfacing risks early and ensuring alignment across the leadership team. You will establish critical processes that enable us to scale and ensure alignment against priorities, risks, and dependencies.
Strategic initiatives. You will partner with the CEO on high-impact projects such as new market entry, acquisitions, and product launches. You will synthesize insights into recommendations, helping shape how strategy is executed across functions.
Leadership development. Over time, you will internalize the CEO’s decision-making lens and serve as a trusted proxy in select forums. You will develop credibility as an extension of the CEO, building alignment and momentum across the organization.

Here’s what you bring:

The operational discipline. You have extensive experience in strategy, operations, consulting, investment banking, or similar high-performance environments. You are highly organized and skilled at turning complexity into clarity. You may have experience in SaaS or regulated industries, with exposure to board reporting, investor relations, or executive-level decision-making.
The strategic thinking. You bring the ability to step back, see the big picture, and connect daily execution to long-term company goals. You are energized by supporting initiatives that shape the future of the business. You are skilled at connecting CEO priorities to OKRs and ensuring measurable execution.
The interpersonal skills. You can build trust quickly with senior stakeholders, boards, and investors. You have exceptional written and verbal communication skills, with the ability to synthesize and present information clearly.
The drive. You have the ambition to step into a senior leadership role in the future. You thrive in high-accountability environments and are motivated by the opportunity to accelerate your career path. You are humble, adaptable, and focused on multiplying leadership impact rather than seeking the spotlight.

Why join us?

Healthcare is our sector, and we know that for WELL to be a winning team, we must provide an open environment to prioritize health and wellbeing and multiple resources to discuss mental, physical, and psychological needs openly. From the CEO to the newest hire, everyone comes together as part of our culture of respect, openness, support, and communication. We unite to empower each other to be the best we can be.

We recognize that the best way to serve our diverse patient communities is by reflecting that diversity. With almost 65% of our team members identifying as female and 70% of our leadership identifying as a visible minority, we are proud of our diverse, equitable and inclusive organization.

What you can expect from our interview process:

A virtual interview with a Talent Advisor discussing your interest in the role and the company.
An in-person interview with the VP, Growth Operations to learn about our solutions and growth strategy.
An in-person interview with the CEO. This conversation will provide deeper insights into how you will work together, insights into your future collaborators, and opportunities for career development and growth.
A case study to demonstrate your strategic thinking and adaptability.

Apply now.

Interested in applying but worried you don't have it all? At WELL, 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.

WELL 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 – this is the WELL Way! Accommodations are available on request for candidates taking part in all aspects of the selection process.

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We want anyone, anywhere to have the same chance and opportunity to build a life they love and that they are proud of. We are proactive in creating a belonging environment that anyone can be a part of. Thoughtful, data-driven decision-making is core to this success. We ask these questions to strengthen our practices by using data to identify and mitigate unconscious bias in our hiring process.

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