CYBERWELL brings together the expertise and legacy of trusted brands Source44, Cycura, Seekintoo and Proack, backed by WELL Health Technologies. We have deliberately united expert capabilities across proactive defense, offensive security, governance and risk, and technology solutions to support clients in all areas of their cybersecurity program. In today’s threat landscape, complexity is the constant. At CYBERWELL, we are built to help organizations not just keep up
- but get ahead. CYBERWELL is a cybersecurity company purpose-built for scale, change, and the realities of modern enterprise. We deliver cybersecurity through an integrated, risk-informed operating model that spans the full cybersecurity lifecycle
- from offensive security exposure management to GRC, architecture and engineering, threat intelligence, and 24/7 managed detection and response. We partner with enterprise leaders who are navigating regulatory pressure, evolving risk, and growing infrastructure. Whether it's a healthcare provider safeguarding patient data, a government agency defending critical systems, or a tech or financial firm scaling securely
- our team helps unify strategy, reduce complexity, and strengthen cyber resilience. Why it matters: Cybersecurity isn't just a technical issue
- it’s a business imperative. From compliance and operational uptime to reputation and trust, we help organizations protect what matters most, stay ahead of threats, and build the foundation for long-term success. Our programs improve visibility, strengthen resilience and connect security priorities to measurable business outcomes. Who we need

Reporting to the Chief Executive Officer, we are hiring a Vice President, Sales & Marketing to lead CYBERWELL’s commercial organization through its next phase of growth.



As a member of the executive leadership team, you will bring together sales and marketing capabilities across acquired businesses, establish a cohesive go-to-market strategy, and build the structure and discipline needed to scale. You will strengthen pipeline generation, elevate sales execution, and lead the pursuit of larger, more complex enterprise opportunities, positioning CYBERWELL to deliver predictable, profitable growth. This is a hands‑on executive role that combines strategic leadership with direct involvement in key deals, customer relationships, and team development. This is a Canada-based role, open to candidates across the country, with a preference for Ontario. Travel within Canada is expected approximately 50% of the time, depending on your location. Who you are

You are a commercially minded technology sales leader who knows how to turn growth ambitions into results. You have built and developed high-performing B2B sales teams, strengthened go-to-market strategies, and led complex enterprise sales in competitive markets. You bring the commercial judgment to identify new opportunities, the operational discipline to build a predictable sales pipeline, and the leadership skills to bring people together around shared goals. Comfortable navigating change and working across technical and business teams, you can connect cybersecurity capabilities to customer priorities and business outcomes.



You balance strategic thinking with a hands‑on approach, lead with accountability, and know how to build the relationships, processes, and team capabilities needed to support sustainable growth. What’s in it for you

The opportunity to build and lead. You will take ownership of shaping the next chapter of CYBERWELL’s commercial organization, bringing together sales teams and capabilities from three acquired businesses into one cohesive, high‑performing team. You will have the autonomy to assess what is working, introduce new approaches, develop talent, and establish the structure, processes, and accountability needed to support sustainable growth. This is an opportunity to build a sales organization that delivers results today while creating the foundation for long‑term success. Executive influence and ownership. As a member of the executive leadership team, you will work directly with the CEO and fellow leaders to shape commercial strategy, influence investment decisions, and identify new opportunities for growth. You will have ownership of sales and marketing performance, with the ability to turn your ideas into action and see the direct impact of your decisions on the business. The chance to drive meaningful growth. You will lead CYBERWELL’s shift toward larger, more strategic customer opportunities, working directly with sales teams, partners, and customers to pursue complex deals and build lasting relationships. You will combine your industry knowledge and commercial expertise with CYBERWELL’s technical capabilities to strengthen its market position, expand its customer base, and create new revenue opportunities across Canada. As our recent Vice President, Sales & Marketing, you will

Lead commercial strategy a

📌 Vice President, Sales (Winnipeg)
🏢 CYBERWELL
📍 Winnipeg