About us

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 new Vice President, Sales & Marketing, you will

Lead commercial strategy and growth. You will develop and execute a national sales and marketing strategy aligned with CYBERWELL’s business objectives. You will identify priority markets, target customers, and growth opportunities, with a focus on pursuing larger, more complex deals, expanding recurring revenue, and delivering predictable, profitable growth.
Build and develop a high-performing team. You will assess the existing sales organization, identify opportunities to strengthen capabilities, and build a cohesive team across sales, marketing, enablement, and partnerships. You will recruit, coach, and develop talent, establish clear performance expectations, and create a culture of accountability, collaboration, and continuous improvement.
Drive sales execution. You will work directly with your team in the field, supporting account planning, customer engagement, and strategic opportunities from initial prospecting through negotiation and close. You will provide hands-on coaching, remove barriers, and help advance complex deals while strengthening relationships with senior decision-makers and key customers.
Establish sales processes and discipline. You will introduce and refine consistent sales methodologies, qualification criteria, pipeline reviews, and forecasting practices. You will leverage Salesforce as the central source of commercial information, improving data quality, visibility, and accountability while streamlining processes that support more effective selling.
Strengthen pipeline generation and market presence. You will align sales, marketing, and partner development efforts to create a consistent flow of qualified opportunities. You will develop targeted demand generation strategies, strengthen channel relationships, and leverage CYBERWELL’s Microsoft partnership and technical expertise to expand market reach and support business development.
Collaborate across the business. You will partner closely with the CEO, executive leadership team, product leaders, and technical specialists to align commercial priorities with customer needs, delivery capabilities, and financial objectives. You will bring market intelligence and customer feedback into strategic discussions, helping shape product and service offerings and identify new opportunities for growth.
Own commercial performance. You will oversee sales and marketing budgets, resource planning, revenue forecasts, and performance against targets. You will use pipeline insights, sales metrics, and financial results to evaluate progress, make informed decisions, and adjust strategies to improve conversion, profitability, and long-term performance.

You bring

The sales leadership experience. You have successfully led and developed B2B technology sales teams, building or transforming sales organizations to achieve measurable revenue growth. You have experience recruiting, coaching, managing performance, and establishing the structure and accountability needed to help teams succeed. You are equally comfortable setting commercial strategy and working directly with salespeople and customers to advance opportunities.
The industry knowledge. You have a strong understanding of cybersecurity solutions and services, enterprise technology sales, and complex customer buying processes. You can connect technical capabilities to business challenges, risk management, and customer outcomes. Experience in cybersecurity is strongly preferred, although we will consider leaders from broader enterprise technology or highly regulated industries with relevant security exposure.
The commercial track record. You have demonstrated success developing go-to-market strategies, generating pipeline, winning new customers, and closing complex, high-value deals. You understand recurring revenue models, strategic account development, and how to navigate multiple stakeholders and lengthy sales cycles. You can point to measurable results and explain how your decisions contributed to growth.
The operational discipline. You have experience establishing repeatable sales processes, managing forecasts and budgets, and using performance data to guide decisions. You are highly proficient in Salesforce and know how to make it the single source of truth for pipeline management, forecasting, and commercial reviews. You can identify inefficiencies, simplify processes, and create the visibility and accountability needed to improve sales productivity.
The executive presence. You have experience engaging senior decision-makers, building strategic customer and partner relationships, and contributing to business decisions at the leadership level. You communicate with clarity and confidence, bring informed recommendations forward, and work collaboratively across sales, marketing, product, finance, and delivery teams.
The leadership approach. You lead by example, combining commercial ambition with integrity, empathy, and a commitment to developing others. You are comfortable making decisions, challenging assumptions, and navigating change while building trust and alignment across teams. You bring the energy, resilience, and hands-on approach needed to build momentum, strengthen performance, and deliver results.

Compensation

The base salary range for this position is $160,000 - $190,000, with a 50/50 base salary and commission structure, offering on-target earnings (OTE) of $320,000 - $380,000. The salary will be determined based on several factors, including the candidate’s experience, qualifications, skills, and the needs of the organization. At CYBERWELL , 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.

What you can expect from our interview process:

A virtual interview with a Talent Advisor to discuss your interest in joining the company and in the role. 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 interview with Michelle Lotoski to discuss your sales leadership experience, approach to building high-performing teams, and ability to drive commercial growth.
An interview with one or two Product Leaders to explore your experience partnering with technical teams, navigating complex enterprise sales, and aligning commercial strategy with customer needs.
A final interview with Peter Robertson and a Business Leader to discuss your leadership approach, strategic vision, and alignment with CYBERWELL's growth objectives.

Apply now.

Interested in applying but worried you don't have it all? At CYBERWELL , we know not everyone gains their experience following a traditional path. If you share our values, want to make a difference in cybersecurity solutions, and meet 70% of the qualifications, we encourage you to apply.

CYBERWELL 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.