Why Join Us?

Check Point Software Technologies is seeking a seasoned, high-impact sales leader to serve as Head of Canada Sales. This is a senior leadership role responsible for the full commercial performance of Check Point's Canada business — spanning enterprise, public sector, mid-market, and partner channels. You will build and lead a world-class team, drive transformational growth, and serve as the primary advocate for Canada's customers, partners, and sellers within the Americas and global organization.

You bring deep expertise in selling complex, multi-vendor cybersecurity or infrastructure solutions across both Canadian public sector and commercial enterprise accounts. You understand how to win at scale — through GSIs, national VARs, and SIs — and how to grow a pipeline that reflects both near-term execution and long-range strategic opportunity.

Key Responsibilities

Sales Leadership & Execution

• Own revenue attainment and growth targets across Canada, including enterprise commercial, public sector, and partner-influenced business.

• Drive rigorous forecast discipline — weekly, monthly, and quarterly — with a high standard for accuracy, coverage, and pipeline quality.

• Develop and execute Canada's go-to-market strategy, aligning segment priorities (Federal, Provincial, Municipal, Healthcare, Financial Services, Enterprise) with capacity, coverage, and channel investments.

• Lead pursuit of major strategic accounts and complex, multi-vendor competitive opportunities from qualification through close.

• Champion account transition and coverage best practices to ensure continuity and customer confidence.

People Leadership & Talent Development

• Lead as a leader of leaders — recruiting, developing, and retaining high-performing regional and segment sales managers across Canada.

• Foster a culture of accountability, coaching, inclusivity, and continuous improvement.

• Drive employee engagement and retention through intentional culture-building, recognition, and career pathing.

• Own performance calibration, development planning, and succession readiness for your leadership team.

• Partner with Talent Acquisition and HR to hire ahead of growth and close representation gaps.

Channel & Partner Ecosystem

• Build and maintain executive-level relationships with Canada's leading GSIs, national VARs, SIs, and distributors.

• Develop joint go-to-market plans with strategic partners aligned to Check Point's platform and technology priorities.

• Drive partner enablement and engagement to maximize co-sell motions and influenced pipeline.

• Leverage the channel to extend market coverage, accelerate deals, and expand into net-new accounts.

Public Sector Expertise

• Lead Check Point's pursuit of Federal, Provincial, and Municipal government opportunities with deep familiarity of Canadian public sector procurement frameworks (PSPC, TBIPS, ProServices, provincial vehicles).

• Navigate complex, multi-stakeholder deals across defense, civilian agencies, healthcare, education, and Crown corporations.

• Build relationships with key government influencers, advisors, and ecosystem partners to position Check Point as a preferred, trusted supplier.

Cross-Functional & Corporate Leadership

• Represent Canada's interests and advocate for the right resources, priorities, and investments at the Americas and global level.

• Align the Canada business with Americas-wide programs, initiatives, and corporate directives without sacrificing local relevance or speed.

• Partner with Marketing, Sales Engineering, Customer Success, and Finance to ensure a unified go-to-market and customer experience.

• Provide regular business reviews and strategic updates to the President, Americas Sales and executive leadership.

How Success is Measured

This leader will be evaluated across four dimensions:

• Revenue Attainment — Quota performance across all segments, products, and lines of business.

• Pipeline Development — Qualified pipeline coverage ratio, pipeline creation velocity, and pipeline health by segment.

• Employee Engagement & Retention — Manager effectiveness scores, team retention rates, and internal mobility outcomes.

• Forecast Accuracy — Commit-to-close variance and quarter-over-quarter forecasting discipline.

Qualifications

• 10+ years of progressive B2B technology sales experience, with at least 5 years in a leader-of-leaders role managing regionally distributed teams.

• Demonstrated track record of quota attainment and business growth in Canada, with P&L or full commercial accountability.

• Deep familiarity with Canadian public sector procurement — including Federal and Provincial frameworks — and a proven ability to win large, competitive government contracts.

• Experience selling complex, multi-vendor solutions in cybersecurity, infrastructure, networking, or an adjacent technical domain.

• Established executive relationships with Canada's top GSIs, national VARs, and SIs, with a proven ability to build and scale channel-influenced pipeline.

• Experience operating within a global, matrixed organization while maintaining strong regional autonomy and advocacy.

Leadership Competencies

• Builder mentality — comfortable standing up teams, processes, and culture in a growth-stage regional business.

• Data-driven decision-making with high standards for forecast accuracy and pipeline hygiene.

• Strong executive presence and communication skills — credible with CISOs, CIOs, government executives, and board-level stakeholders.

• Talent magnet — known for recruiting, developing, and retaining A-players and building teams people want to stay on.

• High EQ with a bias toward direct, transparent, and motivating leadership communications.

• Collaborative by nature, competitive by instinct — able to advocate for Canada while contributing to the broader Americas team's success.

Preferred Background

• Background in cybersecurity, network infrastructure, cloud security, or adjacent SaaS/platform sales.

• Familiarity with security frameworks relevant to Canadian compliance and data sovereignty requirements (e.g., ITSG-33, Protected B/C environments).

• Prior experience at a publicly traded global technology company navigating complex organizational dynamics desired.

• Bilingual (English/French) a meaningful asset, particularly given the Quebec public sector landscape.

Additional Requirements

This role requires regular domestic travel across Canada to support key accounts, partner relationships, and team engagement, as well as periodic travel internationally including, but not limited to the United States and Israel for planning, leadership meetings, customer events, and corporate programs. Travel is expected at approximately 40-50% of working time. Maintaining a valid passport and appropriate visas is expected.