Head of Americas Strategic Initiatives and Field Execution

Check Point Software Technologies has been honored by Time Magazine as one of the World's Best Companies. We've also earned a spot on the Forbes list of the World's Best Places to Work for five consecutive years and recognized as one of the World's Top Female-Friendly Companies. If you're passionate about making the world a safer place and want to be part of an award-winning company culture, we invite you to join us.

Check Point Software Technologies is seeking a strategic operator to serve as Head of Americas Strategic Initiatives and Field Execution. This role combines chief of staff responsibilities with hands-on execution of critical sales transformation initiatives across the Americas region. You will be the President's strategic right hand, driving operational excellence, orchestrating major sales events, and ensuring flawless execution of go-to-market programs that enable our sales organization to exceed targets.

Field Execution & Sales Transformation (60%)

• Lead execution of sales transformation initiatives including organizational restructuring, process optimization, and methodology adoption across Americas sales teams
• Design and implement go-to-market programs, sales plays, and competitive displacement campaigns
• Drive adoption of sales processes and methodologies, working directly with field sales leadership to ensure consistent execution
• Own rollout and change management for major organizational initiatives, translating strategy into actionable field programs
• Partner with Sales Operations on pipeline management, forecast accuracy improvement, and sales productivity initiatives

Chief of Staff & Strategic Planning (25%)

• Serve as strategic advisor and operational right-hand to the President of Americas Sales
• Manage executive calendar, prioritize strategic initiatives, and ensure leadership bandwidth is focused on highest-impact activities
• Prepare executive briefings, board materials, and strategic presentations for C-suite and investor audiences
• Coordinate cross-functional initiatives across Sales Operations, HR, Business Analysis, and regional sales leadership
• Lead strategic planning cycles including annual planning, QBR preparation, and business performance analysis

Content Management & Event Orchestration (15%)

• Own end-to-end planning and execution of Americas Sales Kick-Off (SKO), including content development, speaker coordination, and logistics
• Host and produce quarterly business reviews (QBRs), translating data insights into compelling business narratives
• Create high-impact presentations for all-hands meetings, leadership offsites, and customer/partner events
• Manage content library and knowledge management systems for sales enablement materials
• Develop executive communications including keynote presentations, team announcements, and organizational change messaging

Key Partnerships

• Head of Americas Sales Operations: Joint ownership of forecast processes, territory planning, and sales productivity initiatives
• Americas HR Business Partner: Organizational design, talent strategy, and change management for restructuring
• Head of Business Analysis: Data insights, performance analytics, and QBR content development
• Regional Sales VPs: Program adoption, feedback loops, and field execution accountability

Success Metrics

• Americas sales team performance against revenue targets and key sales productivity metrics
• Strategic initiative completion rates and quality of execution
• Sales process adoption and methodology adherence across field teams
• QBR and SKO content quality, executive satisfaction, and sales team engagement scores
• Forecast accuracy improvement and pipeline health metrics

• 10+ years of experience in enterprise technology sales, sales operations, strategy, or management consulting
• Proven track record in cybersecurity or IT infrastructure sales environments
• Demonstrated success leading large-scale organizational change and sales transformation initiatives
• Exceptional executive presence and ability to create compelling presentations for C-suite audiences
• Strong analytical skills with ability to translate data into actionable insights and business narratives
• Experience planning and executing large-scale sales events (500+ attendees)
• Outstanding project management skills with ability to drive multiple complex initiatives simultaneously
• Willingness to travel 40-50% across Americas region

Preferred:

• Prior Chief of Staff or strategic advisor experience to sales executives
• Deep knowledge of cybersecurity market dynamics, competitive landscape, and buyer behaviors
• Experience with sales methodologies (MEDDPICC, Challenger, Command of the Message)
• Background in B2B SaaS or enterprise software sales
• MBA or equivalent advanced degree

What We Offer

• Opportunity to shape the strategic direction of a multi-billion dollar cybersecurity leader
• Direct partnership with executive leadership on company-defining initiatives
• High-visibility role with broad exposure across the organization
• Competitive compensation including base salary, performance bonus, and equity
• Comprehensive benefits package

Must be eligible to work in the United States without sponsorship from an employer now or in the future.