Head of Sales, North America

This is a strategic leadership opportunity for an accomplished enterprise sales executive ready to drive regional growth and build a high-performing sales organization in North America.

About the role

You will lead the North American sales strategy, oversee revenue performance, and play a pivotal role in expanding enterprise customer relationships. Working in a fast-paced, remote-first environment, you will collaborate closely with executive leadership and cross-functional teams to shape go-to-market initiatives and accelerate business growth. This role combines hands-on deal leadership with people development, requiring a leader who thrives in scaling teams, improving sales execution, and winning complex enterprise opportunities.

Responsibilities

• Own and execute the North American sales strategy, achieving regional revenue targets through new business acquisition and strategic account expansion.
• Lead, mentor, and develop a high-performing enterprise sales team, fostering accountability, collaboration, and continuous improvement.
• Establish disciplined sales processes across pipeline management, forecasting, opportunity reviews, and performance tracking.
• Personally support strategic enterprise opportunities by contributing to executive engagement, deal strategy, negotiations, and contract execution.
• Develop regional and industry-focused growth strategies to strengthen market presence and expand customer relationships.
• Build trusted partnerships with executive-level customer stakeholders and position solutions as key enablers of business transformation.
• Collaborate closely with Growth, Solutions, Partnerships, Customer Success, and Product teams to improve pipeline quality, increase win rates, and ensure successful customer outcomes.
• Deliver accurate sales forecasts and performance insights to executive leadership using data-driven decision making.
• Recruit, onboard, and develop top sales talent to support ongoing business expansion.
• Share customer, market, and competitive insights to help refine sales strategies, product direction, and go-to-market initiatives.

Requirements

• 10+ years of enterprise software sales experience, including significant leadership experience managing enterprise sales organizations.
• Demonstrated success achieving multi-million-dollar revenue targets within enterprise SaaS environments.
• Proven ability to build, coach, and scale high-performing sales teams focused on consistent execution and measurable results.
• Extensive experience leading complex, multi-stakeholder enterprise sales opportunities from strategy through successful close.
• Strong executive presence with the ability to build credibility and long-term relationships with C-level customers and internal leadership.
• Deep understanding of enterprise sales methodologies, business case development, procurement processes, contract negotiations, and strategic account management.
• Strong commercial acumen with excellent analytical and decision-making skills.
• Experience within Field Service Management, Workforce Management, Asset Management, enterprise operations, or related industries is highly desirable.
• Entrepreneurial mindset with the ability to thrive in high-growth, fast-changing environments.
• Player-coach leadership style with a passion for developing people while remaining actively engaged in strategic sales opportunities.
• Outstanding communication, leadership, and cross-functional collaboration skills.

Benefits

• Remote-first work environment with flexibility to work anywhere in the United States.
• Opportunity to lead a high-impact regional sales organization with significant executive visibility.
• Competitive compensation package with performance-based incentives.
• Career growth opportunities within a rapidly scaling global technology company.
• Collaborative international environment with cross-functional leadership exposure.
• Opportunity to influence company strategy, sales processes, and organizational growth.
• Work with innovative technology focused on transforming frontline workforce productivity.