Director, Strategic Sales

This senior leadership role is responsible for driving strategic account growth across the Americas, with a strong focus on Retail and QSR loyalty.
You will own revenue performance while leading and expanding a team of Strategic Account Executives managing complex enterprise relationships.
The role requires a proven ability to navigate long, consultative sales cycles involving multiple stakeholders and senior decision-makers.
You will coach experienced sales professionals, strengthen pipeline generation, and establish repeatable processes for forecasting and deal management.
Working closely with Marketing, Customer Success, and Product, you will deepen strategic customer relationships and influence go-to-market priorities.
You will also introduce modern sales technologies and AI-driven approaches that help the team operate efficiently and scale its impact.
This is a remote U.S. role, with a preference for candidates near Chicago, Boston, or New York City, and occasional domestic and international travel of less than 50%.

• 10+ years of enterprise SaaS go-to-market experience, including at least 5 years of direct sales leadership and people management.
• Proven experience owning enterprise, strategic, or key account relationships rather than focusing solely on broader enterprise sales.
• Deep expertise in at least one major sales methodology, such as MEDDPICC, Sandler, Challenger, or Force Management, with working knowledge of additional methodologies.
• Demonstrated success navigating complex, multi-stakeholder sales processes and building trusted relationships with senior decision-makers.
• Proven ability to maintain sales velocity and momentum throughout long, consultative enterprise sales cycles.
• Strong coaching capabilities, particularly with experienced and high-performing sales professionals, with the ability to help tenured representatives reach a higher level of performance.
• Experience building scalable sales processes rather than relying primarily on individual effort or informal practices.
• Strong understanding and practical use of modern sales tools and AI to improve pipeline generation, forecasting, productivity, and deal execution.
• Strong commercial judgment, strategic thinking, communication, and relationship-building skills.
• Ability to work remotely while collaborating effectively across functions and time zones.
• Comfortable working Eastern or Central Time Zone hours.
• Willingness to travel domestically and internationally on an occasional basis, generally less than 50% of the time.