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Director, Enterprise Sales

Rippling - Remote - Hybrid - posted 2026-10-20

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Rippling is a unified platform for HR, IT, and Finance that brings together workforce systems—payroll, expenses, benefits, computers, and third-party app integrations—into a single system. The company has raised $1.2B from top-tier investors and was named one of America's best startup employers by Forbes. As Director of Enterprise Sales, you will lead and develop a team of Sales Managers and Account Executives, driving growth for the Enterprise business segment. You report to the VP of Enterprise Sales and own recruiting, onboarding, training, development, and sales execution for your team. Key responsibilities include: - Lead inspirational sales leadership and management, growing top-line revenues and driving new business through scalable, repeatable systems and processes - Partner with customer executives and navigate a fast-growing, industry-disrupting market - Align and execute Enterprise segment strategy at a regional level to generate growth and exceed quarterly targets - Manage a growing sales organization of Sales Managers and Account Executives to win new business - Collaborate across functions and organizational leaders to establish strong partnerships - Provide detailed and accurate sales forecasting and manage the overall sales process - Set appropriate metrics for sales funnel management - Plan and manage at both strategic and operational levels Note: Rippling values in-office collaboration. For employees within 40 miles of a Rippling office, working in-office at least three days per week is considered an essential function of the role. REQUIREMENTS: - BA/BS Degree - 10+ years in software and/or applications sales - Experience as a 2nd line leader (managing managers) - Consistent overachievement of quota and revenue goals - Experience selling HCM software and related products preferred - Experience selling deals up to $1M in ARR - Experience selling HCM software to HR leadership and CFO preferred - High energy and owner mindset; ability to move fast with autonomy - Strong communication skills and executive presence with large clients - Ability to collaborate across teams and navigate organizational challenges - Solid track record of recruiting, developing, and retaining high-performing enterprise sales organizations

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