Director, Enterprise Sales

Rippling•Chicago, IL

About The Position

As Director of Enterprise Sales, you will lead and develop a team of Sales Managers and Account Executives at a fast-paced, high-growth company. You will own recruiting, onboarding, ongoing training and development, and sales execution, directly influencing the growth of the Enterprise business. The role reports to the VP of Enterprise Sales. The Director provides inspirational sales leadership, grows top-line revenue, and drives new business by implementing scalable, repeatable, structured systems and processes. The role partners with customer executives and collaborates across the organization to align and execute regional Enterprise segment strategy, build consistent customer acquisition approaches, and exceed quarterly targets. Responsibilities also include sales forecasting, funnel metrics, and strategic and operational planning. Rippling values in-office work to foster collaboration and culture. Under the stated policy, employees who live within 40 miles of a Rippling office are expected to work in the office at least three days a week. Compensation includes competitive on-target earnings (base salary plus sales commission), benefits, and equity. For US-based employees, the stated on-target earnings range uses a 50/50 base and variable pay split; commission is not guaranteed. Final offers may vary based on professional background, experience, and location.

Requirements

BA/BS degree.
10+ years in software and/or applications sales.
Experience as a second-line leader.
Consistent overachievement of quota and revenue goals.
Experience selling deals up to $1 million in ARR.
High energy, autonomy, and an owner mindset.
Strong communication skills and executive presence when working with major clients.
Ability to collaborate across teams, navigate organizational challenges, and develop solutions that support continued growth.
A solid track record of recruiting, developing, and retaining a high-performing enterprise sales organization.

Nice To Haves

Experience selling HCM software to HR leadership and the CFO.
Experience selling HCM software and/or related products.

Responsibilities

Lead and develop Sales Managers and Account Executives.
Own recruiting, onboarding, training, and development for the sales team.
Lead sales execution and drive growth in the Enterprise business.
Grow top-line revenue and drive new business by implementing scalable, repeatable, structured systems and processes.
Partner with customer executives and navigate the needs of a fast-growing industry disruptor.
Align and execute the Enterprise segment strategy at a regional level to support consistent customer acquisition, growth, and quarterly target achievement.
Collaborate with functions and leaders across the organization to establish strong partnerships and continued success.
Provide detailed and accurate sales forecasts.
Manage the overall sales process and establish appropriate sales funnel management metrics.
Plan and manage at strategic and operational levels.
Recruit, develop, and retain a high-performing enterprise sales organization.