Medium Enterprise Regional Sales Director - Local Government

Your work days are brighter here. We’re obsessed with making hard work pay off for our people, customers, and the world. As a Fortune 500 company and a leading AI platform for managing people, money, and agents, we’re shaping the future of work so teams can reach their potential and focus on what matters most. You’ll feel it in the products we build, in our culture rooted in integrity, empathy, and shared enthusiasm, and in the support of a company invested in you for the long haul.

Workmates pride themselves on winning while having fun—supporting each other while driving accountability for amazing results. The Enterprise Management Sales team helps the company grow by balancing integrity and innovation and enabling Workmates to bring their best selves to work.

As a Regional Sales Director, you will use your extensive sales and leadership experience to lead, coach, and mentor a team of Senior Account Executives selling Workday’s Solutions. You will drive new business, orchestrate complex sales cycles, and position Workday as the cloud partner of choice to alternative legacy ERP solutions.

• Lead a team focused on driving new business for Workday.
• Drive complex sales cycles by coordinating internal teams of pre‑sales, value management, bid management, inside sales, marketing, and sales support.
• Coach and mentor a field sales team for your assigned territory.
• Employ effective selling strategies to position Workday as a viable cloud partner.

• 2+ years of field sales management experience at a SaaS company, ideally focused on new business acquisition, with additional 10+ years as a field sales representative.
• Experience selling cloud / SaaS / ERP solutions.
• Experience cultivating relationships with partners and alliances.
• Experience managing complex sales cycles from start to finish with a track record of successful revenue/quota attainment.
• Experience as a leader in a team selling environment.

• 12+ years of field sales experience at a SaaS company, ideally focused on new business acquisition.
• Experience selling cloud / SaaS / ERP solutions.
• Experience cultivating relationships with partners and alliances.
• Experience managing complex sales cycles from start to finish with a track record of successful revenue/quota attainment.
• Experience as a leader in a team selling environment.

• Understanding of the strategic competitive landscape by staying up to date with trends and customer needs.
• Proven experience pulling together different business units to maximize sales.
• Experience maintaining accurate forecasting data and business modeling for senior leadership.
• Self‑starter attitude with the ability to work in a dynamic environment.

Annualized base salary ranges for the primary location (USA IL Chicago) are $174,000 USD – $261,000 USD. The role may be eligible for the Workday Bonus Plan, a role‑specific commission, and annual refresh stock grants. Compensation offers depend on geography, experience, skills, job duties, and business need.

We spend at least 50% of our time each quarter in the office or in the field, allowing you to create a flexible schedule that caters to your business, team, and personal needs while maintaining strong community connections.

Workday is an Equal Opportunity Employer. We consider applicants with arrest and conviction records in accordance with applicable Fair Chance law. Workday provides an accessible and inclusive hiring experience; please email  if you require assistance.