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Regional Sales Director - Large Enterprise - Customer Base

Lead a high-performing sales team to secure large enterprise cloud solution contracts
Chicago
Senior
6 days ago
Illinois Staffing

Illinois Staffing

An official government entity providing employment resources and services to the residents of Illinois.

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Regional Sales Director

Your work days are brighter here. We’re obsessed with making hard work pay off, for our people, our customers, and the world around us. 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. The minute you join, you’ll feel it. Not just in the products we build, but in how we show up for each other. Our culture is rooted in integrity, empathy, and shared enthusiasm. We’re in this together, tackling big challenges with bold ideas and genuine care. We look for curious minds and courageous collaborators who bring sun-drenched optimism and drive. Whether you’re building smarter solutions, supporting customers, or creating a space where everyone belongs, you’ll do meaningful work with Workmates who’ve got your back. In return, we’ll give you the trust to take risks, the tools to grow, the skills to develop and the support of a company invested in you for the long haul. So, if you want to inspire a brighter work day for everyone, including yourself, you’ve found a match in Workday, and we hope to be a match for you too.

About the Team: Workmates pride themselves on winning while having fun! That means supporting each other while driving accountability for amazing results and performance. This team is no different. Everything we do inspires a brighter work day for all. The Enterprise Management Sales team at Workday helps the company to continue to grow by balancing integrity and innovation, ensuring Workmates have the environment to bring their best self, and get better by pushing and developing themselves and the Workmates around them.

About the Role

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 lead a team of passionate, enthusiastic and motivated people who want to be part of one of the most innovative and disruptive cloud companies on the planet. In this role, you will:

  • Be a key leader focused on driving new business for Workday
  • Lead a team focused on driving complex sales cycles through orchestrating internal teams of pre-sales, value management, bid management, inside sales, marketing and sales support
  • Use your experience to lead, coach and mentor a field sales team for your assigned territory
  • Employ effective selling strategies to successfully position Workday as a viable cloud partner of choice to alternative to legacy ERP solutions

About You

Basic Qualifications:

  • 2+ years of field sales management experience as 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 in 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

Other Qualifications:

  • Understanding of the strategic competitive landscape by staying up to date with trends and customer needs so you can effectively position Workday solutions within accounts
  • Proven experience of pulling together different business units to maximize on sales
  • Experience maintaining accurate forecasting data and business modeling for senior leadership
  • Self-starter attitude with the ability to work in a dynamic environment

Workday Pay Transparency Statement: The annualized base salary ranges for the primary location and any additional locations are listed below. Workday pay ranges vary based on work location. As a part of the total compensation package, this role may be eligible for the Workday Bonus Plan or a role-specific commission/bonus, as well as annual refresh stock grants. Recruiters can share more detail during the hiring process. Each candidate’s compensation offer will be based on multiple factors including, but not limited to, geography, experience, skills, job duties, and business need, among other things. For more information regarding Workday’s comprehensive benefits, please

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Regional Sales Director - Large Enterprise - Customer Base
Chicago
Sales Director
About Illinois Staffing
An official government entity providing employment resources and services to the residents of Illinois.