Regional Sales Director, Large Enterprise Customer Base

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.

We are looking for an exceptional leader with a stellar sales record that will capitalize on strategic accounts, be a self-starter and love working in a dynamic environment with an amazing team of people.

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

M5:

Basic Qualifications

• ~2+ years of field sales management experience as a SaS 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

M4:

Basic Qualifications

• ~12+ years of field sales experience at a SasS company, ideally focused on new business acquisition

• 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 is proud to be an equal opportunity workplace.

Further, pursuant to applicable local ordinances, Workday will consider for employment qualified applicants with arrest and conviction records.

You may view the Workday's Pay Transparency Policy, and Equal Employment Opportunity is the Law notice, by clicking on their corresponding links.

Workday is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans during our application process. If you need assistance or an accommodation due to a disability, contact us at View email address on aiapply.co.

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 click here .

Primary Location: USA.IL.ChicagoPrimary Location Base Pay Range: $174,000 USD - $261,000 USDAdditional US Location(s) Base Pay Range: $174,000 USD - $261,000 USD

Additional Considerations:

If performed in Colorado, the pay range for this job is $174,000 USD - $261,000 USD based on min and max pay range for that role if performed in CO.

The application deadline for this role is the same as the posting end date stated as below:

10/30/2026

Our Approach to Flexible Work

With Flex Work, we’re combining the best of both worlds: in-person time and remote. Our approach enables our teams to deepen connections, maintain a strong community, and do their best work. We know that flexibility can take shape in many ways, so rather than a number of required days in-office each week, we simply spend at least half (50%) of our time each quarter in the office or in the field with our customers, prospects, and partners (depending on role). This means you'll have the freedom to create a flexible schedule that caters to your business, team, and personal needs, while being intentional to make the most of time spent together. Those in our remote "home office" roles also have the opportunity to come together in our offices for important moments that matter.

Pursuant to applicable Fair Chance law, Workday will consider for employment qualified applicants with arrest and conviction records.

Workday is an Equal Opportunity Employer including individuals with disabilities and protected veterans.

Workday is committed to providing reasonable accommodations for qualified individuals during our application process, in order to perform one or more essential functions of their job, as well as regarding the use of AI tools for employment decision-making to any degree. Please see below for more details including how to request an accommodation as a qualified veteran, due to a disability or for religious reasons, or as otherwise provided under applicable law.

Workday prohibits taking adverse action against any candidate or employee for reporting a possible violation of this policy, requesting one or more work accommodations, exercising a privacy right, or cooperating in an investigation in accordance with applicable law. Any employee who retaliates against a candidate or employee for doing so may be subject to disciplinary action, up to and including termination of employment, to the fullest extent allowable under applicable law.

If you require a reasonable accommodation, you may email View email address on aiapply.co , as far in advance as possible.

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