Regional Sales Director – Medium Enterprise

WillHire

Regional Sales Director leveraging extensive experience to lead a team at Workday. Driving new business and managing sales strategies for cloud solutions in a dynamic environment.

Posted 5/27/2026full-timeChicago • Illinois, Massachusetts, New York, Texas • 🇺🇸 United StatesLead💰 $174,000 - $261,000 per yearWebsite

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

field sales managementnew business acquisitioncloud solutionsSaaS solutionsERP solutionscomplex sales cyclesrevenue attainmentquota attainment

Soft Skills

leadershipcoachingmentoringrelationship cultivationteam collaborationeffective selling strategies

Industry Keywords

Workdaysales cyclespartnersalliancesteam selling environment

Tech Stack

Tools & technologies

CloudERP

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

2+ years of field sales management experience as a SaaS company, ideally focused on new business acquisition
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

Benefits

Comp & perks

Workday Bonus Plan
Annual refresh stock grants
Flexible work arrangements