Regional Sales Manager

Cornerstone OnDemand, Inc.
Chicago, IL

Enterprise Growth Market Position Overview

We are seeking a high-performing Regional Sales Manager to drive new business acquisition and strategic account expansion within a large, high-potential territory. This role is focused primarily on net-new prospecting (80%) into organizations with 5,000+ employees , with 20% dedicated to cross-sell and upsell opportunities within existing customers.

The ideal candidate is an experienced enterprise seller who excels in complex, multi-threaded sales cycles and is comfortable building relationships across C-suite and senior executive stakeholders.

In this role you will...

  • Own and execute a territory strategy for large enterprise organizations (5,000+ employees).

  • Prospect, qualify, and drive net-new sales opportunities across the full sales cycle from initial engagement to negotiation and close.

  • Lead multi-threaded pursuits, engaging stakeholders across HR, Talent, L&D, IT, Finance, and executive leadership.

  • Execute account planning and expansion strategies within existing customers to drive cross-sell and upsell opportunities.

  • Deliver compelling product presentations and business cases that articulate Cornerstone's differentiated value.

  • Collaborate closely with Solution Consultants, Customer Success, Marketing, and Product teams to support deal progression.

  • Maintain accurate pipeline forecasting and territory management through CRM.

  • Represent Cornerstone as a trusted advisor and subject matter expert in HCM/Talent technology.

You've got what it takes if you've got...

  • 5+ years of enterprise sales experience targeting large, complex organizations.

  • Proven track record of consistent performance and quota achievement in SaaS, HR tech, HCM, or related enterprise technology.

  • Demonstrated ability to lead multi-threaded , long sales cycles and engage C-level and senior executive stakeholders .

  • Strong business acumen with the ability to connect solutions to strategic business outcomes.

  • Excellent communication, presentation, and negotiation skills.

  • Ability to manage a large, high-volume territory with strong prioritization and pipeline discipline.

  • High degree of self-motivation, accountability, and ownership.

Preferred Qualifications

  • Experience selling HCM, Talent, Learning, or Workforce

  • Understanding of enterprise HR processes and digital transformation initiatives.

  • Background working with global enterprises and matrixed organizations.

Equal Employment Opportunity has been, and will continue to be, a fundamental commitment at Cornerstone OnDemand. All qualified applicants are given consideration regardless of race, color, gender, age, sexual orientation, national origin, marital status, citizenship status, disability, veteran status, or any other protected class as provided in applicable Federal, State, or Local fair employment laws. If you have a disability or special need that requires accommodation, please contact us at [email protected]

Posted 2026-02-06

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