Senior Regional Sales Manager
WFA Digital Insight
The demand for AI-driven sales professionals grew 25% in 2025, with companies like Cornerstone onDemand leading the charge. As a Senior Regional Sales Manager, you'll be at the forefront of this trend, leveraging Excel skills to drive pipeline growth. With the rise of remote work, companies are looking for skilled professionals who can navigate complex sales environments and build strong relationships with clients. Before applying, candidates should be aware of the evolving landscape of AI sales and the importance of simplifying technical concepts for both technical and non-technical audiences.
Job Description
About the Role
As a Senior Regional Sales Manager at Cornerstone onDemand, you will be responsible for driving commercial success for the company's emerging Workforce AI platform. This role is ideal for someone who thrives in visionary, early-stage product environments and excels at helping customers understand the transformative power of AI for skills, productivity, talent intelligence, and workforce optimization. You will be working closely with Account Executives and product teams to deliver high-impact discovery sessions and build strong relationships within key customer accounts.The sales motion for Cornerstone's Workforce AI solutions requires a deep understanding of the market and the ability to simplify technical concepts for both technical and non-technical audiences. As a Senior Regional Sales Manager, you will be expected to lead the sales effort and drive pipeline growth, while also partnering with AEs and product teams to deliver high-impact discovery sessions.
The role is part of a fast-evolving product space, and the ideal candidate will be curious, adaptable, and comfortable working in a dynamic environment. With the rise of remote work, this role offers the opportunity to work with a global team and build strong relationships with clients across different regions.
What You Will Do
- Lead the sales motion for Cornerstone's Workforce AI solutions
- Drive pipeline growth and partner with AEs and product teams
- Deliver high-impact discovery sessions and build strong relationships within key customer accounts
- Simplify technical concepts and communicate AI value to both technical and non-technical audiences
- Work in an overlay, matrixed, or highly collaborative sales model
- Hit or exceed sales targets in consultative, enterprise, or mid-market sales environments
- Collaborate with cross-functional teams to develop and execute sales strategies
- Provide feedback and insights to product teams to inform product development
- Develop and maintain a deep understanding of the market and industry trends
- Identify and pursue new business opportunities and expand existing relationships
What We Are Looking For
- 2+ years of direct experience selling AI-driven solutions
- Background from niche or specialized AI vendors
- Proven success selling complex, intangible, or emerging technologies
- Experience in an overlay, matrixed, or highly collaborative sales model
- Strong ability to simplify technical concepts and communicate AI value to both technical and non-technical audiences
- Track record of hitting or exceeding sales targets in consultative, enterprise, or mid-market sales environments
- Excellent communication skills and executive presence
- Ability to work in a fast-evolving product space and adapt to changing market conditions
- Strong analytical skills and proficiency in Excel
Nice to Have
- Experience working with Cornerstone's Workforce AI platform or similar technology
- Knowledge of the HR technology market and industry trends
- Familiarity with sales enablement tools and technologies
- Certification in sales or a related field
Benefits and Perks
- Competitive salary and bonus structure
- Opportunity to work with a global team and build strong relationships with clients
- Comprehensive benefits package, including health, dental, and vision insurance
- Generous PTO and holiday policy
- Remote work stipend and flexible working hours
- Professional development opportunities, including training and education programs
- Access to the latest sales enablement tools and technologies
- Recognition and reward programs for outstanding performance
How to Stand Out
- Develop a strong understanding of the AI sales landscape and the latest industry trends to stand out in your application.
- Be prepared to provide specific examples of your experience selling complex, intangible, or emerging technologies.
- Highlight your ability to simplify technical concepts and communicate AI value to both technical and non-technical audiences.
- Showcase your skills in Excel and your ability to drive pipeline growth and hit sales targets.
- Research Cornerstone onDemand's Workforce AI platform and be prepared to ask informed questions during the interview process.
- Be prepared to discuss your experience working in an overlay, matrixed, or highly collaborative sales model and how you can apply this experience to the role.
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