Senior Regional Sales Manager

Cornerstone Workforce AI Sales Executive

About the Role

Cornerstone is expanding our go to market team with a new Cornerstone Workforce AI Sales Executive, focused on driving commercial success for our 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.

As an overlay seller (maybe?), you will partner closely with account executives across segments, bringing deep expertise in AI solutions and guiding customers through complex, conceptual buying journeys. This is a high impact role that blends strategic storytelling, technical curiosity, and strong sales execution.

In this role you will…

• Lead the sales motion for Cornerstone’s Workforce AI solutions, serving as the primary subject-matter expert throughout the deal cycle.

• Drive pipeline growth by identifying AI use cases within customer environments and translating them into compelling value propositions.

• Partner with AEs, solution consultants, and product teams to support AI-focused opportunities across assigned territories.

• Deliver high-impact discovery sessions, product walkthroughs, and business-case presentations tailored to senior HR, IT, and business leaders.

• Build strong relationships within key customer accounts, elevating Cornerstone as a trusted advisor in Workforce AI transformation.

• Navigate conceptual, intangible, or future-state solution sales — helping customers understand what’s possible, not only what exists today.

• Maintain up-to-date understanding of emerging AI trends, niche AI vendors, and competitive landscapes.

• Contribute feedback to product and marketing teams based on customer needs and market signals to influence roadmap and positioning.

You’ve got what it takes if you have…

• 2+ years of direct experience selling AI-driven solutions, ideally in workforce, HR tech, talent intelligence, productivity AI, or adjacent B2B SaaS categories.

• Background from niche or specialized AI vendors, start-ups, or innovation-focused teams where selling a vision is essential.

• Proven success selling complex, intangible, or emerging technologies where buyer education and conceptual storytelling are required.

• Experience in an overlay, matrixed, or highly collaborative sales model strongly preferred.

• Strong ability to simplify technical concepts and communicate AI value to both technical and nontechnical audiences.

• Track record of hitting or exceeding sales targets in consultative, enterprise, or mid market sales environments.

• Curiosity, adaptability, and comfort working in a fast-evolving product space.

• Excellent communication skills and executive presence.

Extra Does of Awesome if you have…

• Understanding of LLMs, machine learning basics, or AI architectures applied to workforce or skills data.

• Prior experience selling into HR, Talent, or People Analytics functions.

• Exposure to skills intelligence, workforce planning solutions, or talent mobility platforms.

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 View email address on click.appcast.io