Head of Enterprise AI - United States

cyberu

3d•$230,800 - $369,300•Remote

About The Position

We're looking for a Head of Enterprise AI - United States This role is Remote, United States Head of Enterprise AI (3 month Fixed-Term position) Enterprise AI Discovery & Strategy • Engage directly with large enterprise customers to understand their AI transformation agendas, including productivity, skills, operating model change, workforce readiness, and business outcomes. • Identify common enterprise patterns, constraints, and opportunities that should shape product direction and go-to-market strategy. • Act as a trusted thought partner to customer executives navigating early-stage and scaled AI adoption. Connecting Strategy to Product & Value • Translate enterprise needs into clear use cases, value hypotheses, and success criteria for Cornerstone’s new AI product line. • Partner closely with product, engineering, and design teams to ensure enterprise realities are reflected in product decisions. • Help define what “good” looks like for enterprise AI adoption beyond pilots, demos, or surface-level automation. Customer Value & Delivery • Lead early customer engagements, pilots, and design partnerships to prove value and refine the offering. • Ensure customers see tangible outcomes, not just AI features—e.g., better decisions, faster readiness, reduced friction, or measurable productivity gains. • Work with services, partners, and internal teams to ensure delivery models scale without turning the product into bespoke consulting. Commercial Enablement • Support strategic sales motions by articulating the enterprise narrative, value proposition, and differentiation of this AI product line. • Help qualify opportunities, shape executive conversations, and accelerate complex enterprise deals. • Contribute to executive-level storytelling, customer references, and market credibility. Market & Ecosystem Insight • Track how leading enterprises are approaching AI across HR, operations, and the broader business. • Bring insights back into Cornerstone to inform positioning, partnerships, and long-term strategy. • Represent Cornerstone with credibility in executive briefings, industry forums, and strategic customer discussions. What Success Looks Like • Enterprise customers clearly understand how Cornerstone’s AI capabilities connect to their highest-priority transformation outcomes. • Early adopters achieve demonstrable value that can be repeated and scaled. • Product and go-to-market teams gain clarity and confidence from real enterprise signal—not assumptions. • Cornerstone establishes credibility as a serious, outcome-driven enterprise AI partner, not just another AI feature vendor. Why Cornerstone Cornerstone operates at global scale, serving some of the world’s largest and most regulated organizations. We have deep customer trust, strong traction, and a proven platform foundation through Galaxy. This role is an opportunity to shape what comes next: an enterprise-grade AI product line built for real outcomes, not hype. If you are motivated by defining new categories, working directly with senior enterprise leaders, and turning AI promise into operational reality, this role offers rare scope and impact. Our Culture: Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today. Who We Are: Cornerstone powers the potential of organizations and their people to thrive in a changing world. Cornerstone Galaxy, the complete AI-powered workforce agility platform, meets organizations where they are. With Galaxy, organizations can identify skills gaps and development opportunities, retain and engage top talent, and provide multimodal learning experiences to meet the diverse needs of the modern workforce. More than 7,000 organizations and 100 million+ users in 180+ countries and in nearly 50 languages use Cornerstone Galaxy to build high-performing, future-ready organizations and people today. Total Rewards: At Cornerstone, we are dedicated to inspiring excellence and pushing boundaries in everything we do. Our compensation strategy is based on three fundamental principles: equitable pay, market-driven research, and skill-based appraisals. As part of our mission to share success and empower individuals to thrive in an ever-changing world, the listed salary range is just one element of Cornerstone’s comprehensive compensation package. This compensation package may also include annual bonuses, short- and program-specific awards depending on the role, and a comprehensive benefit offering. The disclosed salary range reflects the geographic differential based on the location of the position if applicable. The starting salary for the successful applicant will depend on several job-related factors, including education, training, experience, certifications, location, business needs, and market demands. This range is based on a full-time position and may be adjusted in the future. Join us in shaping the future of work — tomorrow, together. Experience flexibility and empowerment in your career at Cornerstone. The BASE salary range for this position is: 230800 - 369300 USD.

Requirements

Senior experience working with large, complex enterprises on technology-driven transformation initiatives.
Proven ability to operate across strategy, product, and customer delivery—not confined to a single function.
Deep understanding of how AI is being adopted inside enterprises today, including organizational, data, governance, and change-management challenges.
Comfort engaging C-level executives with confidence and substance.
Experience in enterprise software, platforms, or large-scale transformation programs (vendor, operator, or hybrid background).
Strong judgment, clarity of thought, and ability to connect dots across people, process, and technology.

Responsibilities

Engage directly with large enterprise customers to understand their AI transformation agendas, including productivity, skills, operating model change, workforce readiness, and business outcomes.
Identify common enterprise patterns, constraints, and opportunities that should shape product direction and go-to-market strategy.
Act as a trusted thought partner to customer executives navigating early-stage and scaled AI adoption.
Translate enterprise needs into clear use cases, value hypotheses, and success criteria for Cornerstone’s new AI product line.
Partner closely with product, engineering, and design teams to ensure enterprise realities are reflected in product decisions.
Help define what “good” looks like for enterprise AI adoption beyond pilots, demos, or surface-level automation.
Lead early customer engagements, pilots, and design partnerships to prove value and refine the offering.
Ensure customers see tangible outcomes, not just AI features—e.g., better decisions, faster readiness, reduced friction, or measurable productivity gains.
Work with services, partners, and internal teams to ensure delivery models scale without turning the product into bespoke consulting.
Support strategic sales motions by articulating the enterprise narrative, value proposition, and differentiation of this AI product line.
Help qualify opportunities, shape executive conversations, and accelerate complex enterprise deals.
Contribute to executive-level storytelling, customer references, and market credibility.
Track how leading enterprises are approaching AI across HR, operations, and the broader business.
Bring insights back into Cornerstone to inform positioning, partnerships, and long-term strategy.
Represent Cornerstone with credibility in executive briefings, industry forums, and strategic customer discussions.