AI Enablement Lead

AI Enablement & Workforce Transformation Lead About Keystone AI Keystone AI is building the next generation of investment management technology. Founded by Tech visionary Dave Duffield, Keystone AI delivers a modern, cloud-native platform designed to transform how investment firms operate. As AI reshapes the future of work, Keystone AI is investing deeply in enabling every employee — across technical, operational, and business functions — to adopt and leverage AI skillfully. We believe AI transformation is not simply about deploying tools; it’s about fundamentally evolving how organizations learn, operate, and make decisions. To help lead that transformation, we’re building a new AI Enablement function focused on enterprise-wide learning, workforce transformation, and organizational adoption. The Opportunity We’re looking for an AI Enablement & Workforce Transformation Lead to design and build Keystone AI’s enterprise AI learning and adoption program from the ground up. This role is part strategist, part program builder, part educator, and part organizational change leader. You’ll partner with leaders across the business to define how AI will reshape their functions while simultaneously building scalable learning systems that help employees adopt AI tools confidently and proficiently. You’ll create differentiated learning experiences for technical teams, non-technical employees, operational functions, and executive leadership. You’ll also serve as a strategic advisor to functional leaders navigating how AI will transform their organizations over time. This role is ideal for someone who thrives in ambiguity, enjoys building from zero-to-one, and can bridge deep technical AI insight with applicable business transformation. What You’ll Do Design and build Keystone AI’s enterprise AI learning and enablement strategy Develop scalable AI learning programs across multiple employee audiences and skill levels Create learning tracks for technical, operational, business, G&A, and executive teams Facilitate workshops, training sessions, and executive enablement programs Partner with functional leaders to define how AI will reshape their organizations and workflows Build frameworks and accountability systems that drive measurable AI adoption Translate emerging AI capabilities into accessible, actionable learning content Collaborate closely with IT, security engineering, and AI systems teams to stay aligned on tooling and roadmap evolution Develop scalable operating models for AI upskilling and workforce transformation Help shape the long-term future of AI adoption and organizational capability at Keystone AI What You’ll Need Must Haves Experience leading AI enablement, AI adoption, or workforce transformation initiatives Learning & Development (L&D) program design and delivery experience Robust program management and organizational leadership capabilities Experience operating proficiently in highly ambiguous environments Sophisticated hands-on knowledge with modern AI tools and workflows Ability to simplify complex technical concepts for non-technical audiences Deep communication and executive presence Nice to Haves Engineering background or strong technical proximity to engineering organizations Experience building technical learning content Experience leading enterprise-wide organizational change initiatives Multi-functional career experience across business, operations, technology, or strategy Executive facilitation or coaching experience Experience designing scalable learning systems within fast-moving technology environments What Success Looks Like In your first several months, you’ll establish the foundation of Keystone AI’s enterprise AI enablement strategy and launch structured learning programs across multiple organizational audiences. Over time, success in this role means: Employees across the company measurably improve AI fluency and useful adoption Functional leaders actively advance AI transformation initiatives within their teams Keystone AI develops scalable systems for ongoing workforce upskilling AI learning evolves from ad hoc experimentation into an integrated organizational capability Compensation and Benefits The typical starting salary range for new hires in this role is $170,000 - $190,000. Final compensation amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amount listed above. As an employee at Keystone AI, you’ll have many opportunities for advancement in your career and can make a true impact on the product. In addition to the base salary, Keystone AI employees can participate in our Company Stock Plan subject to the applicable Stock Option Agreement. We also offer rich benefits that reflect the kind of organization we want to be: one in which our employees feel valued and are inspired to bring their best selves to work. These include unlimited vacation, educational and wellness reimbursements, and $0 cost employee insurance plans. Please check out our Careers page for a more comprehensive overview of our perks and benefits.