AI Enablement & Workforce Transformation Lead
About Ridgeline
Ridgeline is building the next generation of investment management technology. Founded by Tech visionary Dave Duffield, Ridgeline delivers a modern, cloud-native platform designed to transform how investment firms operate.
As AI reshapes the future of work, Ridgeline 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 Ridgeline’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 Ridgeline’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 Ridgeline
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 Ridgeline’s enterprise AI enablement strategy and launch structured learning programs across multiple organizational audiences.
Employees across the company measurably improve AI fluency and useful adoption
Functional leaders actively advance AI transformation initiatives within their teams
Ridgeline 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 Ridgeline, 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, Ridgeline 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.