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Package Description:
Work 1:1 with an expert AI strategist for a comprehensive engagement covering the full spectrum of AI strategy and transformation, from building personal AI fluency through driving organizational change. Possible uses of coaching sessions, but not limited to: - Building AI fluency and executive AI leadership skills - Developing organizational AI strategy and roadmap - AI readiness assessment and implementation planning - Team upskilling and change management - AI governance, policy, and responsible AI frameworks - Fractional AI consulting and business development - AI-driven growth: marketing, sales, and product innovation - Relevant live trainings and workshops tailored to your team's needs
What you'll get from this package
A comprehensive AI strategy and transformation plan tailored to your organization
Hands-on skills in AI fluency, leadership, and change management
A governance and responsible AI framework built for your context
Practical tools for using AI to drive growth across marketing, sales, and product
Live trainings and workshops tailored to your team's specific needs
Additional details
Coaching delivered via live sessions and .
Services included:
AI Automation
AI Readiness Assessment
AI Strategy
AI Roadmap Development
AI Tools & Integration
Team AI Upskilling
AI Policy & Governance Design
AI-Driven Marketing
AI-Driven Sales
AI Product Innovation
Fractional AI Strategist
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
More packages from Cheryl
Custom hourly · $195/hr
Get help with AI Readiness Assessment, AI Strategy, and .
Cheryl also coaches for Leadership Coaching, Career Coaching, and Business Operations & Strategy. View all.
Offered by Cheryl T.
Joined February 2026
5.0
Former VP coaching executives who have to lead AI and need someone who has
I previously served as VP of AI Transformation at Cielo Talent, where I identified 128 AI use cases across 18 business functions, deployed five working AI agents that delivered measurable business value, and built a 2,196-member transformation community generating over 10,000 post views in a single quarter. I was promoted to that role within three months because I could see what the organization needed before anyone had named it. That is the same instinct I bring to this coaching. What I know from building AI strategy inside a real enterprise is that the leaders who navigate it well are not the ones who learned the most tools. They are the ones who developed the judgment to know when AI helps, when it does not, and how to bring other people along. That is the work this coaching is built around.
Starting at $1,755
10h+ of coaching