The CEO Shift
Why founder-dependence limits growth and what must change when an entrepreneur moves from doing everything to leading the business.
For founders, executives, and leadership teams
Keynotes, Panels, Workshops & Conversations
Give your audience more than inspiration. Give them a stronger next decision.
Jay Adewole delivers practical business conversations for entrepreneurs, executives, leadership teams, founders, and ambitious builders who need clearer thinking around strategy, systems, leadership, artificial intelligence, revenue, and scalable growth.
Business Strategy
Clear ideas grounded in execution
Audience Value
Practical frameworks and decisions
Flexible Formats
Live, virtual, panel, and workshop
Speaking philosophy
Make the conversation useful.
Every session should help the audience understand the issue, challenge an assumption, and leave with a practical next move.
Featured & Trusted
A trusted voice across business, leadership, entrepreneurship, and global impact.
Jay Adewole and The Winners Circle represent a premium standard for entrepreneurs who want to be seen, heard, structured, and positioned with authority. His work continues to reach founders, executives, business owners, and ambitious builders across media, coaching, publishing, and live strategy.
NBC
FOX
THISDAY
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NEWS CENTRAL
VANGUARD
What the Audience Receives
A premium conversation designed to create movement.
Jay’s strongest sessions connect strategy to implementation. The objective is not to overwhelm people with information, but to help them understand the decision in front of them and what must change next.
Every engagement is shaped around the event objective, audience, format, and the practical value the organizer wants people to take away.
01
Clear business language
Complex ideas are translated into direct, accessible conversations that founders and leaders can apply.
02
Practical frameworks
Audiences receive a structured way to think about the problem rather than another collection of disconnected tips.
03
Decisions and next steps
The session ends with a clearer understanding of what deserves attention and what action should follow.
Signature Speaking Topics
Business conversations built around what founders are facing now.
Every topic can be adapted into a keynote, workshop, panel conversation, fireside chat, executive session, or founder-focused training.
Clarity, Systems & Scale
How positioning, repeatable execution, stronger operations, and leadership capacity create more sustainable business growth.
For entrepreneurs and growth-stage companiesAI Without Losing Strategic Control
How founders can use AI to improve decisions, productivity, follow-up, content, and execution without replacing judgment.
For business, technology, and leadership audiencesBuilding a Business in the United States
Practical insight for entrepreneurs who need stronger preparation, clearer structure, and a credible path from idea to operation.
For entrepreneurs, diaspora, and economic-development eventsVisibility, Authority & Demand
Why expertise alone is not enough and how founders can build a trusted presence across media, publishing, events, and business platforms.
For experts, consultants, authors, and coachesPurpose-Driven Leadership
How leaders make stronger decisions when purpose, commercial discipline, social impact, and long-term direction are considered together.
For leadership, nonprofit, and impact audiences
Engagement Formats
Built for the stage, the boardroom, the podcast, or the screen.
The same strategic perspective can be adapted for different rooms. The format should support the event objective, audience expectations, and the depth of conversation required.
01
Keynote Address
A focused business or leadership message designed to create clarity, challenge assumptions, and move the room toward action.
02
Workshop or Masterclass
A more interactive session that helps participants think through the framework and apply it to a real business challenge.
03
Panel or Fireside Conversation
A moderated discussion that brings practical perspective to leadership, entrepreneurship, systems, AI, visibility, or growth.
04
Executive or Leadership Session
A private conversation for business owners, teams, or organizational leaders centered on one strategic issue or operating priority.
05
Virtual Event or Webinar
A professionally prepared digital session for distributed teams, associations, founder communities, and online conferences.
Jay in Action
Prepared for the room—and focused on the audience.
Live speaking, leadership conversations, and founder-focused events designed to make complex business ideas practical.
Booking Process
Start with the event, audience, and outcome.
Speaking requests are reviewed based on fit, timing, format, location, audience, topic, and the value the event is designed to create.
Fees and logistics are provided after the request is reviewed because each engagement can differ in preparation, travel, format, and scope.
01
Submit the Request
Provide the event, proposed date, location or virtual platform, audience, format, topic, and organizer information.
02
Fit & Availability Review
The request is reviewed to determine alignment, availability, preparation requirements, travel, and the strongest session format.
03
Scope & Booking
Qualified requests receive the proposed topic, format, fee, logistics, agreement, and booking requirements.
04
Event Preparation
The event objective, audience, introduction, schedule, technical requirements, and promotional materials are confirmed before delivery.
Media & Event Resources
Download the official press kit before submitting the request.
The press kit includes approved biographies, introduction, speaking topics, media information, and official photographs.
Speaking Request
Explore Media Information
Tell us about the room you are creating.
Share the event, audience, date, location, format, topic, and desired outcome. The request will be reviewed for fit, availability, scope, and the most appropriate speaking experience.
01
Describe the event.
Include the organization, event title, proposed date, location or platform, and expected audience.
02
Choose the format.
Let us know whether this is a keynote, workshop, panel, fireside conversation, executive session, or virtual event.
03
Define the result.
Explain what the audience should understand, decide, or be prepared to do after the session.
Frequently Asked Questions
What to know before submitting a speaking request.
Detailed scope, fees, travel, logistics, and booking requirements are provided after the event request is reviewed.
Requests may include business conferences, leadership events, founder communities, corporate sessions, panels, workshops, fireside conversations, associations, podcasts, media programs, and virtual events.
No. Fees are provided after the event is reviewed because preparation, travel, audience, format, location, session scope, and related requirements can vary.
Yes. The strongest engagements begin with an existing area of expertise and adapt the emphasis, examples, and audience takeaways to the event objective.
Yes. Virtual keynotes, workshops, founder sessions, panels, interviews, and webinars can be considered when the format and audience are aligned.
The request is reviewed for fit and availability. Qualified requests receive follow-up regarding topic alignment, format, fee, logistics, agreement, and the next booking requirements.