Leadership in the AI Age

Helmwise AI Captain’s Cohort™

Clarity. Wisdom. Practical AI Strategy for Modern Leaders.

A Leadership Experience Built for the AI Era

The Helmwise AI Captain’s Cohort™ is a leadership experience designed for business leaders navigating the realities of the AI age. Hosted in Knoxville, Tennessee, this Cohort brings together Captains seeking clarity, alignment, and practical ways to apply AI within their organizations.

Through guided discussions, expert insight, and peer collaboration, participants step away from daily operations to gain perspective and return with actionable strategies to lead with confidence in a rapidly changing landscape.

Our keynote speakers

With over a century of combined experience in leading enterprises of all sizes, we believe in multiplying the blessings that experience has bestowed on us, as well as the company of Captains who have traveled before us. We lead with humility and are candid about our failings, but are earnest about the sharing of knowledge, wisdom, and insights to minimize shipboard turbulence and bring peace of mind to business Captains.

Together with a growing cadre of subject matter experts, who we call Helmwise Fellows, we partner with sea-worn leaders to help you remove dysfunction, scale operations, and galvanize and preserve organizational cultures so you can best serve those you lead.

Hosted in Knoxville, TN

The Helmwise AI Captain’s Cohort™ takes place in downtown Knoxville, Tennessee, a city that blends historic character with modern energy in the foothills of the Great Smoky Mountains.

Participants will stay at The Tennessean Hotel, a refined downtown retreat offering luxury accommodations and personalized service, located just a short walk through World’s Fair Park to the Convention Center. This setting is intentionally chosen to support clarity, connection, and focused leadership in the AI age.

Knoxville, Tennessee

What You’ll Gain

The Helmwise AI Captain’s Cohort™ is designed to be both practical and collaborative, helping leaders gain clarity on how to approach AI within their organization and understand where it creates real value. Through guided discussions, peer collaboration, and sessions with leading thinkers and practitioners, participants strengthen decision-making and build confidence to lead their teams through change.

Each participant will also develop a personalized AI agent prior to the event, providing a tangible tool to support ongoing productivity and daily leadership. The experience is intentionally interactive, combining roundtables, small group sessions, and large group teaching to create meaningful dialogue, shared insight, and practical application.

Future Dates

Join the Helmwise AI Captain’s Cohort™

This is a moment that requires thoughtful leadership. The Helmwise AI Captain’s Cohort™ equips you with the clarity, tools, and relationships needed to lead well in the AI age.

May 28 - 31, 2026

Join us this May for a
Helmwise AI Captain’s Cohort™ Experience.

Nov. 17 - 19, 2026

Join us this November for a
Helmwise Cohort™ Experience.

Nov. 10 - 12, 2026

Join us this November for a
Helmwise Cohort™ Experience.