A community for senior AI professionals AND THE AI Curious

AI 5essions is an exclusive and free 5 person event designed specifically for senior AI professionals and the AI curious. This midday virtual gathering is dedicated to fostering connections, camaraderie, and insightful conversations among leaders in the AI space and those working to understand how to implement AI successfully.

5 stars

“Very interesting and thought provoking discussion on AI and Product Management…”



Share insights, challenges, and triumphs with your peers from multiple sectors of the AI industry


Honest, open conversation guided by an expert facilitator while keeping a casual, fun vibe


Going beyond a traditional “professional” event and creating genuine friendships with like-minded AI leaders

Hear from an attendee
A community to call your own

Whether you’re working in product development, community strategy and management, customer support, or customer success, you face many of the same customer centricity challenges every day that so many others do. Wouldn’t it be great to have some time aside from the daily grind to share, vent, learn, celebrate, and get inspired? In retrospect it seems obvious; we need a space to speak openly and honestly with our peers. We need a place to nerd out with people like us. 

That’s how AI 5essions was born. 

A peek into the event

SEnior peers

Everyone who joins an AI 5essions event has been fully vetted and each event has a uniquely curated group of 5 attendees. 

Attendees work at everything from startups to Fortune 50 companies and are chosen to ensure a great conversation. All attendees are highly experienced practitioners that have great things to add. 

Invitations are for individual events but events often include returning attendees.

Virtual & Facilitated

Each event lasts 2 hours and is scheduled midday in the Central time zone.

Discussions are driven by the interests and needs of each unique event group, but past topics have included:

✔ How to manage the hype and demands vs tangible business results

✔ Integration of AI tools into customer support processes

✔ Legal ramifications of AI content issues

✔ How to build AI tools as well as processes and workflows that avoid societal and emotional biases

✔ The boundaries and opportunities between human creativity and AI efficiencies 

Tasty Snacks

Every attendee receives a box of tasty curated snacks that they can eat during the session. It’s an excellent way to make a fun virtual session into a fantastic community experience. 

Each item in the snack box is specifically chosen to create interesting pairings and flavor combinations. 

You never know what unique and sometimes odd snacks you might get, but a dash of bourbon sea salt or a dip in local mint honey will delight your taste buds!

5 stars
“Very interesting and thought provoking discussion on AI and Product Management. Jake as the master facilitator did a great job getting everyone involved and sharing their ideas and perspectives. I highly recommend these sessions!”

Cesar Castro
Sr. Product Manager Automation Services @ Salesforce
5 stars
“Well played, Virtasant… empowering one of the best connection-building professionals in the tech and community space (Jake McKee) to host a thoughtful session on AI and AI-integration. This was a great experience. The snacks were delightful, the conversation inspiring, and the participants were a dream to meet. I look forward to what the future holds for AI 5essions!”

Izzy Neis
Head of Digital @ ModSquad

5 people.
Infinite connections.

AI 5essions is a gathering the Virtasant team hosts once a month online at no charge to the attendees. Each event is designed as a small group, no-sales session where the focus is solely on AI discussion and ideas and powered by a delightful box of tasty snacks. After all, what better thing to bring smart people together and get them talking than food?

Who’s going to
be there?

The invitation list for each and every event ensures a well-balanced, non-competitive group of five people in a relaxed and welcoming atmosphere that allows participants to feel comfortable—and talkative. Great connections come from great conversation, and AI 5essions encourages positive, safe, frank, and open discussion around topics we all care about.

Why 5?

It’s the perfect number of people. We enjoy the intimacy and power of a small group, but enough variety of opinion to drive innovative insights and unexpected outcomes. The goal is to come away with a sense of support, camaraderie, and understanding—the unmistakable feeling that you’ve connected with someone who gets you, knows what you’re going through, and can help you along the way.

The universal language of community.

Nothing brings people together like a good bite to eat. Since we were little children, we’ve been gathering around the table with family and friends to share a meal. So we strive to make AI 5essions a unique community experience by creating a custom menu of tasty noshes delivered to your door.

Get Invited.

As the name suggests, there are a limited number of seats for each AI 5essions event. We curate the guest list to ensure there are no conflicts of interest and that we’re forming a great group of peers. If you’re interested in joining us, please fill out the form below. If you’re a fit for the event, we would love to host you at AI 5essions soon.

Are you an customer centricity practitioner doing great work in product management, community, customer support, or customer success? Check out CX 5essions! The same great 5 person, virtual, snack-fueled event that has makes AI 5essions so much fun.


AI 5essions is a free event for attendees, made possible by our wonderful sponsors who understand that the best way to connect with potential customers is through direct support of community events. AI 5essions wouldn’t be possible without the amazing support of the folks at Virtasant. Their team has been been working in the public cloud since its inception in 2006, blending proprietary technology, deep expertise, and one of the world’s largest networks of cloud professionals. Skills that are absolutely required for the growing AI demands!

Sign up for AI 5essions!


For information about my Community Consulting, Training and Speaker services, or to find out more about Dinner5, my unique community for community builders, contact me today.

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