AI Executive Search Mastermind Summit 2.0

AI IS EVERYWHERE IN EXECUTIVE SEARCH. THE QUESTION IS: ARE YOU ACTUALLY USING IT WELL?

Your team is experimenting with AI. But has it actually changed the way your firm works?

Two hands-on days with executive search leaders focused on turning AI experiments into practical workflows you can actually use.

Chicago

November

through November 4, 2026

The Real AI Challenge

AI ISN’T THE HARD PART.
MAKING IT USEFUL INSIDE YOUR FIRM IS.

Everyone on your team uses AI differently.

You’re trying multiple tools without knowing which really matter.

Great AI demos aren't becoming repeatable workflows.

You wonder what other search firms have figured out that you haven't.

That’s why Chicago exists.

60+ firms

Represented in our AI community

2 days

Hands-on, peer-led working sessions

The people in the room

Practitioners, operators and technology experts.

The summit is shaped by people who work inside executive search and understand that useful AI has to fit the way firms actually operate.

From Experiments to Execution

WHERE YOU ARE TODAY → WHERE YOU LEAVE CHICAGO

Same challenges. A clearer path forward.

Today

Lots of Activity. Little Clarity.

“We should be doing more”

→

↓

SAME QUESTIONS. A CLEARER PATH FORWARD.

After Chicago

Real Progress. Practical Next Steps.

“Here’s what we’re doing next”

Proven Format • Verified Track Record

PHILADELPHIA SOLD OUT.
CHICAGO BUILDS ON WHAT WORKED.

We are not asking you to believe this format works. We already tested it with senior leaders from across the executive search industry.

Philadelphia Participant Survey Ratings

4.8 / 5

Peer Discussions

Highest-rated aspect of the event program

100%

Relevant Content

Rated sessions directly applicable to firm operations

4.7 / 5

Actionable Frameworks

Immediate implementation upon return to office

60 / 60

Seats Sold Out

Full capacity reached weeks ahead of schedule

The real challenge

AI isn't the hard part. Making it useful inside your firm is.

Search firms have access to more AI tools than ever. The harder questions are where each tool belongs, which workflows create real leverage, and how to get an entire team using them well.

Chicago is a working session built around those questions—with peers who understand the practical realities of retained executive search.

A different kind of summit

Not a traditional conference.

You won’t spend two days watching presentations. You’ll compare, test, build and pressure-test practical approaches with the people in the room.

FIGURE OUT WHAT MATTERS

Cut through the explosion of AI tools and understand what’s actually useful in executive search.

BUILD IT

Work with peers on practical workflows across BD, research, delivery and operations.

TAKE IT HOME

Leave with workflows, case studies and implementation ideas you can use with your team.

Built around what you actually use

Your tools. Your workflows. Your case study.

Participants join a cohort based on the LLM they actively use. Each group digs into a real executive search use case and develops a comprehensive case study the full room can learn from.

Workflow labs

Teams of six or fewer

Business development outreach
Search strategy and market mapping
Candidate research and sourcing
Candidate summaries and client updates
Content creation and knowledge capture
CRM, ATS and internal handoffs

Plus practical discussions about CRM/ATS platforms, AI note takers, sourcing tools and how the full technology stack fits together.

The working agenda

Two days. One practical objective.

Leave with a clearer AI playbook and workflows your team can actually use on Monday morning.

Day One

Tuesday · Nov. 3

Build the foundation

Introductions, goals and the state of AI in search
Hands-on AI masterclass led by Joe Ewing
Real executive search applications and working sessions
LLM cohorts begin building comprehensive case studies
Evening cohort collaboration and peer exchange

Day Two

Wednesday · Nov. 4

Turn learning into workflow

AI platforms and executive search technology
Practical tool comparisons across the technology stack
Small-team workflow labs focused on real firm priorities
Cohort readouts, reusable approaches and peer feedback
Implementation planning and clear next steps

What you’ll leave with

Less hype. More clarity. Work you can reuse.

A clearer view of where each major LLM fits
Practical workflows tested against real search work
Case studies and approaches shared across cohorts
A peer network facing the same implementation questions
Concrete next steps for your firm and team

What made the Philadelphia AI Summit valuable wasn't just the technology and use cases. It was the quality of the people in the room.

Marianne McNamara

Founder, Brightview Leadership · Former Head of Operations, ZRG Partners

Chicago · November 3–4

A small-room summit by design.

Participation is capped at 60 to protect the candid exchange, hands-on work and access that made Philadelphia so valuable.

Hilton Chicago O'Hare Airport

Conveniently located inside O'Hare International Airport

Hotel rate: $229 per night

Summit room block available through October 21, 2026

Participant registration

$2,500

$500 deposit reserves your seat and applies to the total.

$1,900 returning participant rate

Available to Philadelphia summit participants.

Limited to 60 participants

A few useful answers

Before you register.

Who is this summit for?

Executive search firm leaders, operations and technology leaders, search delivery professionals, researchers and other people responsible for turning AI into practical firm workflows.

Is this a traditional conference?

No. The format is deliberately hands-on, peer-driven and built around active participation. Expect working sessions, small cohorts and candid exchange—not a parade of slide decks.

Do I need deep AI experience?

No. You should be ready to work, share and experiment. Cohorts are organized around the tools participants already use so the work starts from a practical place.

What should I bring?

Bring your laptop, access to the AI tools you use, and one or two real workflows or firm challenges you want to improve.

Chicago · November 3–4, 2026

Bring the tools. Bring the questions. Leave with the workflow.

60 seats. Two hands-on days. One room built for real exchange.