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

03

November

through November 4, 2026

The Real AI Challenge

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

01

Everyone on your team uses AI differently.

02

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

03

Great AI demos aren't becoming repeatable workflows.

04

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.

Breck Armstrong

17 Oranges

Canay Deniz

Ren Systems

Dan Kalish

Maven Partnership

Joe Ewing

Clarion AI Partners

Manan Shah

Recruiterflow

Trip Flail

JM Search

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.
01

Learn

Prompting, projects, research, analysis, AI agents and the strengths of today's major platform

02

Build

Prompting, projects, research, analysis, AI agents and the strengths of today's major platform

03

Implement

Prompting, projects, research, analysis, AI agents and the strengths of today's major platform

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

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

Day Two

Wednesday · Nov. 4

Turn learning into workflow

What you’ll leave with

Less hype. More clarity. Work you can reuse.

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.

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

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.

Breck Armstrong

Managing Partner at 17 Oranges

Breck Armstrong, Managing Partner at 17 Oranges: A former CIO of Boyden with nearly 20 years of leadership experience in executive search. Breck has led global digital transformation programs spanning AI, automation, and complex M&A integrations. Having operated inside a partner-driven search firm, he understands the commercial, cultural, and operational realities of change. Today, he advises leadership teams on building scalable, AI-ready operating models that improve productivity, protect margin, and deliver measurable technology ROI.

Canay Deniz

CEO and Co-Founder of Ren

Canay Deniz is the CEO and Co-Founder of Ren, the AI-powered relationship intelligence platform that helps client-facing professionals at firms like DSG Global, Riviera, and Klein Hersh, act on the moments that matter in their networks before their competitors do. Prior to Ren, Canay was the US MD at Teralytics, a data analytics company specializing in machine learning. He holds a master’s degree in industrial engineering from ETH Zurich.

Dan Kalish

Director of Recruitment Operations – Maven Partnership

Dan Kalish, Director of Recruitment Operations – Maven Partnership
Based in Maven’s New York office, Dan is the recruitment operations director, focusing on optimizing business activities, streamlining processes, and ensuring the smooth execution of search projects.
With over a decade of experience in finance and a specialized focus on executive search over the past three years, Dan brings a strategic, systems-driven approach to search operations, process optimization, and team development. He plays a pivotal role in refining how top talent is identified and placed, drawing on a deep understanding of the evolving executive search landscape to deliver world-class experiences to clients around the globe. Known for his passion for leadership and professional development, Dan is dedicated to building high-performing teams and fostering a culture of continuous improvement. Before joining Maven, Dan led high-impact search initiatives that reimagined the retained executive search experience for private equity-backed businesses-delivering measurable efficiency gains and elevating client outcomes.

Joe Ewing

Chief Technology Officer at Clarion

Joe builds secure, scalable AI and technology platforms that deliver real-world impact. Over the past 20 years, he has led enterprise and AI modernization across commercial, highly regulated, public-sector, and defense environments, working at the intersection of engineering, governance, and policy to turn complex, high-risk initiatives into trusted, mission-critical systems.

Over the past 20 years, Joe has built, modernized, and scaled complex technology platforms across commercial, highly regulated, and defense environments. His experience includes large-scale enterprise implementations, AI-enabled and data-integrated systems, and modernization efforts supporting mission-critical workflows. His work spans generative AI, advanced analytics, automation, cloud platforms, and enterprise application modernization.

Manan Shah

Co-Founder & CEO of Recruiterflow

Manan is Co-Founder & CEO of Recruiterflow, an AI-native CRM for search firms. Before Recruiterflow, he led his previous software company retention.ai throug a venture round and eventually to an exit via acquisition.

Matt Wright

Founder of Woven Research

Matt Wright is the Founder of Woven Research, where he helps companies build analytics and AI capabilities that improve decisions, reduce costs, and accelerate growth. His work focuses on operating model design, commercial analytics, and AI-enabled workflows that help leadership teams turn strategy into practical, measurable results.
Before launching Woven Research, Matt held leadership and consulting roles with SBI, Maine Pointe, Genesis HealthCare, Newmark, and Grubb & Ellis. Across healthcare, professional services, commercial real estate, supply chain, and private equity-backed environments, he has built a strong reputation for helping organizations improve execution, strengthen visibility, and create competitive advantage through smarter use of data and AI.

Sanket Chauhan

Co-founder of Stardex

Sanket Chauhan is Co-founder of Stardex, an agent-native ATS and CRM built for executive search firms. Stardex helps capture the candidate and client context that often lives in partners’ heads, while automating workflows such as research calibration, client reporting, and database search.

Sanket works closely with search firms on AI-enabled workflows and regularly leads sessions on practical AI adoption. Before Stardex, he was a consultant at McKinsey & Company and began his career as a software engineer.

Stephanie PicoStark

Customer Success | Ren

Stephanie PicoStark brings a relationship-first approach to customer success, helping clients turn technology into practical, everyday value. At Ren, she works closely with firms to support adoption, improve workflows, and ensure teams get meaningful results from the tools they use.

With experience leading customer success at Everlance, Stephanie combines client advocacy, training, and change management in a practical, human-centered way. She holds a Master of Science in Digital Age Learning and Educational Technology from Johns Hopkins University and a Bachelor’s degree in English Writing from the University of Colorado Denver.

At the AI Mastermind Summit, she brings a focused perspective on adoption, user experience, and the human side of AI-enabled workflow.

Trip Flail

Vice President of Information Technology at JM Search

Trip Flail is Vice President of Information Technology at JM Search, where he has spent more than 12 years helping lead the firm’s technology function. Over that time, he has advanced from IT Manager to Director of Information Technology and now serves as a key technology leader for the organization. He brings deep experience in cybersecurity, project management, and enterprise technology operations, and is a Certified Information Systems Security Professional (CISSP).
Before JM Search, Trip held IT leadership roles at Pennco Tech and PayAll Solutions. He is also an active voice in executive search technology conversations, including industry discussions on AI, recruiting technology, and the evolving tech roadmap for search firms.

Dr. Weldon W. Whitener

Founder & CEO of AfterGen

Dr. Weldon W. Whitener is the Founder & CEO of AfterGen, an AI transformation company that helps organisations redesign how work gets done & translate advances in automation & AI into measurable business value.
Dr. Whitener began his professional career after completing a PhD in Bioinformatics at the University of Cambridge, a field combining artificial intelligence & genetics modelling. He spent the next four years at the Boston Consulting Group working alongside FTSE100/Fortune 500 companies helping them use their data & technology to improve decision making, redesign their business processes & drive measurable improvements in their performance. He later joined Amazon where he ultimately became Head of Pricing leading a global team responsible for large-scale transformation initiatives to redesign & standardise processes, harness data & technology & improve pricing decisions at scale.
In 2017, Dr. Whitener founded Afterskills, a global data, digital & AI capability-building company that works with leading organisations to equip their people with the practical skills needed to adopt new technologies & work more effectively in an increasingly data- & AI-enabled environment. He is also an adjunct professor / lecturer at leading business schools including: Harvard Business School, MIT Sloan, Columbia Business School, Oxford Saïd, London Business School, INSEAD, ESADE, IESE & IMD.
Dr. Whitener’s primary focus today is AfterGen where he works with organisations to identify, design & deliver AI-enabled transformations. His approach reflects a philosophy that has been consistent throughout his career: technology creates value when it improves how people & organisations actually work. Rather than simply identifying where AI can be deployed he focuses on bringing processes, technology & people together to redesign how work gets done & apply AI & automation where they can create measurable, sustained improvements in business performance.