Chicago Executive Summit

7:45 a.m. - 8:45 a.m.

Strategic Wealth Decisions: What High Achievers Need to Know Before 2026

Presenter: Adam Stock, Founder | The Next Level Planning Group

You’ve built something meaningful—now it’s time to protect and grow it. Join us for a strategic session on key financial decisions successful business owners and executives can’t afford to overlook:

• The Tax Fence Framework – A smarter way to manage tax transitions


• 2025 Tax Law Sunsets – What’s changing and how to prepare


• The Double-Edged Account – Why a top financial tool may be a hidden risk


• Estate Planning Reality Check – Align your intentions with outcomes


• Three Wealth Transfer Strategies – When and how to implement for impact

Topic: Personal Development - Asset & Estate Planning

7:45 a.m. - 8:45 a.m.

Breaking Through the Growth Plateau: Boost Accountability & Impact

Presenter: Christine Watts, Chief of Staff | Ninety

As businesses grow, they reach a point where old methods no longer serve their goals. If you’re finding that your meetings aren’t as productive, your team struggles with accountability, or key decisions don’t have supportive data, it’s time to address some fundamental issues. Explore how mastering three key areas—Structure, Data, and Meetings—can help you break through this growth plateau.

Takeaways:

• Identifying Structure Inefficiencies: Unpack organizational changes needed to unlock greater efficiency and effectiveness.


• Using Data to Drive Success: Actionable steps to implement the right KPIs, and improve team accountability.


• Optimizing Meetings and Strategic Planning: Ensure teams execute on strategic goals aligned with the broader company vision.

Topic: Business Operations - Infrastructure

7:45 a.m. - 8:45 a.m.

Maximize the Transferrable Value of Your Business

Presenter: Mike Silverman, Shareholder & Matt Clark, Shareholder | Dentons

The value of your business has been created through decades of hard work and is typically the largest asset in your personal net worth statement - often representing 80% or more. In this session we’ll define the building blocks for creating, growing and protecting the transferrable value of your business.

We will focus on the proven components of a well-designed exit plan:

(1) Defining goals

(2) Eliminating risks

(3) Protecting the value of the business

(4) Designing Incentive Compensation and Retention Agreements

(5) Creating key value drivers

(6) Implementing a growth plan, a financial plan, a succession plan and an exit plan

Topic: Personal Development - Exit Planning

7:45 a.m. - 8:45 a.m.

Ownership Transition Alternatives: ESOPs in Long-Term Planning

Presenter: Tom DeSimone, Managing Director | Prairie Capital Advisors

Business owners evaluating transition options must consider goals, market conditions and timing. While many paths exist, each has distinct pros and cons. Among them, ESOPs (Employee Stock Ownership Plans) are often misunderstood or overlooked. This session will provide a clear, practical overview of how ESOPs work, their strategic advantages and how they compare to other ownership transition alternatives. We’ll also address common myths and misconceptions to help you make informed decisions. Whether you're starting succession planning or actively evaluating exit strategies, this discussion will offer valuable insights to guide your next steps.

Topic: Financials - Mergers & Acquisitions

7:45 a.m. - 8:45 a.m.

The CEO's Guide to Strategically Scaling Sales

Presenter: David Mullins, Strategic Sales Coach | SalesStar

Unlock the secret to scalable, measurable, and predictable sales growth in this exclusive session designed for CEOs. Learn how to build a strategic sales system that drives consistent results and empowers your sales force.

Attendees will leave with actionable takeaways:

• Proven methodologies to streamline sales processes and drive consistent results.


• Strategies to leverage data for better decision-making and measurable outcomes.


• Insights to achieve sustainable growth and elevate your company's performance.

This session is for CEO's who want a clear path to building a strategic sales system that is scalable, measurable, and predictable.

Topic: Customer Engagement - Sales

7:45 a.m. - 8:45 a.m.

The Million-Dollar AI Gap: Are You on the Wrong Side?

Presenter: Steve Russell, Founder & CEO | Upstart 13

Most companies think they’re leveraging AI because they use ChatGPT. That’s shortsighted. AI isn’t just a tool—it’s reshaping industries, redefining competition, and widening the gap between leaders and laggards.

The hard truth? Scattered AI use—like chat features—isn’t a strategy. Are you on the wrong side of AI transformation? This session will give you clarity and direction.

In this session, you will:

✔ Assess your AI maturity and identify gaps.

✔ Learn why most AI initiatives fail—and how to succeed.

✔ Walk away with a clear AI roadmap for measurable impact.

Move now, or watch your competitors take the lead.

Topic: Business Operations - Technology

12:30 p.m. - 1:30 p.m.

Unlocking Business Value: A CEO’s Guide to Exit-Ready Growth

Presenter: Paul J. Brahim, Managing Director, SVP - Financial Advisor | Wealth Enhancement Group

Most business owners don’t plan to sell tomorrow—but the smartest ones prepare as if they might. Whether you're 2 years or 10 years from stepping away, the decisions you make today will shape your future options—and financial outcomes.

In this session, Paul Brahim shares a 6-step framework to drive value, align your business with personal goals, and ensure you’re ready when the time comes.

You’ll walk away with tools to:

• Assess and grow the value of your business


• Align personal wealth goals with business strategy


• Identify and enhance key value drivers


• Evaluate potential exit options


• Build a business that’s ready to sell—even if you're not ready to exit yet

Topic: Financials - Financial Management

12:30 p.m. - 1:30 p.m.

The Dark Side of Private Equity: Missteps that Could Cost You Millions

Presenter: Brian Daley, Director of Strategic Partnerships | Founders Advisors

With more PE firms targeting private companies, business owners must be equipped to navigate this complex world successfully. Using case studies, data-driven insights, and over two decades of M&A experience, we’ll discuss the PE investor ecosystem, how they exploit inexperienced business owners, and strategies to help you protect your equity.

You’ll learn:

• 7 reasons your business is not qualified for PE investment (and what to do)


• Essential questions to answer before engaging PE


• The truth about “Minority Investors” and “Founder Aligned” PE


• Why 90% of founders lose in PE negotiations


• Enterprise Value Coaching through Industry Driven Valuation Scorecards

Topic: Financials - Mergers & Acquisitions

12:30 p.m. - 1:30 p.m.

CEO's Candid Guide to Right People, Right Job, Right Fit To Scale the Business

Presenter: Mike Hall, Executive Advisor | Culture Index

Join the Culture Index team to reveal the true fit of your executive team and leaders- who is in the right seat and who is not? Do you have the right team in place to scale your business? Not getting the top and bottom line growth by not hiring and obtaining the right team? In this session, you will be prepped to utilize data to make more objective human decisions in securing the right talent in order to drive sustainable growth. Walk away with new insights, tips, and practices to implement into your business and better align your people.

Topic: Leadership - Retention & Engagement

12:30 p.m. - 1:30 p.m.

Grow Profits Through Process Automation

Presenter: JJ Russell, Director of Sales | Vsimple

Generative AI is transforming how businesses scale and operate - but most leaders lack a clear path forward. In this session, you’ll get an executive playbook to drive immediate ROI with AI-powered automation. Learn how to cut manual work, reduce costly errors, and gain real-time visibility to grow faster.

You’ll walk away with:

• A CEO-level understanding of why clean, connected data matters


• Real-world examples of AI unlocking efficiency and capacity


• A tactical roadmap to implement automation - fast, without disrupting your team

Topic: Business Operations - Technology

12:30 p.m. - 1:30 p.m.

Winning the Game: Handling Unsolicited Private Equity Offers Like a Pro

Presenter: Andrew Hansen, Founder-Owned Investment Banking Advisory | William Blair

If a private equity firm made an unsolicited offer to buy your business, would you know how to respond? Many business owners face this situation but struggle determining whether an offer is fair, competitive, or even worth considering.

The challenge lies in the information gap and private equity has the competitive edge. Without a clear game plan, business owners risk selling for less —or walking away from a game-changing deal.

Key takeaways:

• How to assess an unsolicited offer and craft a strategic response


• Where to find reliable market data—and how to leverage it


• Proven negotiation tactics to level the playing field

Topic: Financials - Mergers & Acquisitions

12:30 p.m. - 1:30 p.m.

Reaching New Heights: Unlocking Six Financial Functions for Growth

Presenter: Haleh Fardi, Founder & CVO | ProCFO Partners

Your company started with an idea, and as it’s grown you face different challenges. Do you have the insights and people needed to make informed decisions to grow strategically? 

In this session, we discuss the six financial functions your company needs in order to continue your ascent. 

You will learn:

• The six essential financial functions that every business needs to grow.


• The difference between financial functions and financial responsibility.


• What your business might be missing in terms of the financial skill set and framework required to grow.

Topic: Financials - Financial Management