Aileron Summit 2026

Get ready to level up how you lead yourself, your people, and your business

Take a step back, connect with other leaders who get it, and lean into topics and sessions that feel pressing to you right now.

Aileron Summit 2026

Get ready to level up how you lead yourself, your people, and your business

Take a step back, connect with other leaders who get it, and lean into topics and sessions that feel pressing to you right now.

Tuesday, September 22 | President’s Retreat

For business owners, presidents and CEOs

Tuesday, September 22 | President’s Retreat

For business owners, presidents and CEOs

8:00 a.m.

Coffee and Connection

Grab a bite, ease into the day, and introduce yourself to people who know what it’s like to carry what you carry.

Play to Thrive: Leading When the Game is Changing

You can’t out-hustle what’s coming. The businesses that thrive over the next two years won’t be the ones playing harder — they’ll be the ones playing differently. In this opening session, we’ll frame the three shifts that matter most for how you lead yourself, your team, and your business, and set up the two days ahead.

Joni Fedders | Aileron

Joni Fedders

President and CEO at Aileron

Dustin Shell | Aileron

Dustin Shell

Chief Operating Officer at Aileron

From the Community: Stories of Impact

Hear authentic stories of transformation from your peers in these community-led breakout sessions:

  • Christy Fox, CEO of Dayton-Phoenix Group shares how to build resilience through the hardest times.
  • Matt Hoying, President of Choice One Engineering on successful successions through unique org rhythms
  • Chad Kuhns, Owner of Kuhns Group on unlocking potential by looking in the mirror and getting on a whiteboard
  • Greg Riley, President of Schaefer on how to make the shift from a paper board to a source of meaningful growth

12:00 p.m.

Lunch

Lunch is yours. Connect with other leaders over a meal, step outside for a walk around the pond, or find a quiet spot to recharge.

In Good Company: Pop-up Peer Groups

The executive seat is heavier than most people around you know. This is a room where you don’t have to translate. Bring the thing you’ve been carrying and spend the session with a small group of presidents wrestling the same weight — grouped live, based on what’s actually on your mind the week of Summit.

Luke Sargent | Aileron

Luke Sargent

Business Coach and Facilitator at Aileron

Eric Wiechart | Aileron

Eric Wiechart

Business Coach and Leadership Coach

The Cost of Waiting: How Fear Quietly Stalls Your Business

There’s a hidden cost in your business, and you won’t find it on your P&L. The cost of chronic pressure and overcommitment is more expensive than you think. This interactive session exposes how fear is keeping your business dependent on you. Then we get to work on changing it.

Erika Alessandrini | Aileron

Erika Alessandrini

Business Coach, Facilitator and Leadership Coach at Aileron

Growing Forward

Before we head into the evening, we’ll take a few minutes to reflect on the day. Real growth is iterative — some things will land, some won’t, and the missing is where most of the learning lives. That’s the work of real leaders.

4:30 p.m.

Off the Clock

The agenda is done. Let’s head outside for drinks, heavy hors d’oeuvres + a light dinner buffet and a golf activity. The best conversations of the day might still be ahead.

Wednesday, September 23 | Leadership Accelerator

For all leaders – teams and individuals

Wednesday, September 23 | Leadership Accelerator

For all leaders – teams and individuals

8:00 a.m.

Coffee and Connection

Grab a bite as you connect more informally with other like-minded leaders in the room.

Play to Thrive: Trust is the New Economy

The game is changing. Trust is the new economy. What you do next is on you. In this closing session we’ll send you into what’s ahead with the room behind you and a clear read on your next move.

Dustin Shell | Aileron

Dustin Shell

Chief Operating Officer at Aileron

LEAD YOURSELF

Pressure Isn’t the Problem: Exposing the Pattern That Keeps You Stuck

You have a pattern. Under pressure, it kicks in — quietly undermining your success, your satisfaction, and your relationships. This session helps you name it, understand what it’s costing you, and experience what becomes possible when you interrupt it.

Erika Alessandrini | Aileron

Erika Alessandrini

Business Coach, Facilitator and Leadership Coach at Aileron

LEAD YOUR TEAM

From Managing to Coaching: Developing a Coaching Mindset as a People Leader

Leadership isn’t about having all the answers—it’s about creating the conditions for others to discover their own. In this session, you’ll learn what it means to think like a coach, shifting from solving problems for your people to developing their confidence, ownership, and capability through powerful coaching conversations.

Wendy Roop | Aileron

Wendy Roop

Facilitator and Leadership Coach at Aileron

LEAD YOUR BUSINESS

Map it to Manage it: A Systems Thinking Approach for Business Leaders

This hands-on working session introduces the core principles of systems thinking and walks through how to map systems and processes. You’ll leave with a practical framework for identifying, documenting, and improving the workflows that drive day-to-day operations.

Dave Allison | Aileron

Dave Allison

Business Coach and Facilitator at Aileron

12:00 p.m.

Lunch

Lunch is yours. Connect with other leaders over a meal, step outside for a walk around the pond, or find a quiet spot to recharge.

Leading in Conflict: How to Show Up for Yourself and Your Team in Hard Conversations

Your team needs healthy disagreement to make good decisions—but many teams struggle to debate productively. In this session, you’ll explore your relationship with conflict and learn how to show up more effectively in the moments that matter most. Leave with practical tools for your next conflict and greater confidence in how you’ll navigate it.

Joni Fedders | Aileron

Joni Fedders

President and CEO at Aileron

LEAD YOURSELF

Why Your Business Depends on You More Than it Should

You built this business, but if you’re honest, it still runs through you. That dependency didn’t happen by accident — and it doesn’t have to be permanent. In this breakout, you’ll unpack how your own choices created it, and learn one shift that offers instant relief.

Luke Sargent | Aileron

Luke Sargent

Business Coach and Facilitator at Aileron

LEAD YOUR TEAM

Accountability That Sticks: What Great Leaders Do Differently

Accountability isn’t about calling people out—it’s about creating an environment where commitments mean something. In this session, you’ll explore why accountability breaks down, assess both your leadership and your organization’s systems, and leave with concrete actions to build trust, ownership, and follow-through.

Erika Alessandrini | Aileron

Erika Alessandrini

Business Coach, Facilitator and Leadership Coach at Aileron

LEAD YOUR BUSINESS

Big B Brand: Seeing Your Brand as a Strategic Advantage

When most leaders think of brand, they think of logos, colors, and fonts —but that’s your little b brand. Your Big B Brand is the collection of thoughts and feelings people carry with them after every interaction with your business. In this session, you’ll explore how a strong brand attracts the right customers, strengthens your team, and sets your business apart.

Grace Jones | Aileron

Grace Jones

Chief Marketing Officer at Aileron

Going Higher

We close where we started — with flourishing. Hear from business owners who’ve lived it and leave reminded of why this work matters.