Winning Ways 2024 Recap: Elevating Leadership, Driving the Future of Accounting

110 attendees come together in Chicago for the 3rd Annual Winning Ways Conference 

In the heart of a rapidly changing profession, where firms must adapt to new challenges and opportunities, the third annual Winning Ways Conference stood as a beacon for accounting leaders committed to transformation and growth. With over 55 firms and 110 attendees, this year’s event was a deep dive into leadership development, equipping firms to embrace the future with confidence and vision. 

“Leadership is about shaping the weather of your firm,” remarked keynote speaker Scott J. Allen, driving home a central theme of the event. Strong leadership not only guides firms through uncertainty but creates the climate for growth and innovation. 

Over two days, attendees immersed themselves in discussions on the future of leadership, networking with peers, and actionable strategies to take back to their firms. Here’s a closer look at the highlights and takeaways from one of the profession’s most impactful events of the year. 

Pre-Conference Momentum: Thought Leadership in Action 

Before the official kickoff, attendees had the opportunity to engage in two dynamic pre-conference sessions hosted by event sponsors QuickFee and Karbon. 

• Jennifer Warawa, President of QuickFee North America, presented her insights on building talent pipelines from within. Her session emphasized why fostering leadership development isn’t just an HR initiative—it’s a strategic imperative for sustainable growth. 

• In a compelling fireside chat, Karbon’s CEO, Mary Delaney,  joined Tim Petrey and Megan Roberts from HD Growth Partners (who recently joined the Ascend platform) to discuss how firms are leveraging technology to build inclusive and innovative workplace cultures. 

These sessions set a collaborative and forward-thinking tone, offering attendees the opportunity to get their focus into leadership over the remaining 1.5 days. 

The Conference Kickoff: Visionary Leadership Takes Center Stage 

At 1:00 PM, the main event launched with opening remarks from David Toth – Chief Growth Officer at Winding River Consulting and emcee for this years conference. David then introduced industry heavyweights Allan Koltin and Gary Shamis, who shared their perspectives on the evolving challenges of the accounting profession. 

• Koltin highlighted the importance of leadership alignment and its impact on navigating market pressures and workforce expectations. 

• Shamis reinforced the idea that strong leadership is the linchpin of firm independence and growth, particularly in a profession where change is the only constant 

 The day 1 keynote by Scott J. Allen was a standout moment. His message, “Leaders Control the Weather,” resonated with attendees as a powerful reminder that leadership attitudes and decisions directly shape firm culture, morale, and success. Are you creating a 50^o and rainy environment or 75^o and sunny? 

Next-Gen Leadership Panel: The Future Is Now 

Closing Day 1 was a lively discussion featuring Drew Hendrickson, Lucia Valenzuela, and Brandon Hall. The panel delved into how emerging leaders are breaking the mold, innovating within their firms, and redefining the traditional paths to success. Attendees were buzzing with excitement, many calling this session a game-changer for their perspectives on talent development. 

Bootcamp Energy: Starting Day 2 Strong 

Day 2 opened with a jolt of energy from Matt Terlop, who led 30 participants through a fitness session mirroring the discipline and focus needed to succeed in leadership. 

Managing Partners Panel: Navigating Change 

Leaders Lou Grassi, Larry Autrey, and Beth Leonard explored what it takes to embrace change within the profession. They tackled hard-hitting questions on innovation, talent retention, and how to align leadership teams for long-term success. 

Chief People Officer Panel: Prioritizing People 

A session featuring Danielle McCormick, Kristen Wik, and Erin Stahmer focused on building learning and development into firm culture. The panelists shared actionable strategies for retaining top talent and equating leadership investments to measurable bottom-line results. 

Kristen Wik, Chief People Officer at Centri Business Consulting, also delivered a keynote on how her firm has embedded leadership development into its DNA, proving that prioritizing people pays dividends in both culture and financial performance. 

Beyond the Sessions: Building Connections and Momentum 

Winning Ways wasn’t just about learning—it was about connecting. Between sessions, attendees forged new partnerships, shared ideas, and celebrated the spirit of collaboration that defines the accounting profession. From the lively cocktail reception to spontaneous hallway conversations, the networking opportunities were as valuable as the sessions themselves. 

Key Takeaways: What Leadership Looks Like Today 

1. Leadership Development is a Strategic Imperative 
   Firms that prioritize leadership development see real results, from improved talent retention to increased client satisfaction. 
2. Technology Must Be Central to Your Culture 
   Technology is no longer just a tool; it’s a differentiator. Firms that weave it into their leadership vision stand out in today’s market. 
3. Investing in People is Investing in Growth 
   Building a culture of learning and development isn’t just good for morale—it’s a direct driver of firm success. 

Thank you to our sponsors: 

• QuickFee 

• Paro 

• Miles Talent Hub 

• Karbon HQ 

• Rare Karma  

• Introhive 

Conclusion: Leadership for the Future 

The Winning Ways 2024 Conference reinforced a powerful truth: leadership is the most significant differentiator in the accounting profession today. Attendees walked away with new insights, stronger connections, and actionable strategies to lead their firms into the future. 

As we look ahead to 2025, one thing is certain: the leaders who attended this year’s event are better equipped than ever to shape the weather at their firms and the future of the profession. 

Stay tuned for updates on next year’s event—we can’t wait to welcome even more of you to the conversation.