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Inaugural Winning Ways Event: A Recap

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This year for the first time, close to 100 practice leaders and managing partners convened in Chicago on November 1-2 for Winning Ways.

Originally scheduled to launch in 2021, the conference endured a COVID-19-related delay and took place this month in the windy city.

The inaugural conference was an outstanding success. Attendance and feedback validated what creators Allan Koltin, Gary Shamis, and David Toth had intended: to present an unrivaled professional development opportunity for leaders of accounting firms.

Gary Shamis describes it this way: “There isn’t anything like this and bringing together a small group of Top 100, progressive, mid-tier, and future-thinking entrepreneurial firms was an incredible experience for all involved. No doubt everyone was able to bring back ideas, relationships, and feedback to their firms. We look forward to continuing this in 2023.”

A Winning Event

The result was two days of dedicated space for elite professionals to focus on contemporary topics, convening for expert insights, actionable content, and powerful connections.

Co-facilitated by Koltin Consulting and Winding River Consulting, attendees enjoyed accounting-specific keynotes, intensive breakouts and panels that unpacked the biggest issues facing the profession at the moment.

Allan Koltin explains, “Never have we seen so much change in public accounting as we’ve seen in the last 2.5 years. This conference brought together the industry’s most prominent thought leaders to tackle the most pressing issues: talent acquisition and retention, the pros and cons of private equity, and process/automation.”

These critical topics were front and center at the conference: 

  1. Mergers and acquisitions with sessions on private equity, industry activity, and mega-mergers.
  2. Talent attraction and capacity with sessions on practice management, outsourcing, and process improvement and optimization.

Speakers included:

  • Allan Koltin, CEO of the Koltin Consulting Group
  • Gary Shamis, President and CEO of Winding River Consulting
  • David Toth, Chief Growth Strategist of Winding River Consulting
  • Allan Fisher, President of Premier Financial Search
  • Michelle Mahle, Tax Operations and Innovation Leader, Shareholder at Elliott Davis

Here is a brief summary of high-value takeaways from Winning Ways 2022.

M&A, PE, and the Future

The world of accounting has been disrupted by what some are calling a “transaction frenzy.” Attendees heard firsthand from leaders on the frontlines of seismic shifts in M&A and PE in the industry. They were given the big picture of what is currently happening, and what is forecast for 2023 and coming years. Key takeaways were conveyed for the most strategic responses to these disruptive dynamics, and how to adapt business models in the face of shifting markets.

Dealing With the Challenges of Human Capital

It is perhaps the foremost issue on every accounting firm leader’s mind at the moment: how to manage the challenge of attracting and retaining top talent. Numerous partner agencies and specialists were brought in to present on this topic. These presentations supported high-impact, peer-driven conversations around growth and the operational needs necessary to safeguard and scale a workforce.

  • The session with Michelle Mahle from Elliott Davis covered tax operations and the importance of investing into infrastructure and process.
  • The session with Allan Fisher centered on the changing landscape of the profession and remote work opportunities and challenges. This included specific tactics for attracting and retaining talent from an HR perspective. Pay scales are shifting, expectations are shifting, and the opportunity is shifting across all landscapes (physical and non-physical).
  • Gary Shamis then presented on big challenges leaders face culling clients, raising fees, and having difficult conversations. His compelling presentation delineated the strategies that make a practice more profitable and scalable.

An Outsourcing Panel like None Other

For actionable solutions to the many challenges of human capital, three strategic partners were featured on an outsourcing panel:

  • Trigger is a South Africa-based, global outsourcing partner. Their leader discussed the ways in which they provide tools to support extraordinary human talent and key performance enhancing technology.
  • SurePrep works with three of the Big 4 and thousands of other firms across the U.S., providing tax automation software and more. They brought a strategic understanding of how automation and technology will typify the future of work environments.
  • Paro exists to unlock the future of accounting, offering a growth platform that is innovating ways to empower the talent and tools for the next season of firm development.

Each of these companies plays a different yet critical role in a firm’s need to make outsourcing a part of human capital strategy going forward. 

Chase Birky, CEP + Co-founder of DarkHorse CPAs reports, “On top of the insightful content and commentary covered by the speakers, I found a ton of value in being able to develop relationships with the caliber of people you don’t often get the opportunity to cross paths with at other conferences, facilitated in a curated environment that made it natural to have stimulating conversations.”


Winning Ways attendees included leaders from Top 200 firms, progressive mid-sized firms, and innovative entrepreneurial firms, including the following:

  • Marcum
  • Cbiz
  • Cohen and Company
  • Wipfli
  • LBMC
  • Bennett Thrasher
  • KBKG
  • GHJ
  • Porte
  • Blue
  • MGO
  • Brown Edwards
  • Grassi
  • Whitley Penn
  • Elliot Davis
  • Forcis
  • Eisner
  • Smith + Howard
  • Mowery
  • Krost
  • Laauterbach
  • Brinker
  • Dark Horse
  • HD Davis
  • Hall CPA
  • And more

A special thanks to event sponsors, which included Tri-Merit, Introhive, Premier Financial Search, and Aiwyn.

To learn about our next Winning Ways conference, click here.

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