Earlier this month, accounting firm leaders in the accounting industry gathered in Chicago for the fourth annual Digital Deep Dive Summit hosted by Winding River Consulting. Over two dynamic days, attendees explored the theme ‘Growth Unlocked for the Digital Era’, with wide-ranging discussions on everything from the impact of Generative AI to the state of the accounting industry.
The event drew 45 attendees from leading accounting and advisory firms, as well as a range of consultants and seasoned industry experts. The firms represented ranged from entrepreneurial firms making a big splash in the digital arena to well-established top 50 firms focused on building digital strategies at scale.
The summit began with an insightful, timely session from Franco Valentino, Founder & CEO of Narrative SEO. Franco explained the changing nature of search, explaining the increasing role of zero-click searches and the impact these are having on firms’ website traffic. He shared a case study of Minc Law, highlighting the firm’s SEO journey and how they navigated Google algorithm updates. Franco ended his presentation by outlining how firms are taking a new approach to analytics to build smarter funnels that help them level up their approach to generating leads on their digital platforms with a more robust attribution and reporting tool set.
After this, attendees heard from Mike Jones of Resound Creative, who shared the highlights from Resound’s most recent Remarkabrand Index for Accounting Firms. With insights from this analysis of nearly 1,500 accounting firms, Mike shared a series of best practices that firms can adopt to differentiate their brand from the competition.
Following a break for a catered lunch and networking, Aaron Minc of Minc Law gave a candid presentation where he discussed his journey building Minc Law from zero to a firm that generates hundreds of organic leads every month.
Aaron discussed at length how the way his firm approaches SEO has evolved over the years. From building out an in-house content operation to rebounding from Google algorithm updates that cut his traffic and lead flow in half, Aaron pulled back the curtain on how a high-performing digital marketing operation functions.
Moving forward, Aaron explained why he’s focusing on diversifying his firm’s digital marketing efforts, sharing his perspective on how he’s approaching LinkedIn, the business impact of going viral on TikTok, and why he’s focusing so heavily on content that closely matches search intent.
After a quick networking break, attendees enjoyed round table sessions with our presenters and sponsors. Over an hour, attendees rotated through various tables, getting the opportunity to connect with thought leaders like Brandon Hall of Hall CPA and Jon Hubbard of Boomer Consulting.
Day 1 ended with a session led by Gary Shamis, CEO and Founder of Winding River Consulting. As one of the most influential figures in accounting, Gary offered attendees his view on the state of the industry, focusing on the pressures firms face in staying independent, navigating private equity, and building for long-term success in an ever-more challenging environment.
With plenty of audience interaction, questions, and deep insights on themes including leadership, succession, and alignment, Gary’s presentation encouraged attendees to question the bigger strategic questions that drive the success of their firm over the long term.
Day 2 kicked off with a session led by David Toth, Chief Growth Officer at Winding River Consulting. In this session, David shared exclusive findings from Winding River Consulting’s inaugural executive survey, offering attendees a high-level overview of how the industry’s leading firms are approaching strategic challenges like organic growth, pricing, compensation, and technology.
This was followed by sessions from two more sponsors, Mark Hansen, CEO & Founder of Rare Karma, and Adam Klein, Head of Industry, Accounting & Advisory at Introhive. Together, Mark and Adam discussed the emerging trends they’re seeing in the world of Customer Relationship Management and shared the tech-first approaches that firms are taking to build closer relationships with their existing and prospective clients.
Next, attendees heard from Ross Henderson, Head of Content Operations at Winding River Consulting. Ross shared a series of technology wins, fails, and opportunities that his team is seeing across the industry. He covered five key areas: CRM Platforms, Analytics & Reporting, SEO & Content, Email Marketing, and Social Media, and shared several practical use cases for firms to adopt AI technologies in their digital processes.
After a short networking break, David Toth hosted a panel discussion with three guest speakers: Stacy Dreher, Chief Growth Officer of James Moore, Jon Hubbard, Chief Growth Officer of Boomer Consulting, and Brandon Hall, Managing Partner of Hall CPA. This wide-ranging discussion covered how firms can measure digital performance, communicate its impact, and recruit digital evangelists that accelerate adoption.
As leaders of firms with thriving digital strategies, the panelists shared their reflections on how they’ve successfully integrated digital into their firms’ growth cultures, explaining how they secured buy-in across their firms, reflecting on the challenges they’ve overcome, and offering actionable tips for firms that are just beginning their digital transformation journeys.
The summit concluded with a discussion centered on paid media strategies. Digital leaders from a variety of firms shared what’s working for them, how they’re allocating budget towards paid efforts, and the metrics they're using to evaluate success.
With insights ranging from the tactical elements of building campaigns to strategic discussions on channel selection, this session offered attendees an invaluable window into how their peers are approaching paid media in 2025.
The 2025 Digital Deep Dive Summit didn’t just explore the most pressing issues facing digital leaders in the professional services industry; it provided attendees with a playbook of actionable strategies they could take home and adopt to position their firms for success. Attendees brought an open mindset, plenty of ideas, and a willingness to share what they’re working on, making Digital Deep Dive an invaluable forum for growth leaders across the industry.
We’d like to extend our thanks to all of our attendees, as well as our partners and sponsors: Resound Creative, RareKarma, Introhive, and the Association for Accounting Marketing. We’re already excited for next year’s Digital Deep Dive Summit and look forward to welcoming everyone back. If you’re interested in learning more about attending next year’s event, we encourage you to register your interest here.
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