The accounting profession isn’t evolving gradually... it’s shifting in real time.
At this year’s Digital Deep Dive Summit, held March 12–13 in Chicago, marketing professionals and firm leaders came together to explore what it takes to grow in an environment shaped by AI, private equity, and rapidly evolving client expectations.
Curated and founded by David Toth, President and Chief Growth Officer at Winding River Consulting, Digital Deep Dive has grown into a community built around one central idea: helping firms think more intentionally about growth.
This year’s theme made that idea explicit:
Growth by Design. Not by Reaction.
The summit opened with a hands-on look at how firms are actually using AI today. Not in theory, but in practice.
From workflow automation to content creation to rapid application development, David Toth (CGO, Winding River Consulting) and Adam Klein (Head of Industry, Advisory, Introhive) demonstrated just how quickly AI is lowering the barrier to capability. Tasks that once required significant time, cost, and technical expertise are now accessible to firms willing to experiment.
But alongside the excitement came a clear tension: tool overload.
Firms are trying many things but not always implementing them deeply. AI adoption is no longer about awareness. It’s about discipline—choosing where to focus and executing with intention.
This session quickly surfaced one of the most immediate growth opportunities in the profession: existing clients.
Despite offering a wide range of services, most firms still average just over one service per client. Timothy Keith (CEO, Propense) raised a critical question: Why are firms investing so heavily in new client acquisition when so much growth already exists within their current relationships?
“The industry is trained to be perfectionists. And perfectionism is a weakness in business—because if you’re not executing, you don’t learn.” - Timothy Keith
The answer isn’t process—it’s mindset. Cross-selling is not a sales problem. It’s a cultural one—and it requires leadership to solve.
This session with Sam Pagel (COO, Resound) and Jason Hendrix (Director of Digital Marketing, Resound) explored the concept of a “digital twin”—AI-powered extensions of individuals that can replicate voice, thinking patterns, and expertise.
While provocative, the session pointed to a deeper reality: AI is not just changing how work gets done. It’s beginning to change how people scale.
For accounting firms, this raises important questions about content, thought leadership, and how expertise is delivered. The takeaway is this: firms need to start thinking about how their people and their ideas can scale beyond traditional constraints.
After a break for lunch, David Toth officially opened the 5th year of Digital Deep Dive by grounding the room in the purpose behind the conference. At its core, the event is about creating space for honest, strategic conversations—ones that challenge how firms think about growth, not just how they execute it.
That framing carried through the entire event.
The highly anticipated fireside chat with David Cohen (Chief Sales Officer at HubSpot), and Brendan Walsh (Co-Founder and Chief Revenue Officer, Mole Street), brought an operator’s perspective to how quickly growth itself is changing.
AI adoption hasn’t been gradual. It’s been exponential. Within a year, HubSpot saw usage jump from roughly half the company experimenting with AI tools to nearly full adoption across teams. But the real shift isn’t adoption, it’s performance.
The gap between those using AI effectively and those who aren’t is already measurable in output, efficiency, and results.
“The people embedding AI into their workflow… are the ones who are actually winning.” - David Cohen
That shift is forcing a rethinking of how growth teams operate. In some organizations, the goal is now clear: remove everything that isn’t customer interaction.
“80% of time should be spent in customer conversations… everything else is automated.”
Prospecting, follow-up, note-taking, forecasting—much of it is already being handled by AI. At the same time, how firms get found is changing just as quickly.
Search is shifting from traditional SEO to AI-driven discovery, where fewer searches produce significantly higher-quality leads.
“The quality of those searches is astronomically better… conversion rates are 3x higher.”
Which leads to a counterintuitive reality: Websites matter more than ever—but not because people visit them. They matter because AI systems rely on them to decide whether your firm shows up at all.
The CEO panel surfaced one of the most important tensions facing firms today. How do you drive innovation inside organizations that are built to minimize risk? As David Toth framed it, firms are trying to be intentional about growth, but they’re doing it in environments where change is naturally resisted.
From there, the conversation moved quickly beyond theory into how growth actually happens inside firms. For many leaders, it starts with strategy, but not as a document, as a filter for decision-making.
“Everything we do is focused around that strategy… What are we trying to solve? How are we going to measure it?” - Suzanne Forbes (CEO, JMCO)
Even with strategy in place, execution runs into a more human challenge: People.
Accounting firms are wired for precision, consistency, and risk management, not rapid experimentation.
“95% of our team… does not like risk, does not like change.” - Brandon Hall (CEO, Hall CPA).
That creates friction when growth requires trying new approaches, adopting new tools, or moving faster than the organization is comfortable with.
Some firms are addressing this structurally bringing growth closer to leadership and reducing layers of approval. Others are taking a more pragmatic approach: testing ideas quietly, proving results, and scaling them once success is visible.
“Sometimes ideas have to marinate… you don’t succeed at first, bring it back.” - Suzanne Forbes (CEO, JMCO).
But across every perspective, one idea stood out:
“AI collapses workflow. What do we sell? Workflow.” - Brandon Hall
That reframes the challenge entirely. If AI reduces the need for traditional workflows, firms can’t rely on optimizing what they’ve always done. They have to rethink what they offer and how they create value.
Day 1 concluded with a cocktail reception and sponsor dinner hosted by Mole Street, Introhive, Resound, and Propense.
As always, these networking opportunities are where many of the most candid and valuable conversations happen, reinforcing the collaborative nature of the Digital Deep Dive community.
Day 2 opened with a big-picture view of the accounting profession from industry pioneer and expert, Gary Shamis (CEO, Winding River Consulting).
The message was clear: the industry is undergoing structural change. AI, private equity, and shifting client expectations are not isolated trends. They are interconnected forces reshaping how firms operate and compete.
At the same time, this disruption is creating opportunity—particularly for firms willing to be intentional about how they position themselves. This is not a temporary shift. It’s a long-term transformation, and firms must plan accordingly.
“Think of your firm like a Chick-fil-A. Create an environment so comfortable for your clients that you build a relationship. That’s the sustainable differentiator.” - Gary Shamis
Senior Executive Consultant for Winding River Consulting, and owner of Winsome Marketing, Joy Youell focused on how AI is changing not just internal operations—but how firms are found.
As search evolves from traditional SEO to AI-driven discovery (AEO/GEO), firms must rethink how they create and structure content. The implication is significant:
Visibility is no longer just about ranking—it’s about being understood and surfaced by AI systems. Firms that adapt their content strategy early will have a meaningful advantage in how they are discovered.
This session by Brian Blaha (Managing Director, Advisory, Winding River Consulting) brought the conversation back to fundamentals: alignment.
Growth, profitability, and enterprise value are not separate conversations—they are directly connected. Firms that lack alignment across leadership, compensation structures, and long-term strategy struggle to build real value.
The distinction between market compensation and ownership return was particularly important, highlighting how many firms unintentionally limit their own enterprise value. You cannot build enterprise value without strategic alignment. And alignment must be intentional.
Across every session, one idea remained consistent: The firms that succeed will not be the ones that react the fastest. They will be the ones that act most intentionally.
Digital Deep Dive 2026 reinforced that growth is not something that happens by default. It requires clarity, alignment, and leadership.
To our attendees, speakers, and partners—Mole Street, Introhive, Resound, and Propense—thank you for contributing to a candid, thoughtful, and forward-looking event.
The conversations don’t end here. They’re meant to be carried forward—into your strategy, your team, and your next phase of growth. Because growth isn’t something that happens to you. It’s something you design.
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