PL3 Virtual Roundtable Recap - How AI Is Transforming Exit Readiness
- William Gladhart
- 14 hours ago
- 4 min read
Roundtable Date: June 26, 2025
Hosted by: The Performance Leadership Learning Lab (PL3) Team
Recap & Introduction
“We backed a great business - we just picked the wrong leader.” This phrase, repeated throughout the investment world, underscores one of the most expensive mistakes in M&A - overlooking leadership and cultural alignment.
The June PL3 Virtual Roundtable brought together a panel of experts to explore how emerging AI tools are transforming how investors, founders, and advisors identify and act on these invisible risks - long before due diligence even begins.
The 45-minute session featured insights from:
Lindsay Guzowski, CEO of The Crucible
Bob Dunn, Managing Director at GF Data, an ACG company
Will Lindstrom, CEO of The Culture Think Tank
Mara Larson-Richard, Head of VC at Salesforce
Together, they shared case studies, personal experiences, and a forward-looking view of how AI - particularly Salesforce’s Agentforce - is helping quantify leadership effectiveness, cultural friction, and execution drag.
From “Data Desert” to Diagnostic Depth
The session opened with a powerful theme: in today’s market, financials alone aren’t enough. Buyers want to understand the people and operations behind the numbers.
Mara Larson-Richard framed it well: “We’ve seen a massive shift in what’s required to fundraise - even at the earliest stages. AI is speeding up how quickly leaders get reps in, test hypotheses, and prove product-market fit.”
But even with financial metrics, leadership often remains a blind spot. Lindsay Guzowski pointed out that most investment materials “offer a paragraph on leadership and a paragraph on culture - yet those are the very areas that impact execution the most.”
The Culture Think Tank’s Will Lindstrom emphasized the importance of surfacing those signals early: “With AI, we can now measure things like leadership alignment and workforce engagement in real-time - and tie them directly to valuation outcomes.”
A Real-World Case: Quantifying Trust and Premium
Will shared a compelling case study in which AI diagnostics played a pivotal role in an exit. A founder-led data tech firm was preparing to sell. Investors were concerned - if the founder exited, would the engineers follow?
Using AI-driven performance data, the leader was able to demonstrate strong cultural cohesion across a multi-generational workforce, leadership continuity, and team resilience. The result? A buyer-specific narrative and a +18% valuation premium.
This wasn’t just about making people feel better - it was about quantifying organizational readiness in a way that inspired buyer confidence.
Surfacing Hidden Risk Before It’s Too Late
When asked about the most common blind spots during exits, panelists were clear:
Leaders often overestimate alignment among teams
Buyers often underestimate cultural friction
Everyone assumes issues will emerge during diligence, but by then, it’s too late.
“Exit is not the time to be surprised,” said Bob Dunn. “You want to know your business inside out - and have the data to prove it.”
He shared a recent GF Data finding: companies that invest in pre-sale quality of earnings reports saw half a turn higher EBITDA multiples than those who didn’t. “That’s because they came prepared - with data and a strong story.”
AI in the Boardroom (And Beyond)
One of the most interesting parts of the discussion explored the growing role of AI in the boardroom. While AI is often associated with automation or customer service, panelists emphasized its expanding value in strategic leadership and decision-making.
Mara offered a real example: Salesforce Ventures-backed companies use generative AI to build dynamic, intelligent board decks - replacing outdated PowerPoints and PDFs with real-time, analyzable narratives.
The takeaway? AI shifts the conversation from what’s happening to why it’s happening - freeing boards and leadership teams to focus on strategic insight instead of chasing spreadsheets.
The Rise of Agentic Organizations
The conversation also explored how AI agents are being embedded in daily workflows, supporting functions from sales to finance to talent strategy.
Mara explained how companies are starting to frame agents not as tools, but as digital team members with names, profiles, and specialties. “We’re seeing orgs where agents handle 90% of initial customer interactions or internal reporting - faster and more accurately than before.”
Lindsay added: “This doesn't mean humans are disappearing. It means the best humans will be those who know how to work with agents - and guide them toward better outputs.”
Exit Planning as an Ongoing Process
Historically, exit prep was a one-time event. With AI, that model is changing. Will Lindstrom explained how platforms like SageForge are helping advisors and wealth managers create living exit strategies.
“Instead of waiting for diligence, advisors can now track readiness every month. It’s real-time, benchmarked, and actionable. That makes exit planning a continuous part of performance management.”
The Human Element Still Matters
One powerful closing insight? Even as AI becomes more capable, people still want to buy from people. Trust, communication, and leadership can’t be fully automated.
“AI is a force multiplier,” said Lindsay, “but it doesn’t replace leadership. It makes good leaders better - and helps everyone stay honest about what’s working and what’s not.”
What’s Next
The PL3 Virtual Roundtable is now a monthly series. Each session will dive deeper into topics at the intersection of leadership, culture, data, and performance, offering practical insights for investors, operators, and advisors preparing for transition or growth.
Register to join live or receive the replay - https://us02web.zoom.us/webinar/register/4017484564097/WN_tXp77fiMS0qb25j-Q13bqg
If you missed our inaugural Virtual Roundtable session or want to revisit the conversation, you can access the full video replay on our PL3 YouTube Channel.
Will Gladhart is the Chief Marketing Officer at The Culture Think Tank & PL3. His experience includes brand strategy & marketing, content creation, email marketing, and communication outreach.