In this episode of The Private Equity Podcast, Alex Rawlings is joined by Dan Bernoske, Founder and CEO of Cortado Group, to explore how private equity firms and portfolio companies can strengthen go-to-market performance while effectively leveraging AI.
Dan explains why speed matters after an acquisition, particularly when assessing commercial talent, and why firms need to separate emotional attachment to legacy teams from objective performance data. He also explores the importance of treating CRM systems as strategic infrastructure rather than simply another piece of technology.
The conversation then turns to AI. Dan shares practical applications for using call transcripts to coach sales teams at scale, improve qualification, identify performance trends, and ultimately increase win rates. He explains why successful AI adoption starts with the business problem—not the technology—and why portfolio companies should build a strong proprietary “context engine” around their CRM data, call transcripts, buyer personas, and historical wins and losses.
Dan and Alex also discuss how AI is changing organizational design, allowing salespeople to spend more time building relationships with buyers while technology handles lower-value tasks. Crucially, Dan warns against viewing AI as a replacement for human salespeople: poorly deployed automation can damage relationships and even burn entire territories.
Key Takeaways
• Move quickly when evaluating commercial talent, but understand where founder-led strengths still create value.
• Build the sales process first and configure the CRM around it—not the other way around.
• CRM data integrity is essential for reliable pipeline visibility and forecasting.
• Use AI to analyze sales calls, improve qualification, and deliver coaching at scale.
• Create a proprietary context engine before becoming overly dependent on any single AI model.
• Redesign roles by identifying tasks AI can handle while allowing people to focus on empathy, listening, trust, and relationships.
• Don’t automate bad processes. Strong sales fundamentals remain essential regardless of the technology.
Timestamps
00:00 – Introduction to Dan Bernoske and Cortado Group
00:57 – Where PE firms and portfolio companies move too slowly
02:54 – Warning signs that commercial talent needs replacing
04:37 – Three fundamentals of an effective CRM
06:34 – How AI can transform go-to-market strategy
08:21 – Using AI to analyze sales calls and coach teams
09:46 – Measuring qualification frameworks such as BANT
11:45 – ChatGPT, Claude and choosing AI technology
13:14 – The three foundations for successful AI implementation
13:40 – Building a proprietary AI context engine
15:03 – How AI is reshaping organizational design
16:34 – Why empathy and relationships remain human advantages
17:24 – The biggest mistakes companies make with AI
18:20 – Why replacing sales reps with AI can burn territories
19:18 – Freeing sales teams to spend more time with buyers
21:14 – Dan’s recommended AI and professional-services resources
23:13 – Why portfolio companies may need an AI innovation advisor
23:42 – How to connect with Dan
Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.
🔗 Connect with Alex Rawlings on LinkedIn https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection www.raw-selection.com
