In this episode, Alex Rawlings speaks with Jamyn Edis, digital transformation expert, former VC-backed CEO, and NYU professor. Jamyn shares actionable insights on using AI, data, and automation to drive performance across private equity firms and their portfolio companies.

From dynamic pricing models and A/B testing to agentic AI and accelerating product cycles, Jamyn explains how to cut through the hype, identify real opportunities, and turn AI into measurable value.

⏱️ Episode Highlights

00:00 – Meet Jamyn Edis
30+ years in consulting (Accenture), corporate (HBO, Take-Two), startups, and teaching at NYU. Focused on the intersection of tech, data, and private equity.

02:23 – Common Mistake in PE
Most firms treat data as plumbing, not strategy. Shift from backward-looking reporting to predictive and prescriptive analytics.

03:48 – AI That Delivers ROI
AI must be embedded into daily operations, not stuck in R&D. Productize, operationalize, and commercialize—or risk irrelevance.

05:15 – How AI Builds on Data
AI is powered by historical data but creates forward-looking insights. Use it to improve pricing, marketing, and operations.

06:42 – Case Study: Take-Two Interactive
Jamyn led data science initiatives to optimize pricing and marketing—replacing gut decisions with data-driven experimentation.

08:08 – AI as PE’s Next Value Driver
AI is the new operating system for PE. After leverage and digital transformation, the next edge is intelligence at scale.

09:31 – Advice to PE Firms
Skeptical? “Get out before the business gets out of you.” Overwhelmed? Start small, build prototypes, and focus on real use cases.

11:04 – Agentic AI in Action
Jamyn shares examples of cutting development cycles, boosting campaign ROI, and improving customer service with AI agents.

13:26 – From Problem to Prototype
Diagnose real pain points, create business and technical requirements, and build targeted AI tools that solve specific problems.

14:50 – AI Won’t Replace Humans, But...
Those who use AI will outperform those who don’t. Jamyn explains Jevons Paradox and why productivity leads to new jobs.

18:46 – How Jamyn Diagnoses Opportunities
Structured discovery process, stakeholder interviews, and clear roadmaps to identify where AI and tech can drive value.

22:10 – Every PE Firm Needs an AI Stack
Soon, AI tools will be as essential as data teams or web developers. Invest now in people, platforms, and processes.

23:06 – The Future is AI + Human Judgment
Firms that embed AI deeply—and pair it with operator judgment—will unlock the next generation of alpha.

24:21 – Jamyn’s Book: The Fifth Horseman
An exploration of how AI mirrors humanity and transforms the way we live and lead. AI is trained by us—and reflects us.

29:07 – What Jamyn Reads & Recommends
Books: The Hard Thing About Hard Things, Understanding Media
Podcasts: Pivot, Ezra Klein
TV: Succession – “Still the best corporate training program ever made.”

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

Guest: Brian Gustason, Operating Partner at Craig Group
Host: Alex Rawlings, Founder of Raw Selection

🔍 Episode Summary:

In this episode, Brian Gustason shares practical insights on building scalable go-to-market (GTM) strategies for lower-middle-market, PE-backed companies. With over 25 years of operating and advisory experience, Brian explains how to move beyond traditional, backward-looking due diligence and implement forward-focused GTM strategies across marketing, sales, and customer success.

He walks through a real-world case study of transforming a $30M founder-led business—covering ICP development, sales process creation, lead qualification, and customer retention. Brian also discusses how marginal gains across key sales metrics (win rates, ACVs, churn) can compound into significant growth and how CEOs, sales leaders, and boards can drive accountability and execution.

⏱️ Timestamps:

00:00 – Brian’s background and role at Craig Group
01:30 – Why traditional due diligence often fails to assess growth
03:00 – Real-world GTM transformation of a founder-led distributor
06:00 – Building ideal customer profiles (ICPs) and prioritising markets
09:00 – Improving lead qualification and using pre-suasion techniques
14:00 – Structuring an effective, trainable sales process
17:30 – Playbooks, documentation, and AI tools to support sales
20:00 – Importance of coaching and ongoing process evolution
23:00 – Growth 2.0: Compounding small improvements across KPIs
27:00 – Who owns GTM? Role of CEO, sales leaders, and the board
29:00 – Brian’s content recommendation: The 80/20 Principle and his LinkedIn series

📚 Resources:

• Craig Group: www.craiggroup.io
• Connect with Brian on LinkedIn: Brian Gustason
• Book Recommendation: The 80/20 Principle by Richard Koch

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

Looking to grow your team? Check out our Hiring Guides

for proven strategies, templates, and best practices to make smarter hires.

🎙️ The Private Equity Podcast – Mark Strauch, Founding Partner & President, Alpine Investors

⏱️ Key Takeaways & Timestamps:

00:00 – Intro
Alex welcomes Mark Strauch to discuss Alpine’s unique leadership-driven approach in private equity.

01:00 – From CEO to PE Leader
Mark shares his journey from operator to co-founding Alpine, now with $20B+ AUM.

02:08 – The Industry’s Problem: Lack of Differentiation
Alpine avoids the “deal shop” model, focusing instead on mission-driven, talent-led investing.

05:24 – Talent as Strategy
Alpine’s core philosophy: talent wins. Their “Unleashing Heroes” mantra puts leadership at the heart of every investment.

06:50 – Add-On Acquisitions at Scale
Over 1,000 deals to date, using each as an opportunity to deploy great talent and drive integration.

08:39 – Alpine’s Internal Playbook
Quarterly OFI (Opportunities for Improvement) projects, one-page strategic plans, and a long-term vision define how Alpine operates like a portfolio company.

10:59 – Lessons from Failure
Fund 1 struggled, prompting a shift to talent-first strategy during the 2008 crisis, guided by executive coach Tom Vacola.

15:00 – Building the CEO Bench
Programs like CEO-in-Residence and CEO-in-Training (CIT) bring in and develop top talent—Alpine is now the top recruiter at elite business schools.

18:31 – Attributes Over Resumes
They hire for grit, humility, and emotional intelligence—qualities highly correlated with CEO success.

20:00 – Real-Time Leadership Development
CITs train on the job with structured learning in both hard and soft skills, plus internal peer-learning pods.

24:00 – What Great CEOs Do
Traits include pace, clarity, resilience, focus, and the ability to inspire and win.

27:37 – Alpine’s Ongoing Constraint: Talent
Even now, talent remains the #1 priority across Alpine and its talent-constrained portfolio sectors.

30:47 – Lessons in Building Alpine
Create a strategy only you can win—play a different game, not the same one better.

32:38 – Operator Empathy = Better Investing
Being a former CEO helps Mark bring realism and focus to underwriting and board roles.

34:05 – Book & Coaching Insights
Recent reads include Boyd, The Bible, and classic philosophy. Coaching tip: great coaches help you unlock your own answers.

39:50 – Connect with Mark
💼 Alpine Investors

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

Looking to grow your team? Check out our Hiring Guides

for proven strategies, templates, and best practices to make smarter hires.