Coaching Sales Teams: Who Should Coach and How Often

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

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