From Playbooks to Performance: How John Head Bridges the Sales Execution Gap

Overview

In this episode of The Gap, Coach K interviews John Head, the Chief Revenue Officer (CRO) of Aetos Imaging, to explore one of the biggest challenges in sales: bridging the gap between theoretical playbooks and real-world execution.

John shares his journey from consulting to leading revenue teams, his approach to building actionable sales playbooks, and his strategies for coaching sales teams to success. He also discusses how technology, AI, and collaboration play a vital role in enabling sales teams to perform at their best. Whether you’re a CRO, sales leader, or part of an enablement team, this episode offers practical tips and actionable insights.

Takeaways

• Coaching as the Cornerstone of Sales Success: Effective coaching bridges the gap between theory and execution. John highlights the importance of observing key moments in sales interactions, documenting them, and providing constructive feedback to help reps refine their approach.

"Without a doubt, coaching is the primary method... Capturing that moment and cataloging it is key to improvement."

He emphasizes that coaching isn’t about fixing mistakes—it’s about empowering reps to internalize skills they can rely on in the field.

• Playbooks Should Be Practical and Dynamic: John explains that a playbook isn’t just a document—it’s a living, practical guide. A well-crafted playbook focuses on actionable content, such as how to handle objections, position solutions, and establish value, all tied to different stages of the revenue cycle.

"Playbooks are not a marketing thing—they are pragmatic content that we’ve developed and used in multiple situations that we know works."

Keeping playbooks updated ensures that the team is equipped to handle evolving market challenges.

• AI and Technology Are Transforming Sales Enablement: John sees immense potential in AI for capturing critical moments in sales calls and providing real-time enablement. He envisions AI tools becoming essential for equipping sales teams with contextually relevant knowledge.

"The real magic happens in those moments... You’ve got to take advantage of them with the right tools."

At Aetos, he’s exploring how AI can streamline knowledge capture and help reps improve their performance at scale.

• Enablement is a Continuous Process: John dedicates bi-weekly enablement sessions to skill-building and practice. These sessions focus on modeling best practices and giving reps a chance to rehearse in a supportive environment.

"I spend a lot of time teaching them to internalize it so they really make it their own... I’m going to show you how it’s done."

This structured approach ensures reps know what good looks like and feel confident applying those skills.

• Collaboration is Key Across the Revenue Cycle: John’s “two-headed monster” approach ensures collaboration at every stage of the sales process. AEs work closely with BDRs, solution consultants, and customer success managers to ensure seamless handoffs and a unified customer experience.

"The AE is the constant, but others come in and out based on where the account is in
its maturation."

This approach keeps the team aligned and ensures no opportunities are lost due to communication gaps.

• Tailored Coaching for Individual Strengths: John believes in understanding each team member’s unique strengths and addressing their specific gaps. His coaching is tailored to help each rep excel while maintaining consistency in
team performance.

"I’m constantly assessing what gaps my folks have and how I can mitigate those gaps in the best way possible."

This approach balances team standards with individual growth.

• Capturing and Scaling Knowledge: John emphasizes the importance of systematically capturing learnings and sharing them across the team. This ensures that everyone benefits from insights gained in the field.

"How do we consistently capture this and use it as a continuum? That’s the eye
on the prize."

Scalable knowledge capture allows the team to adapt and improve over time.

TL;DR

• Coaching is crucial for translating playbooks into action.
• Practical playbooks evolve with market changes and team needs.
• AI tools enable real-time sales support and faster improvement.
• Bi-weekly enablement sessions build skills through practice and modeling.
• Cross-functional collaboration ensures seamless execution across the revenue cycle.
• Personalized coaching maximizes individual strengths and addresses gaps.
• Knowledge capture systems help scale insights across the team.