In this episode of Selling the Cloud, Jamie Wilkinson, CEO of Smart4Cloud.ai, joins Mark Petruzzi and KK Anderson to explore how the best revenue organizations combine technical talent and sales leadership to create scalable, high-impact GTM engines.
With 25 years of experience in both technical talent strategy and revenue organization design, Jamie breaks down how CROs and CEOs can avoid siloed growth models by integrating sales and technical infrastructure, especially in today’s AI-powered ecosystem.
What You’ll Learn:
- Tech Talent as Revenue Infrastructure: Why roles like solution architects, SEs, and customer-facing engineers are now critical for sales success, not just delivery.
- Overcoming Tool Sprawl: How to focus less on “more tools” and more on extracting real value from your existing stack.
- Culture > Tech: Why a strong leadership culture still outperforms even the best tech when it comes to execution.
- The Visibility Gap: How AI platforms like Collective[i] help sales orgs see what’s really happening so they can coach, forecast, and prioritize smarter.
- How to Hire for AI-Era Sales: What today’s technical-hybrid sales roles look like, and how to recruit for adaptability, not just hard skills.
Key Topics:
- Sales leadership architecture
- Customer-facing technical roles in modern GTM
- Strategic use of AI tools in sales orgs
- Aligning technical capabilities with deal velocity
- Why forecasting is broken—and how to fix it
- The difference between productivity KPIs vs. outcome KPIs
- Revenue visibility and operational clarity
- Leadership lessons from elite team sports
Guest Spotlight: Jamie Wilkinson
Jamie Wilkinson is the founder and CEO of Smart4Cloud.ai, where he helps revenue leaders architect both technical and sales teams to drive market advantage. With a background in elite sales recruiting, technical hiring, and growth strategy, Jamie brings a unique lens to what it takes to scale high-performance organizations in the AI era.
🎧 Listen now and follow Selling the Cloud for practical GTM strategies and sharp conversations at the edge of sales, leadership, and growth.
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