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.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Stephen Messer, co-founder of Collective[i] and LinkShare, shares a bold and timely vision for the future of sales—one that trades CRM inefficiencies, seller churn, and impersonal cadences for AI-powered intelligence, real buyer relationships, and a return to value-based growth.

Stephen unpacks how Collective[i] is building the world’s first economic foundation model for B2B sales—a neural network that learns from billions in live market signals and transforms the way companies forecast, prioritize, and engage. If you’re leading a revenue team, this episode will challenge how you think about data, your CRM, and the very structure of your go-to-market engine.

What You’ll Learn:

• The Real Cost of Today’s Sales Stack: Why CRM-driven workflows have created inefficiency, seller burnout, and buyer distrust.
• How Collective[i] Works: The power of neural networks that learn from shared, anonymized go-to-market activity—while keeping client data private and secure.
• Cruelty in Sales (and How to Fix It): A raw and honest take on how modern sales workflows punish reps and buyers—and how AI can fix it.
• The End of Data Entry: How Collective[i] automates pipeline visibility and eliminates the need for reps to “feed the system.”
• The Rise of Relationship-Centric Growth: Why trust, storytelling, and insight—not spam—will win in the next generation of GTM.

Key Topics:

• What’s wrong with current sales tech (and why it’s unsustainable)
• How Collective[i] trains its neural net to understand real buying behavior
• The shift from CRM-driven sales to AI-first revenue intelligence
• “Lifeguards” and the shadow sellers that make or break deals
• Why buyer relationships have eroded—and how to rebuild them
• The moral case for better GTM design
• Real examples of AI uncovering hidden pipeline risk
• Why average sellers will become exceptional (or obsolete) with AI

Guest Spotlight: Stephen Messer

Stephen is the Co-Founder of Collective[i], a next-gen AI platform reinventing how companies forecast, collaborate, and close. He’s also known for co-founding LinkShare, the affiliate marketing pioneer acquired by Rakuten for $425M. A seasoned entrepreneur and thought leader, Stephen now leads Collective[i] in building the world’s first neural network for B2B sales.

Resources & Mentions:

• Collective[i] – Website
• CI Forecast: Collective[i]’s weekly go-to-market leadership event
• Book mentioned: Predictable Revenue (and its long-term impact on sales culture)
• Topics discussed: AI-powered forecasting, seller efficiency, CRM alternatives, cadence fatigue, relationship rebuilding, data trust models

Listen now and follow Selling the Cloud for more unfiltered GTM insights from the leaders shaping the future of sales.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this Selling the Cloud conversation, Josh Payne dives deeper into the future of AI-first growth teams, and how CoFrame is helping B2B orgs replace legacy handoffs and static workflows with continuously learning, automated systems.

Josh shares how teams are deploying AI to automate experimentation, generate code, and even shape strategy in real time. He outlines what it takes to build with AI in production (not just in prompts), how roles like “growth engineer” are evolving, and why building competitive advantage in 2025 means more than just adding ChatGPT to your stack.

What You’ll Learn:

• How AI Is Reshaping Growth Roles: Why marketers are evolving into orchestrators, engineers, and agents of optimization.
• Beyond Prompting—Toward Infrastructure: How CoFrame builds stable, repeatable workflows with AI that can learn, adapt, and improve continuously.
• Real-World Agent Use Cases: From UI code generation to multivariate testing and funnel orchestration, Josh shares how real AI agents are driving results.
• Why Speed > Strategy (Sometimes): Why fast learning cycles and live tests can outperform static GTM plans.
• How to Start Now: Advice for teams getting started with AI-based systems—without needing a research lab.

Key Topics:

• AI in modern GTM orgs
• Code agents vs. code generation
• Automating testing, design, and targeting
• The rise of “quant growth” as a function
• Breaking down silos with intelligent workflows
• When to trust AI—and when not to
• CoFrame’s real-world implementation stories
• GTM roles of the future: orchestrators vs. operators

Guest Spotlight: Josh Payne

Josh Payne is CEO of CoFrame and a leading voice at the intersection of AI, UX, and growth strategy. A repeat founder and AI researcher, he previously created GPT-Migrate and led growth products at top SaaS and fintech companies. His mission: make the web feel intelligent again.

Resources & Mentions:

• Website: CoFrame
• Concepts: AI agents, orchestration layers, living interfaces, growth stacks
• Tech Stack Mentions: GPT-4, Claude, OpenAI fine-tuning, VWO, Retool

🎧 Listen now and follow Selling the Cloud for more GTM conversations on scaling with AI, orchestrating growth, and building what’s next.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.