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Ep. 92 – Building Tech-Enabled Revenue Teams with Jamie Wilkinson – Part 2
In Part 2 of this Selling the Cloud episode, Jamie Wilkinson, CEO of Smart4Cloud.ai, continues his insightful conversation with Mark Petruzzi and KK Anderson on how today’s revenue teams must evolve beyond job specs and tech stacks.
From building integrated, cross-functional orgs to navigating partner ecosystems, Jamie breaks down how human-centered leadership and honest business assessment unlock true scalability. He also shares the key attributes that define top sales leaders and how to spot high-impact talent in any market.
What You’ll Learn:
- Cross-Functional Alignment is a Growth Lever: Why modern revenue teams can’t operate in silos and how top-performing orgs build “fluidity” between sales, finance, tech, and marketing.
- Humanizing the Hiring Process: How Jamie’s commitment model goes beyond résumés to find high-performing candidates who align with the company’s story—not just the bullet points.
- AI Isn’t the Enemy or the Answer: Jamie shares a grounded take on AI: it’s not about fear or hype, but about how humans apply it to improve real lives and sales performance.
- Build or Buy? Market Expansion Strategy: Jamie discusses when to build internally vs. leverage partner ecosystems, and why brutal honesty is the real unlock for scale.
- Agility, Honesty, and Culture: The traits Jamie believes will define successful GTM teams over the next 12–18 months.
Key Topics:
- Aligning technical, sales, and product leadership
- How to recruit talent that thrives in integrated orgs
- Getting past fear-based narratives around AI
- Internal vs. external capability building
- Leadership traits that matter in “normal” markets
- How to spot people with “G.A.S.” (Givers who actually… care)
Guest Spotlight: Jamie Wilkinson
Jamie Wilkinson is the Founder and CEO of Smart4Cloud.ai, a human-first revenue talent partner for modern B2B teams. With deep experience in building technical + sales hybrid teams, Jamie brings practical wisdom and a no-BS approach to growing revenue orgs that work.
Resources & Mentions:
- Part 1 of Jamie Wilkinson’s episode
- Guest Mention: Napoleon Baligan, founder of 1-800-Mattress
- Reference Book: To Sell is Human (by implication)
- Podcast: Selling the Cloud
🎧 Listen now and follow Selling the Cloud for more GTM insights from leaders who’ve done the work. Subscribe wherever you get your podcasts.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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By Mark Petruzzi, KK Anderson, Paul Melchiorre
4.4
88 ratings
In Part 2 of this Selling the Cloud episode, Jamie Wilkinson, CEO of Smart4Cloud.ai, continues his insightful conversation with Mark Petruzzi and KK Anderson on how today’s revenue teams must evolve beyond job specs and tech stacks.
From building integrated, cross-functional orgs to navigating partner ecosystems, Jamie breaks down how human-centered leadership and honest business assessment unlock true scalability. He also shares the key attributes that define top sales leaders and how to spot high-impact talent in any market.
What You’ll Learn:
- Cross-Functional Alignment is a Growth Lever: Why modern revenue teams can’t operate in silos and how top-performing orgs build “fluidity” between sales, finance, tech, and marketing.
- Humanizing the Hiring Process: How Jamie’s commitment model goes beyond résumés to find high-performing candidates who align with the company’s story—not just the bullet points.
- AI Isn’t the Enemy or the Answer: Jamie shares a grounded take on AI: it’s not about fear or hype, but about how humans apply it to improve real lives and sales performance.
- Build or Buy? Market Expansion Strategy: Jamie discusses when to build internally vs. leverage partner ecosystems, and why brutal honesty is the real unlock for scale.
- Agility, Honesty, and Culture: The traits Jamie believes will define successful GTM teams over the next 12–18 months.
Key Topics:
- Aligning technical, sales, and product leadership
- How to recruit talent that thrives in integrated orgs
- Getting past fear-based narratives around AI
- Internal vs. external capability building
- Leadership traits that matter in “normal” markets
- How to spot people with “G.A.S.” (Givers who actually… care)
Guest Spotlight: Jamie Wilkinson
Jamie Wilkinson is the Founder and CEO of Smart4Cloud.ai, a human-first revenue talent partner for modern B2B teams. With deep experience in building technical + sales hybrid teams, Jamie brings practical wisdom and a no-BS approach to growing revenue orgs that work.
Resources & Mentions:
- Part 1 of Jamie Wilkinson’s episode
- Guest Mention: Napoleon Baligan, founder of 1-800-Mattress
- Reference Book: To Sell is Human (by implication)
- Podcast: Selling the Cloud
🎧 Listen now and follow Selling the Cloud for more GTM insights from leaders who’ve done the work. Subscribe wherever you get your podcasts.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.