In Part 2 of our conversation with Steve Smith, Chief Revenue Officer at Live Oak Fiber, we go deeper into how his team is scaling with both agility and authenticity—blending AI, community engagement, and a customer-first mindset to win in a highly commoditized telecom market.

Steve unpacks what it really means to lead with transparency, build a culture that thrives across residential and B2B markets, and design a sales engine that delivers personalized value at scale. From t-shirt cannons to AI-assisted prospecting, it’s clear: growth happens when you meet your customers where they are—and actually understand who they are.

What You’ll Learn

• Competing Beyond the Product: Why the best way to differentiate is not what you sell—but how you serve.
• Human + AI Prospecting: Steve shares how Live Oak’s team blends digital ads, field outreach, and AI signals to achieve 80%+ MQL conversion.
• Leveraging Customer Context: How insights like home square footage and pool size help personalize campaigns—and why trust starts before the first call.
• Net Promoter as a North Star: The cultural and operational moves that helped Live Oak achieve a 76 NPS score—higher than Apple.
• Culture-Driven Growth: Why hiring “athletes,” not just resumes, is key to building high-performance sales teams in uncertain markets.
• AI Without the Hype: How Steve’s team uses AI practically—from outage alerts to upgrade prompts—without losing the human connection.

Key Topics

• GTM in both residential and business segments
• Creating “shock & awe” customer experiences
• Mapping Day 0 strategies with local event engagement
• Designing growth systems that work across sales channels
• Using CRM, digital behavior, and AI for smarter targeting
• Balancing automation with local, white-glove service
• Operationalizing culture in sales teams and hiring practices

Guest Spotlight: Steve Smith

Steve Smith is the Chief Revenue Officer at Live Oak Fiber, where he leads a people-first, tech-enabled go-to-market strategy across residential, MDU, and commercial segments. With more than 25 years of experience in telecom, Steve is known for his bold talent bets, operational creativity, and unwavering customer obsession.

Resources & Mentions

• Book: Good to Great by Jim Collins
• Book: Blink by Malcolm Gladwell
• Inspiration: The Savannah Bananas
• Sales Concept: “People don’t buy drill bits. They buy holes.”

🎧 Listen now and subscribe to Selling the Cloud 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.

In this episode of Selling the Cloud, Steve Smith, Chief Revenue Officer at Live Oak Fiber, joins co-hosts Mark Petruzzi and KK Anderson to share what it really takes to stand out in a commoditized market. Drawing from 25+ years of telecom and GTM leadership, Steve reveals how Live Oak is building a “fiercely local” go-to-market model powered by customer obsession, simplicity, and a people-first sales culture.

From recruiting talent outside the industry to treating broadband like a luxury retail experience, Steve breaks down how to differentiate when your product looks the same as everyone else’s on paper, and why NPS scores in the 70s are possible when you design everything around the end user.

What You’ll Learn

• How to Compete in a Commodity Market: Why Live Oak avoids tech jargon and positions packages around home square footage—because customers don’t care about speeds, they care about experiences.
• Hiring Outside the Box: Why Steve hires from Louis Vuitton and paddleboard shops, not just telecom resumes—and how that decision drives creativity and customer care.
• Fiercely Local GTM: Learn how a hyperlocal mindset builds trust, unlocks referrals, and builds brand advocacy—especially in overlooked communities.
• Customer Experience that Rivals Apple: How Live Oak’s white-glove service and full-time technicians boost NPS to 76 (compared to cable companies’ scores below zero).
• Product Simplicity That Wins: How pricing transparency and a “price-for-life” model inspired by the Savannah Bananas builds loyalty and eliminates churn frustration.

Key Topics

• Building a customer-first sales culture
• Differentiating when your product is a utility
• Segmenting sales teams by audience (residential, MDU, SMB)
• Why most broadband companies have a bad reputation—and how to flip it
• Local community engagement as a growth strategy
• Metrics that matter: NPS, feedback loops, and service consistency

Guest Spotlight: Steve Smith

Steve Smith is the Chief Revenue Officer at Live Oak Fiber, where he leads go-to-market strategy across residential, business, and MDU channels. A veteran telecom executive with a passion for customer-first innovation, Steve is helping redefine broadband with a culture that starts and ends with people—both inside and outside the business.

Resources & Mentions

• Book: Good to Great by Jim Collins
• Book: Start with Why by Simon Sinek
• Inspiration: Savannah Bananas (yes, really!)

🎧 Listen now and subscribe to Selling the Cloud wherever you get your podcasts. Stay tuned for Part 2 with Steve next week!

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 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.

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.

In this episode of Selling the Cloud, Josh Payne—Founder & CEO of CoFrame and creator of GPT-Migrate—joins Mark Petruzzi and KK Anderson to explore how AI agents and continuously optimizing websites are changing the future of digital growth.

Josh shares how CoFrame is helping mid-market and enterprise companies drive 30%+ increases in conversion by building adaptive, AI-powered interfaces that test, learn, and optimize in real time. He also unpacks how his team partnered with OpenAI to create a state-of-the-art UI code generation model—and what this signals about the future of growth marketing.

Whether you’re a CMO, growth lead, or founder looking to build durable competitive advantage through AI, this episode will shift your mindset and your roadmap.

What You’ll Learn:

• From Static to Living Interfaces: Why websites are broken—and how AI agents can continuously optimize them based on real-time data and buyer behavior.
• The End of Manual A/B Testing: How Josh’s team automates experimentation at scale to unlock compound conversion lifts without traditional resource bottlenecks.
• Inside the OpenAI Partnership: How CoFrame trained a UI-specific code generation model that understands brand, layout, and style—then deployed it at scale.
• Building Competitive Advantage with AI: Why businesses that embrace continuous optimization today will outpace those stuck in manual, quarterly workflows.
• Designing the Future Growth Stack: How AI agents, data orchestration, and strategy automation will transform marketing roles and unlock new GTM velocity.

Key Topics:

• Living interfaces vs. static websites
• AI code generation for brand-consistent design
• Scaling experimentation with AI agents
• The future of CRO: conversion rate optimization
• AI in paid media, lifecycle marketing, and SEO
• Strategy design vs. manual execution
• How to evaluate AI models like Claude, Gemini, GPT-4
• Building “quant growth” systems for marketing
• Why the next big AI use case is growth engineering

Guest Spotlight: Josh Payne

Josh is the CEO of CoFrame and a repeat founder with deep roots in AI. He previously co-founded Autograph (a $2B+ unicorn), created GPT-Migrate, and authored over 20 patents and AI research papers. At CoFrame, he’s pioneering AI-first digital experiences that adapt to users in real time.

Resources & Mentions:

• CoFrame: https://coframe.com
• Article: The New Science of Growth Marketing – Every
• Tech: GPT-4 Vision, Claude, MoonDream, OpenAI fine-tuning
• Tools Mentioned: Optimizely, Adobe Target, VWO, Amplitude
• Topic: Quant growth, UI code generation, AI agents

🎧 Listen now and follow Selling the Cloud for cutting-edge conversations with the builders, strategists, and GTM leaders shaping the future of sales, growth, and AI.

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, Mike Milburn—former Chief Customer Officer at Salesforce and founding team member of Service Cloud—joins Mark Petruzzi and KK Anderson for a masterclass in aligning product and sales teams around a shared go-to-market mission.

Drawing from his 15+ years at Salesforce, Mike shares hard-won frameworks for building product roadmaps that sales can actually sell, developing trust between CROs and CPOs, and scaling alignment across growth stages. This is a blueprint for leaders who want revenue-generating product strategy—not just internal harmony.

What You’ll Learn:

• The Product–Sales Friction Point: How most teams mismanage this relationship and how to turn it into a revenue advantage.
• Revenue-Calorie Framework: Why Salesforce prioritized roadmap decisions by “calories” and how to balance innovation vs. renewals.
• V2MOM as a GTM Operating System: What the V2MOM framework taught Mike about prioritization, transparency, and shared accountability.
• From Anecdotes to Data: How to structure sales feedback into decision-ready inputs for product teams.
• Product + Sales = One Team: What world-class collaboration looks like—when sales leaders evangelize the roadmap and product leaders join customer conversations.

Key Topics:

• CRO and CPO relationship-building strategies
• Translating sales objections into roadmap investment
• The role of customer success in roadmap prioritization
• Quantifying “deal blockers” to influence product
• Running effective board conversations around product
• How “True to the Core” made Salesforce a customer-led company
• Scaling product-sales collaboration from startup to enterprise

Guest Spotlight: Mike Milburn

Mike Milburn is the former Chief Customer Officer at Salesforce and was part of the founding team of Service Cloud. Today, he serves as an advisor to multiple SaaS companies. His career centers on building GTM systems where product, sales, and customer success function as one growth engine.

Resources & Mentions:

• Framework: V2MOM – Vision, Values, Methods, Obstacles, Metrics
• Salesforce Event: “True to the Core” session at Dreamforce
• Recommended Book: Behind the Cloud by Marc Benioff
• Other Concepts: Revenue-calorie model, sales telemetry, deal blocker mapping

🎧 Listen now and follow Selling the Cloud for more insights from GTM leaders building high-growth, cross-functional teams. 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.