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PODCAST

Selling the Cloud

Mark Petruzzi, KK Anderson, Paul Melchiorre

Selling the Cloud delves into the stories of C-suite veterans in Sales, Marketing, Customer Success, and RevOps, revealing the secrets behind building successful SaaS empires. Each episode features seasoned leaders who walk through their career journeys, sharing the wins and lessons learned along the way. From mastering customer acquisition to leveraging AI-powered marketing and sales strategies, our guests provide actionable insights for driving growth and business success in the B2B SaaS

business management

All Episodes

00:26:43

Ep. 116 – Escaping the Crisis of Sameness in Modern...

Selling the Cloud ·

2026/03/03

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Doug Landis, Co-Founder of StoryPath.ai and host of Sales Stories, to unpack how AI is reshaping the buyer seller relationship and why most sales teams are still playing by outdated rules.Doug shares why AI has enhanced the buyer’s world more than the seller’s, what he calls the invisible evaluation, and how today’s buyers are 80 to 90 percent through their decision process before ever speaking to a rep. The

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00:21:35

Ep. 115 - Building Repeatable Sales Success in...

Selling the Cloud ·

2026/02/24

In Part 2 of this conversation on Selling the Cloud, Glenn Poulos dives deep into what it really takes to scale a distribution business from startup to successful exit. From growing Gap Wireless from 1 million dollars in revenue to 84 million over 15 years, Glenn shares the strategic decisions, mindset shifts, and leadership disciplines that enabled sustainable growth in the telecom technology sector.Glenn unpacks the importance of franchise vendor relationships, why brand positioning determines

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00:25:02

Ep. 114 - Building Repeatable Sales Success in...

Selling the Cloud ·

2026/02/17

In this episode of Selling the Cloud, Glenn Poulos joins Mark and KK Anderson to break down what truly drives success in complex enterprise B2B sales. With over 40 years of experience selling technical solutions across telecom, wireless infrastructure, and power utilities, Glenn shares the practical frameworks behind building trust, mapping decision processes, and creating repeatable sales performance.Drawing from his book Never Sit in the Lobby and decades of hands-on leadership, Glenn explains

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00:22:27

Ep. 113 – From CRO to CEO: What Boards Really Look...

Selling the Cloud ·

2026/02/10

In Part 2 of this Selling the Cloud conversation, Mark Petruzzi and KK Anderson continue their discussion with Jason Baumgarten, diving deeper into how boards think, govern, and evaluate senior sales leaders once they reach the highest levels of leadership.Jason unpacks why boards care less about confidence and more about clarity, learning, and diagnosis. He explains how CROs must evolve from operators into enterprise leaders who understand risk, governance, succession planning, and investor

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00:24:38

Ep. 112 – From CRO to CEO: What Boards Really Look...

Selling the Cloud ·

2026/02/03

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson are joined by Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stuart, to unpack what truly separates sales leaders who advance into CEO and board roles from those who remain stuck at the functional level.Drawing from more than 250 CEO and board transitions, Jason shares a rare behind-the-scenes perspective on how boards evaluate CROs, why ambition alone is not enough, and what sales leaders must change as

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00:13:27

Ep. 111 – Building AI Fluency, Trust, and Modern...

Selling the Cloud ·

2026/01/27

In Part 2 of this Selling the Cloud conversation, Cherilynn Castleman joins Mark and KK Anderson to unpack what strong CRO leadership looks like in a time of rapid AI adoption and constant go-to-market change. As every team claims to be AI-first and tech stacks continue to converge, Cherilynn explains what truly differentiates leaders who drive real results.This episode dives into how curiosity with AI, disciplined daily usage, and protecting selling time translate into cleaner pipelines, shorter

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00:25:36

Ep. 110 – Building AI Fluency, Trust, and Modern...

Selling the Cloud ·

2026/01/20

In this episode of Selling the Cloud, Cherilynn Castleman, enterprise sales leader turned strategic coach and Harvard instructor, joins Mark Petruzzi and KK Anderson to break down what AI fluency really means for modern sales teams. Rather than treating AI as a shortcut or replacement, Cherilynn reframes it as an amplifier of human strengths like perspective, empathy, and trust. She shares practical, Monday-ready routines that help sellers show up with stronger points of view, deeper buyer

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00:17:30

Ep. 109 - Scaling the Right Way: Product Market Fit,...

Selling the Cloud ·

2026/01/13

In Part 2 of this Selling the Cloud conversation, Mark Roberge joins KK Anderson and Mark Petruzzi to go deeper into what happens after product market fit is achieved and why going too fast too early can quietly break a business.Mark breaks down the transition from product market fit to go to market fit, explaining why these stages must be earned in sequence, not pursued in parallel. He outlines what real go to market readiness looks like, how to design a buyer centric sales system, and why

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00:19:30

Ep. 108 - Scaling the Right Way: Product Market Fit,...

Selling the Cloud ·

2026/01/06

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Mark Roberge, founding CRO at HubSpot and author of The Sales Acceleration Formula, to unpack why most companies scale at the wrong time and with the wrong signals. Mark introduces a stage-specific, data-driven framework for moving from product market fit to go to market fit, and explains why managing to readiness and retention beats chasing top-line revenue alone. Mark breaks down how founders and boards get trapped

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00:13:45

Ep. 107 - Building Revenue Teams That Thrive in the...

Selling the Cloud ·

2025/12/28

In Part 2 of this Selling the Cloud conversation, Amy Weber joins KK Anderson and Mark Petruzzi to go deeper into how modern revenue leaders should think about AI, outreach, hiring, and coaching. Amy challenges traditional sales motions like cold outreach and rigid playbooks, and explains how AI should be used to personalize engagement, free up seller time, and enable more meaningful one on one conversations.The discussion also dives into assessment driven hiring and coaching, unpacking why

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00:22:01

Ep. 106 - Building Revenue Teams That Thrive in the...

Selling the Cloud ·

2025/12/16

In this episode of Selling the Cloud, Mark and KK sit down with Amy Weber, founder of Vetta Sales Consulting and strategic advisor to GrowthStage and Enterprise revenue teams. Amy specializes in aligning people, process, and purpose so strategy translates into real performance. She shares why many revenue organizations stall not because of tools or plans, but because of role confusion, misaligned talent, and leadership gaps.Amy breaks down how to design roles that reflect reality, how to hire and

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00:19:14

Ep. 105 - Turning Personal Networks Into Pipeline:...

Selling the Cloud ·

2025/12/07

In this episode of Selling the Cloud, Drew Sechrist, CEO and co-founder of Connect the Dots and longtime Salesforce veteran, joins Mark Petruzzi and KK Anderson to unpack what it really means to build a relationship intelligence layer that changes how your team goes to market.Drew shares why his own career win stories at Salesforce led him to build Connect the Dots, and how mapping real relationship strength can turn stalled enterprise deals into closed revenue. He breaks down the nuance of

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00:23:23

Ep. 104 - Turning Personal Networks Into Pipeline:...

Selling the Cloud ·

2025/11/30

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Drew Sechrist, CEO and co founder of Connect The Dots and longtime Salesforce veteran, to unpack why traditional ABM motions and high volume outbound are running out of gas and what comes next. Drew shares how relationship intelligence, warm introductions, and network aware playbooks are giving revenue teams a durable performance edge over cold, volume driven tactics.Drawing from his experience leading enterprise

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00:21:03

Ep. 103 - Operationalizing Process and AI for Real...

Selling the Cloud ·

2025/11/25

In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrain, joins KK Anderson and Mark Petruzzi for a compelling conversation on how modern sales leaders can use AI to coach more effectively, eliminate wasteful pipeline rituals, and build real self-leadership within their teams.Paul outlines how high-performing sales managers are shifting from performative metrics to meaningful enablement; using AI to flag risk, generate insights, and equip reps to close complex deals. He

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00:22:52

Ep. 102 - Operationalizing Process and AI for Real...

Selling the Cloud ·

2025/11/18

In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrane, joins KK Anderson and Mark Petruzzi to reframe how revenue teams win in complex, multi-stakeholder deals. Paul explains why many orgs over index on apps and one-off skills while under investing in operating rhythms, leadership habits, and relationship-driven execution. He introduces the idea of real intelligence as the who and why that guide the how, and shows how process plus AI inside the workflow can coach

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00:59:24

Ep. 101 – Unlocking AI’s Potential: Mastering the Art...

Selling the Cloud ·

2025/11/11

In this replay of Mastering Sales with AI, AGS Co-Founder Mark Petruzzi is joined by KK Anderson and Scott Stollwerk, Chief Sales Officer at Pest Share, together with Gabriella Koenig of Collective[i], for a lively and practical discussion on how AI is reshaping the art of selling.The conversation dives deep into what separates average sales teams from AI-empowered ones—and it’s not the tech itself. It’s the thinking. The panel explores how smarter questions, better hypotheses, and trust-driven

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00:22:34

Ep. 100 – Leading and Scaling Revenue Organizations...

Selling the Cloud ·

2025/11/04

In Part 2 of our conversation with Neil Graham, Chief Revenue Officer at Disqo, we dive deeper into how modern CROs must rethink their org design, marketing execution, and AI integration strategies to stay competitive in 2025 and beyond. Neil shares why curiosity, humility, and bias for action are now non-negotiables; and how his team is operationalizing those values inside a flat, fast-moving GTM system. From building AI-generated deal strategy sessions to deploying 24/7 agents on the website,

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00:19:14

Ep. 99 – Leading and Scaling Revenue Organizations...

Selling the Cloud ·

2025/10/28

In this episode of Selling the Cloud, we’re joined by Neil Graham, Chief Revenue Officer at Disqo and a seasoned revenue leader whose career spans Salesforce, Siebel, Jive, and Telem. Neil shares a ground-level view of what it takes to lead, scale, and modernize revenue organizations in an era where traditional sales playbooks are no longer enough.From breaking out of funnel-stage rigidity to building flat organizations that prioritize curiosity, Neil walks through the changes CROs must embrace to

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00:20:24

Ep. 98 – Driving Symbiotic Outcomes in High-Stakes...

Selling the Cloud ·

2025/10/21

In Part 2 of our conversation with Josh Hoffman, we explore the leadership mindset required to thrive in moments of high-pressure change, like mergers, long enterprise cycles, and AI-driven disruption.Josh shares how sales teams can stay grounded in customer value, build trust through co-created plans, and lead with consistency; regardless of who owns the company or what the logo says. We also talk about the real-world impact of AI on sales effectiveness, onboarding, and go-to-market

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00:22:21

Ep. 97 – Driving Symbiotic Outcomes in High-Stakes...

Selling the Cloud ·

2025/10/14

In this episode of Selling the Cloud, we sit down with Josh Hoffman, a seasoned go-to-market leader who has guided sales transformations at Dell, Avaya, Poly, Datto, and now ControlCase. Known for his “sell-with” philosophy, Josh shares what it really means to drive symbiotic outcomes, where sellers, partners, and customers win together.He unpacks lessons from decades of leading in high-stakes environments, including mergers, market pivots, and rapid scale, and makes the case for consistency,

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116 results

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