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 stay ahead. He also shares how Disqo is rethinking GTM structure and leveraging AI to drive personalization, speed, and operational clarity; without drowning in tools.

What You’ll Learn

• Why the Playbook is Obsolete: What Neil really means when he says the old models no longer work, and what replaces them.
• Lightweight Rigor at Scale: How to build process and alignment without slowing teams down.
• From Bottoms-Up to Top-Down TAM: How Disqo blends relationship selling with TAM-led targeting for scale.
• Curiosity as Culture: Why curiosity is a non-negotiable leadership trait in flat, fast-moving GTM orgs.
• Leading Through Change: How to coach teams to self-govern, move fast, and stay mission-aligned in a no-layer org model.

Key Topics

• Building sales organizations without bureaucracy or bloat
• Aligning marketing, sales, and success teams around business outcomes
• Using AI to power real-time customer insight and hyper-relevant outbound
• Flattening GTM structures for speed, ownership, and clarity
• Creating cultures where experimentation and impact are rewarded

Guest Spotlight: Neil Graham

Neil Graham is the Chief Revenue Officer at Disqo and a proven sales leader with decades of experience scaling GTM organizations from Series A to post-IPO. Known for his ability to bring structure without red tape, Neil has helped some of the most recognized B2B SaaS names balance scale with agility in high-growth phases.

Resources & Mentions

• Company: Disqo
• Framework: DSF (Disqo Success Framework)
• Sales Tools: Gong, Clay, ChatGPT
• Books & Influence: MedPick methodology, Salesforce early days, AI-led sales enablement

🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.

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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 readiness.

What You’ll Learn:

• Leading Through Change: How to stabilize culture and focus teams during M&A, leadership transitions, or high-stakes GTM shifts
• Mutual Action Plans that Work: Why aligning around a co-created calendar is a simple but powerful tool for accountability and momentum
• Consistency Over Chaos: How sticking to your core value proposition helps drown out internal and external noise
• Real AI Use Cases: How Josh and his team use AI for onboarding, writing, analysis, and market research—without replacing human judgment
• Leadership in Modern Sales Orgs: The behavioral traits that inspire performance, loyalty, and resilience

Key Topics:

• Sales leadership in high-pressure, transitional environments
• Using backward-planning and mutual calendars for deal velocity
• Staying aligned on value across long sales cycles
• Cultural consistency across internal and client-facing teams
• AI for productivity, market intelligence, and GTM strategy
• Embracing humility and continuous learning as a CRO

Guest Spotlight: Josh Hoffman

Josh is Chief Revenue Officer at Totus Rx and a long-time leader in B2B revenue organizations. He’s built and led sales teams across tech, telecom, and compliance industries, with a focus on building high-trust teams and delivering real value to customers. Josh is known for his practical, human-centered leadership style, especially in complex, high-stakes environments.

Resources & Mentions:

• Book: The Challenger Sale
• Book: SPIN Selling
• Leaders Mentioned: Mark Anderson, Russ Reeder, Todd Abbott, Mike Jenner, Joe Burton
• Follow Josh Hoffman on LinkedIn for more insights on sales leadership and culture.

🎧 Listen now and subscribe to Selling the Cloud to hear more from enterprise GTM leaders shaping the future of sales.

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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, humility, and emotional intelligence in modern sales leadership. From shifting away from zero-sum thinking to building customer-aligned mutual action plans, this episode is a masterclass in outcome-based selling and team-driven success.

What You’ll Learn

• Sell-With vs. Sell-To: Why Josh believes the most successful sellers don’t “close deals”, they solve problems alongside the customer.
• How to Build Mutual Action Plans: Practical ways to bring partners and clients to the same side of the table from day one.
• The Role of AI in Sales Coaching: How Josh’s teams are using AI for prompt writing, context synthesis, and deal prep, without losing the human element.
• Coaching Through Change: Why consistency, not charisma, helps teams thrive through high-pressure acquisitions and pivots.
• From Manufacturing to CRO: Josh’s story of going from putting screws in motherboards at Dell to building global GTM teams, and what shaped him along the way.

Key Topics

• Transforming sales cultures from transactional to consultative
• Teaching sellers to ask better questions, and when to talk less
• Why top sales leaders reduce the distance between themselves and the AE
• Coaching through ambiguity and building career-defining moments
• Why consistent behavior builds trust in times of change
• Using AI to augment, not replace, frontline coaching and prep

Guest Spotlight: Josh Hoffman

Josh Hoffman is the Chief Revenue Officer at ControlCase and a proven sales leader with over two decades of experience building high-performance teams. With a track record of leading in moments of transformation, Josh is passionate about coaching sellers to exceed what they thought was possible, through shared success, customer obsession, and scalable systems of growth.

Resources & Mentions

• Book: The Qualified Sales Leader by John McMahon
• Book: FYI: For Your Improvement by Korn Ferry
• Company: ControlCase (compliance & audit automation)
• AI Tool Mention: Grammarly, prompt engineering
• Leadership Inspiration: Todd Abbott, Mike Jenner, Mark Anderson

🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.

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In Part 2 of our conversation with Max Elster, Co-Founder and CEO of Minoa, we go deeper into how sales teams are actually operationalizing outcome-based selling; at scale.

Max shares how revenue teams at companies like Vanta are moving beyond founder-led, feature-centric narratives, and building scalable, repeatable playbooks rooted in customer outcomes, business impact, and data-backed storytelling.

Whether you’re leading a 10-person sales team or a 1,000-person GTM org, this conversation will help you reimagine enablement, coach for value, and build business cases that win over CFOs.

What You’ll Learn

• Vanta’s Transition from Features to Outcomes: How CRO Stevie Case transformed Vanta’s narrative, and drove shorter cycles, higher win rates, and stronger executive engagement by focusing the team on value-led discovery and storytelling.
• Why Business Cases Shouldn’t Be Optional: Hear how teams went from building 10 business cases per quarter to over 500, without hiring hundreds of SEs, and how that shift boosted win rates by up to 15 percentage points.
• Teaching Reps to Think Like CFOs: Max explains how the best sales teams equip champions to model ROI and outcomes with buyers, not for them, and why the strongest business cases are co-owned with the finance team.
• How AI Accelerates Discovery, Coaching, and Differentiation: From call summaries to intent signals to customer benchmarks, Max shows how LLMs and predictive tools are giving reps the context to build relevance at scale, without losing the human touch.

Key Topics

• From founder-led sales to repeatable revenue engines
• Vanta’s shift to value-led selling, and what it unlocked
• Building outcome plans that close deals faster
• Why the CRO’s best insights come from AEs
• Coaching for customer outcomes, not product demos
• How AI is reshaping forecasting, discovery, and enablement
• The real future of revenue leadership in an AI world

Guest Spotlight: Max Elster

Max Elster is the Co-Founder and CEO of Minoa, a revenue platform helping companies scale value-based sales across the deal cycle. With a decade of experience in AI and B2B SaaS, Max works with companies like Vanta, Cognite, and others to operationalize value intelligence, from discovery to renewal.

Resources & Mentions

• Book: The Qualified Sales Leader by John McMahon
• Company: Vanta
• Max Elster: LinkedIn | Email: max@minoa.io

🎧 Listen now and subscribe to Selling the Cloud wherever you get your podcasts. Stay tuned for next week’s episode!

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In this episode of Selling the Cloud, Max Elster, Co-Founder and CEO of Minoa, joins co-hosts Mark Petruzzi and KK Anderson to explore what B2B revenue leaders often miss: a clear, consistent understanding of why they win.

Max introduces the concept of a Value Intelligence Layer, a data-driven framework that links discovery, business cases, and outcomes into a single narrative that everyone from SDRs to CROs can use.

Drawing from years of experience across SaaS and enterprise sales, Max shares how leading GTM teams are moving away from feature pitching and toward outcome-led selling, especially in a world where AI has made building software easier, and differentiation harder.

From strengthening discovery questions to creating scalable outcome playbooks, this episode is packed with tactical ideas for revenue leaders rethinking how they sell in the age of AI.

What You’ll Learn

• The “Why We Win” Blindspot: Why many sales orgs still can’t answer the most important question, and how that gap leads to poor qualification, forecasting, and deal execution.
• From Features to Outcomes: How modern buyers evaluate value, and why understanding customer priorities matters more than your internal product roadmap.
• Creating the Value Intelligence Layer: How to unify customer impact, product usage, sales stages, and discovery insights into a single GTM operating model.
• Scaling Outcome-Led Playbooks: What it takes to align SDRs, AEs, SEs, and CS teams around a shared value narrative from day zero to renewal.
• AI as a Differentiator (Not a Replacement): Why the best teams use AI to personalize engagement, not to automate it, and how AI helps surface deeper buyer context.

Key Topics

• Why most GTM teams don’t know why they win
• Building discovery questions that lead to business cases
• Embedding outcomes into CRM and sales stages
• Creating a “value intelligence” system across teams
• How AI and call data can power more relevant sales motions
• Turning post-sale value into pre-sale advantage
• Aligning playbooks across SDRs, AEs, SEs, and CSMs

Guest Spotlight: Max Elster

Max Elster is the Co-Founder and CEO of Minoa, a SaaS company helping revenue teams operationalize their value story. With a background in B2B software and product development, Max built Manoa to bridge the gap between feature-led selling and outcome-driven growth. His team helps sales orgs unify discovery, use cases, and customer impact into one connected system.

Resources & Mentions

• Book: The Qualified Sales Leader by John McMahon
• Company: Minoa.io
• Max’s LinkedIn: linkedin.com/in/maxelster

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

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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.

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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!

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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.

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