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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