In this episode of Selling the Cloud, hosts Mark Petruzzi and KK Anderson sit down with Ioanna Onasi, CEO of Dextego, to explore the intersection of AI and sales performance. As a leader in AI-driven coaching, Ioanna shares how AI enhances—not replaces—human connection in sales.

Key Topics Covered:

• How AI is revolutionizing soft skills in sales—active listening, empathy, and time management.
• The role of AI in go-to-market execution: real-time coaching, buyer intent signals, and competitive intelligence.
• Future trends in AI-powered sales: VR role-playing, wearable AI, and automated deal rooms.
• Ethical considerations in AI-driven selling: balancing automation with authentic relationships.

Key Takeaways:

• AI is a sales enabler, not a replacement for human interaction.
• AI helps sales teams refine soft skills and optimize outreach timing.
• AI-driven coaching empowers sales reps to shorten cycles and improve conversions.
• The future of AI in sales includes immersive training, predictive analytics, and automation without losing the human touch.

Resources & Links:

• Learn more about Dextego: Dextego.com
• Connect with Ioanna Onasi on LinkedIn
• Follow Selling the Cloud for more insights on AI and B2B sales!

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, hosts Mark Petruzzi and Kathy Minter sit down with Frank Cespedes, a senior lecturer at Harvard Business School and author of Aligning Strategy and Sales. Frank shares his deep expertise on the intersection of business strategy and sales execution, shedding light on why so many organizations struggle to connect their go-to-market plans with real-world sales effectiveness.

The conversation dives into:

The most common strategic missteps companies make and how to fix them.

Why sales leaders must be agents of business strategy, not just revenue drivers.

The impact of misaligned planning processes and market realities.

How sales hiring, training, and performance management should evolve.

Why financial literacy is a must-have skill for today’s CROs.

The rise of AI and data-driven decision-making in sales.

Frank also shares fascinating insights on why business schools have historically ignored sales, how top consulting firms like McKinsey and BCG are shifting their focus, and what the next generation of sales leaders must do to stay ahead in today’s more complex, data-driven world.

Key Takeaways:

Strategy vs. Execution Gap – Too many companies confuse mission statements with actual strategy. A real strategy involves clear choices about where to play and how to win.

Sales is the Most Expensive Agent of Business Strategy – Sales leaders aren’t just there to drive numbers; they’re responsible for aligning execution with corporate goals.

The Planning Problem – Fortune 500 companies often spend 5–9 months on strategy planning, but sales operates in real-time, making many plans outdated before execution even begins.

Financial Acumen Matters – CROs who don’t understand how sales cycles impact working capital and return on assets will struggle to have a seat at the table.

AI’s Role in Sales – AI is rapidly improving lead qualification, sales tracking, and performance management, making data-driven sales leadership more crucial than ever.

Rapid-Fire Q&A with Frank:

Favorite CEO to Follow? – Jamie Dimon (JPMorgan Chase) for his low-BS leadership.

Must-Have Sales Tool? – AI for lead qualification and A/B testing for pricing.

Biggest Lesson from His 20s? – Nobody pays as much attention to you as you do—take ownership of your career.

Favorite Sales Book? – Spin Selling by Neil Rackham.

Favorite Business Book? – The Effective Executive by Peter Drucker.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

On this episode with Paul Melchiorre we discuss:

The Year of Efficiency – How companies are prioritizing enablement, leadership, and strategic decision-making to optimize sales performance.

The Evolution of Sales Enablement – Why traditional training isn’t enough and how sales teams need mentoring, better leadership, and structured processes to succeed.

Pipeline Reality Check – How elite CROs are cleaning up bloated pipelines and leveraging AI to focus on real opportunities.

Outbound Innovation – The changing dynamics of outbound prospecting and why creative, multi-channel strategies are the future.

The Critical Role of Leadership – Why strong CROs and CFOs are shaping the future of B2B sales, and how their alignment impacts business success.

Generational Leadership Challenges – The gap between technical founders, CFOs, and CROs—and why finding the right leader at the right time is harder than ever.

The Next Evolution of SaaS – Are we approaching a post-SaaS era with AI-first platforms? How AI is redefining forecasting, deal qualification, and sales productivity.

Decisive Leadership in Uncertain Times – Why the ability to make fast, strategic decisions is critical in today’s unpredictable market.

Paul also shares his take on the future of sales, the biggest mistakes companies make in hiring leadership, and why adaptability is the #1 trait of successful sales executives.

Don't miss this deep dive into the future of sales efficiency, AI-driven selling, and leadership excellence with one of the industry's most experienced voices!

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, hosts Mark Petruzzi and KK Anderson welcome SaaS industry veteran Paul Melchiorre, a leader in sales transformation, private equity investing, and board advisory. With decades of experience across multiple technology revolutions, Paul shares his insights on the evolving landscape of SaaS sales and what it takes to thrive in today's market.

Key Discussion Topics:

The Changing Buyer Behavior in SaaS – How buyers have become more sophisticated, procurement-driven, and selective in their decision-making.

AI’s Impact on Sales & Business Models – How AI is disrupting traditional SaaS models, from pricing to customer adoption strategies.

The Role of Leadership & Culture in Growth – Lessons from Paul's experience in scaling companies to billion-dollar valuations through IPOs and private equity sales.

The Shift to Efficiency in 2025 – Why the coming year will be about operational efficiency, leveraging technology effectively, and moving beyond the “growth at all costs” mindset.

Customer Success & Expansion Challenges – Why product-led growth alone isn’t enough and how SaaS companies must rethink their approach to customer success and expansion.

Common Mistakes in SaaS Sales – Why sales teams struggle to forecast accurately, fail to differentiate beyond their product, and overlook the broader enterprise objectives of their customers.

Tune in now to learn how to adapt and succeed in the AI-driven SaaS economy!

In Part 2, Paul dives even deeper into the challenges and opportunities in SaaS sales, including the future of GTM strategies, sales team efficiency, and what AI-driven selling really means for revenue leaders. Plus, we discuss the biggest pitfalls to avoid when scaling a SaaS company in 2025. Don't miss it—subscribe now to get notified when the next episode drops!

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode Summary:

In this episode of Selling the Cloud, hosts Mark Petruzzi and KK Anderson sit down with Evan Huck, CEO of UserEvidence, to explore his inspiring journey from an introverted SDR to the leader of a groundbreaking SaaS company. Evan shares the lessons he’s learned about building resilient teams, fostering innovation, and adapting to the rapidly changing sales landscape.

This conversation dives into the shifting dynamics of B2B sales, the rise of evidence-based marketing, and how startups can thrive in unstructured environments. Packed with actionable insights, this episode is perfect for sales professionals, founders, and anyone looking to navigate the future of sales.

What You’ll Learn:

Evan’s Journey: From SDR to SaaS CEO

Discover how Evan’s early sales experiences shaped his leadership philosophy and his approach to building UserEvidence.

The Changing Face of Sales

Learn why traditional sales strategies are becoming less effective and how tools like AI and evidence-based marketing are driving the future.

Building Teams for Unstructured Success

Evan shares his approach to hiring flexible, creative team members who thrive in undefined roles and environments.

Evidence-Based Marketing: The New Frontier

Explore how leveraging customer proof can break through buyer skepticism and build trust in a crowded B2B market.

Founder-Led Sales vs. Scalable Teams

Hear Evan’s tips for transitioning from hands-on selling as a founder to empowering a team to drive growth.

About Evan Huck:

Evan Huck is the CEO and Co-Founder of UserEvidence, a platform transforming how businesses use customer proof to build trust and close deals. Starting as an introverted SDR, Evan’s unconventional career path is a testament to the power of adaptability, curiosity, and a commitment to doing the hard work.

Key Highlights:

• How the SDR role builds critical skills for any sales career.
• Why early-stage startups benefit from employees with diverse, non-traditional backgrounds.
• The importance of consistent experimentation and fostering a culture of learning.
• The role of AI and automation in transforming sales processes.
• Practical advice for navigating the challenges of scaling a startup.

Resources & Links:

• Connect with Evan Huck on LinkedIn.
• Learn more about UserEvidence: www.userevidence.com.
• Books Mentioned:
• Let My People Go Surfing by Yvon Chouinard
• Amp It Up by Frank Slootman
• You Can’t Teach a Kid to Ride a Bike at a Seminar by David Sandler

Don’t Miss Out:

If you enjoyed this episode, subscribe to Selling the Cloud for more insights from the top thought leaders in SaaS. Leave us a review and share the episode with your network!

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.