Rick Smolen Says AI Is a Leverage Tool

The "art" of sales — human connection, curiosity, and deep personal research — is surging back to the forefront as AI commoditizes transactional GTM motions.

📊 10 episodes across 7 podcasts

⏱ 481 minutes of intelligence analyzed

🎙 Featuring: Jen Abel, Lenny Rachitsky, Lenny, Sam Jacobs

The Big Shift

AI's accelerating impact on Go-to-Market is paradoxically highlighting the irreplaceable value of human elements in sales and marketing. While AI is celebrated for efficiency, the most impactful shifts are occurring where human intuition, relationship-building, and deep problem diagnosis are amplified, not replaced. This means a renewed focus on the 'art' of sales, where genuine connection and curiosity differentiate winning strategies.

The New Divide: AI is quickly becoming a leverage tool, as described by Rick Smolen, CRO of ShipHero, who noted, "AI is a leverage tool. It's like debt, like debt is leverage. It can make performance exceptionally good or it can bankrupt you." It excels at process, data analysis, and efficiency, but founders and CROs are stressing that it's not a shortcut for foundational GTM skills. AI struggles with the "unwritten rules" of human interaction, emotional intelligence, and complex problem diagnosis that define high-value deals.

Human Edge: Jen Abel, Co-founder of JJellyfish, highlights that "The most successful salespeople are not trained salespeople. That's why founders are so good at this." Their strength lies in extracting "alpha"—unique, nuanced intelligence—not in scripting or following rigid processes. This aligns with Michelle Bove's emphasis on "likability" and "human connection" as crucial sales competencies. John Barrows, CEO of JB Sales, underscores the importance of the "give a shit factor," stating, "until you start actually giving a shit about the person that you're reaching out to and think of them as a person, not a sequence you have to send, not a call you have to make... your results aren't going to change."

Strategic Application: The real challenge, and opportunity, is integrating AI to enhance these human strengths, not to bypass them. Mike Carpenter, CEO of XFactor.io, cautions against the misuse of generic LLMs on CRM data, as they "completely hallucinate an answer, but it doesn't just hallucinate a drifted answer, it gives it to you with certainty." This emphasizes the critical need for human judgment and causal AI for truly reliable insights, preserving the human role in validating and acting upon AI-generated intelligence. The shift is not about AI versus humans, but about how AI empowers a more human, value-driven approach to GTM.

"The most successful salespeople are not trained salespeople. That's why founders are so good at this."
— Jen Abel, Co-founder of JJellyfish and GM of Enterprise Sales at State Affairs on Lenny's Podcast: Product | Career | Growth

The Rundown

① Pricing is a Product Roadmap Component, Not an Afterthought.

AI pricing is fundamentally different from traditional models, requiring integration into the product roadmap from the very beginning. Manu Mehra, Head of AMER Industries Strategic Deal Pricing at Databricks, argues that "Pricing cannot be an afterthought. Like pricing needs to be integrated during the product roadmap."

→ Strategic Insight: Successful AI solutions demand outcome-based pricing, which necessitates segmenting customers and packaging offerings to solve specific business problems, making pricing an iterative design challenge rather than a post-launch decision.

② CROs are Prioritizing "Return to Traditional" Sales Methods Over AI Hype.

Despite significant AI investment, leading sales organizations are reverting to classic problem-solving methodologies championed by figures like John McMahon, focusing on customer problem diagnosis rather than solely product features. Rick Smolen, CRO at ShipHero, stated that "sales used to be, it used to be you won if you were an expert in your product... The winner is in somebody that can actually diagnose the problem better than the actual buyer can do it themselves."

→ Key Implication: While AI offers efficiency gains, foundational sales skills—like understanding customer needs and providing solutions—remain paramount, challenging the narrative of immediate, transformative AI productivity.

③ Shaping Willingness to Pay (WTP) is More Powerful Than Measuring It.

Companies can actively influence buyers' Willingness to Pay through strategic actions like economic value estimation, rather than passively measuring it with traditional methods. Mark Stiving, Host of Impact Pricing, asserts that "Willingness to pay is a decision, and decisions can be shaped."

→ Actionable Strategy: Pricing leaders should focus on demonstrating differential value against competitors and aligning pricing models with the value buyers receive, making price feel smaller relative to the outcome.

④ Authenticity and Human Connection Define Modern Outbound Success.

In an age of AI-generated content, genuine personalization, empathy, and a "give a shit" attitude toward prospects are critical for cutting through the noise in outbound sales. John Barrows, CEO of JB Sales, highlighted the need to treat prospects as people, not just "a sequence you have to send."

→ Talent Development: Sales teams need to invest in developing deeper research skills and emotional intelligence to build rapport, especially as AI-driven automation commoditizes generic outreach.

⑤ Enterprise Sales is a 15-Step Process, Not a 5-Step CRM Pipeline.

The common five-stage CRM pipeline is primarily for forecasting, not an accurate representation of the intricate, multi-stage process required to close large enterprise deals. Jen Abel, Co-founder of JJellyfish, states, "Most people think the sales process is five steps and we're already in step 10 and we're not even done."

→ Operational Realization: Teams engaging in complex sales must adopt detailed, tactical playbooks—like the "pincer model" for initial outreach and "follow-up intro calls" for intelligence gathering—to manage the true complexity of enterprise sales motions.

Signal Board

🔥 HEATING UP

• Likability in Sales: Emphasized as an underrated competency, crucial for building champions and executive relationships. (Michelle Bove on Revenue Builders)

• Causal AI for sales planning: Utilized to build "always-on" operating plans that adapt to changing market conditions, moving beyond static spreadsheets. (Mike Carpenter on Topline)

• Targeting Non-LinkedIn B2B Buyers: High growth opportunities exist in industries where buyers aren't on traditional platforms, requiring unique channel strategies. (Clare Corriveau on The Dave Gerhardt Show (from Exit Five))

• Vertical integration for space infrastructure: Essential for controlling unit economics in ambitious projects like orbital data centers. (Baiju Bhatt on Grit)

👀 ON WATCH

• AI for lead generation and account-based marketing: Revolutionizing targeting and campaign effectiveness but not necessarily tripling sales results. (Rick Smolen on Topline)

• The 'give a shit' factor in sales: A core value differentiating successful salespeople from those relying on impersonal, AI-driven sequences. (John Barrows on GTM Science - A show for GTM and RevOps leaders)

• AI sales paradigm shift: Moving from certainty to curiosity and experimentation, especially in post-signature workflow discovery. (Seong Park on Revenue Builders)

• Human intervention in AI validation: Critical for ensuring accuracy and trust, especially as LLMs can "hallucinate with certainty." (Mike Carpenter on Topline)

❄️ COOLING OFF

• Critique of LLM use on CRM data: Using generic LLMs on CRM data can lead to confidently incorrect answers that remain undetected until business performance suffers. (Mike Carpenter on Topline)

• SDR model: Often viewed as unprofitable when analyzed as a standalone function, challenging its perceived value in sales development. (John Barrows on GTM Science - A show for GTM and RevOps leaders)

• Top-down AI adoption fails: Corporate AI initiatives often fail due to a lack of organizational engagement and bottom-up buy-in. (John Barrows on GTM Science - A show for GTM and RevOps leaders)

The Bottom Line

Amidst the AI gold rush, GTM leaders are finding that sustained success comes from augmenting human ingenuity and connection, not replacing it, with disciplined, customer-centric strategies winning the day.

Quick Appendix

GTM Science - A show for GTM and RevOps leaders: "What's Actually Working in Outbound Right Now with John Barrows" · 59 min · Featuring John Barrows ▶ Listen · Apple Podcasts

For Revenue Leaders: This episode provides a grounded perspective on AI's current impact on outbound and critical human elements of sales success.

Grit: "Data Centers in Orbit by 2028: Baiju Bhatt on His Plans After Robinhood" · 73 min · Featuring Baiju Bhatt ▶ Listen · Apple Podcasts

For Visionary Entrepreneurs: Insights into extreme vertical integration and "good problems" of hypergrowth in deep tech.

Impact Pricing: "Buyer Insight: Stop Measuring WTP. Start Shaping It." · 4 min · Featuring Mark Stiving ▶ Listen · Apple Podcasts

For Product & Pricing Strategists: A concise argument for proactive pricing strategies that shape, rather than just measure, buyer willingness to pay.

Impact Pricing: "What Are You Really Charging For? The Business Problem Behind AI Pricing with Manu Mehra" · 32 min · Featuring Manu Mehra ▶ Listen · Apple Podcasts

For Product & Pricing Strategists: Unpacks the complexities of AI pricing, emphasizing integration with product roadmaps and outcome-based models.

Lenny's Podcast: Product | Career | Growth: "How to close $100K+ enterprise deals, step by step | Jen Abel" · 85 min · Featuring Jen Abel ▶ Listen · Apple Podcasts

For Enterprise Sales Professionals: A deep dive into the nuanced, multi-step process of closing large enterprise deals, debunking common misconceptions.

Revenue Builders: "AI Selling Rewards Curiosity | Workflow Discovery with Seong Park" · 10 min · Featuring Seong Park ▶ Listen · Apple Podcasts

For Sales Leaders & AI Implementers: Focuses on the shift to curiosity and workflow discovery in AI selling and the importance of post-signature engagement.

Revenue Builders: "How to Hire Better Salespeople Than Yourself and Lead Them to Win" · 67 min · Featuring Michelle Bove ▶ Listen · Apple Podcasts

For Sales Leaders: Practical advice on hiring for likability, coaching effectively, and balancing the "science" and "art" of sales.

The Dave Gerhardt Show (from Exit Five): "Marketing to B2B buyers who aren't on LinkedIn (with Clare Corriveau, VP Marketing, Tekmetric)" · 47 min · Featuring Clare Corriveau ▶ Listen · Apple Podcasts

For B2B Marketers: Provides a unique perspective on marketing to niche, "non-desk" B2B buyers and strategic talent orchestration.

Topline: "SPOTLIGHT: He Missed Quota 5 Times in 25 Years. Here's the System Behind That.| Mike Carpenter, CEO & Co-Founder @ Xfactor" · 30 min · Featuring Mike Carpenter ▶ Listen

For Sales & RevOps Leaders: Insights into data-driven sales "cheat codes" and the crucial role of causal AI with human intervention.

Topline: "The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero" · 74 min · Featuring Rick Smolen ▶ Listen

For CROs & Sales Leaders: Navigating AI's role as a leverage tool and the importance of returning to traditional enterprise sales methodologies.