This episode is the highly anticipated season finale of the Revenue Insiders podcast, hosted by Tiffany Jones and Kelly Lewis. As they wrap up the first season, they provide an insightful and comprehensive recap of the key trends and predictions in the revenue and go-to-market space for 2025 so far. The hosts reflect on the accuracy of their earlier predictions made six months ago, discussing which trends have materialized, which are still pending, and what new developments are emerging as the year progresses.

Tiffany and Kelly dive into the impact of the economy on revenue strategy roles, noting that while some predicted shifts—such as strategy leaders moving into Chief Revenue Officer roles—have been slower to occur, there are signs of gradual change among Fortune 500 companies. They also analyze the much-discussed "Great Resignation 2.0," concluding that while turnover in tech is present, it has not yet reached the expected peak, leaving room for developments in the latter half of 2025.

A major focus of the episode is the rapid evolution of AI and its profound influence on sales, enablement, and customer success. The hosts highlight the explosive growth of product enablement specialist roles, driven by the need to keep pace with AI-enhanced products, with LinkedIn data showing a 58% increase in these roles primarily in tech. They also discuss the balance between AI innovation and non-AI product investments, noting a 22% rise in funding for non-AI tools in Q1 2025, signaling a diversified approach to technology adoption.

Tiffany and Kelly explore the shift towards bite-sized, TikTok-style enablement content, which has seen a remarkable 200% year-over-year growth. This new learning style reflects the need for agility and personalized consumption in adult learning, with many companies adopting short-form enablement to keep teams up to speed in a fast-changing environment.

The episode also covers AI’s growing role in forecasting and post-sales experiences. They share data from Gartner and Forrester revealing that 42% of boards now track AI KPIs and 67% of B2B buyers prioritize seamless AI-human handoffs, underscoring AI’s integration into strategic decision-making and customer interactions. The hosts predict that transparency around AI-driven forecasting will become a critical expectation, with users demanding clear explanations of AI logic and actionable insights to improve outcomes.

Looking ahead, Tiffany and Kelly offer "spicy" predictions for the second half of 2025, including the rise of hybrid human-AI sales teams as a service. They acknowledge the mixed feelings about AI replacing human roles but emphasize the importance of adapting and differentiating through emotional intelligence and thought leadership. They also discuss the challenges of training new sales talent in an AI-augmented world and the evolving nature of sales roles.

Throughout the episode, the hosts share personal anecdotes and industry insights, making complex topics accessible and engaging. They express gratitude to their listeners for their support during the inaugural season and encourage following the podcast on Spotify, Apple, YouTube, LinkedIn, Instagram, and TikTok for continued updates and insights.

This episode is essential listening for revenue leaders, sales professionals, enablement specialists, and anyone interested in the intersection of AI, sales strategy, and market trends in 2025. It offers a rich blend of data-driven analysis, expert predictions, and practical advice to navigate the fast-paced changes shaping the future of go-to-market strategies.

TL;DR: Kelly Lewis and Tiffany Jones go deep on imposter syndrome—how it shows up in go-to-market roles, what it feels like as a VP, and how they’ve learned to manage it. This is a must-listen for anyone navigating career growth, leadership transitions, or high-stakes roles in sales, marketing, or RevOps.

In this candid, heartfelt episode of The Revenue Insiders, it’s just your two co-hosts—no guests, no filters. Kelly and Tiffany recorded this one after Tiffany’s recent promotion to SVP and Kelly’s transition into full-time entrepreneurship, so the timing couldn’t be better.

They break down:

• Why imposter syndrome is so common in GTM roles

• The difference between confidence and self-doubt

• Coping mechanisms that actually work (spoiler: it’s not just power poses)

• What leaders can do to create psychological safety for their teams

• Why you should apply for that job—even if you don’t meet all the requirements

• And yes, Kelly finally owns the title “Founder”

You’ll hear real stories—from 24-year-old Tiffany selling to CEOs, to Kelly’s first time saying “I’m a co-founder”—plus plenty of tactical tips for how to manage the internal voice that tells you you’re not ready.

Whether you’re an SDR, a VP, or somewhere in between, this episode is your reminder: you’re not alone, you’re more capable than you think, and it’s all going to be okay.

🔗 Follow, rate, and share if this hit home.

🎧 Available on Spotify, Apple, and YouTube.

imposter syndrome, go-to-market, GTM careers, revenue leadership, psychological safety, sales enablement, founder journey, women in leadership

TL;DR: What do military leadership, AI strategy, and revenue forecasting have in common? According to Andy Champion, everything. In this episode of The Revenue Insiders, Andy joins Kelly and Tiffany to talk about people-first leadership, building inclusive GTM teams, and how AI is transforming B2B sales—without replacing the human advantage.

Andy Champion, VP & GM of EMEA at 6sense (and former sales leader at Highspot, Yext, and DocuSign), shares battle-tested insights from both the military and the boardroom. From servant leadership to situational coaching, Andy unpacks the nuance behind high-performing, psychologically safe revenue teams.

In this episode:

• Why psychological safety drives discretionary effort and retention

• How to manage accountability without micromanaging

• A military lesson that still shapes Andy’s leadership style

• The sales leader’s role in creating a sense of belonging—especially in global teams

• How AI enhances, not replaces, sales strategy and research

• The real difference between Europe and “EMEA”—and how to avoid costly expansion mistakes

Whether you’re a frontline manager, a GTM exec, or expanding into new markets, this episode will challenge you to lead more intentionally and observe more closely.

Mentioned in this episode:

• 6sense AI-powered GTM platform

• Servant leadership and the power of consistency

• Situational leadership frameworks

• Forecasting with AI

• Partner strategy in international growth

TL;DR: Partner-led growth isn’t just a strategy—it’s a cultural mindset. In this episode of The Revenue Insiders, Kelly and Tiffany talk with Bill Glenn, five-time CMO and current marketing leader at Esper, about how B2B companies can unlock scalable growth by treating partners as an extension of the revenue team. From avoiding attribution headaches to enabling reps with TikTok-style video snippets, Bill brings hot takes and real playbooks on how to go partner-first without losing control.

In this episode, we cover:

• What “partner-led growth” really means in a B2B context—and how it’s different from channel sales
  

• Why company size isn’t the best indicator of readiness (and what to consider instead)
  

• Common missteps in building partner programs (and how to avoid “if you build it, they will come” traps)
  

• Why executive alignment is non-negotiable before launching a partner strategy
  

• Gamification vs. certification: What works best to engage partner sellers
  

• How to enable both internal teams and external partners without creating confusion
  

• A fresh take on attribution, KPIs, and why Bill’s blood pressure rises every time “attribution” is mentioned
  

• Why partner involvement in renewals is a strategic advantage—and how to use it for multi-threading
  

Bill also shares career reflections from his five-time CMO journey, and offers a mindset-flipping question that’s reshaped how he leads: “What’s the best that can happen?”

If you’re building or rethinking a partner strategy, this episode is your tactical blueprint.

📲 Follow The Revenue Insiders on LinkedIn for more B2B growth insights.

TL;DR:

Natalie Wolf, VP of Customer Success at People.ai, joins Kelly and Tiffany for a candid conversation about career growth, stepping into your power, operationalizing customer outcomes, and how AI is changing go-to-market for good. If you want tactical advice for thriving in today’s chaotic GTM world, this episode is a must-listen.

Full Description:

In this episode of The Revenue Insiders, we sit down with Natalie Wolf, VP of Customer Success at People.ai, to explore the future of customer success, AI, and go-to-market leadership. Natalie’s story is proof that career success isn’t handed to you—you have to step into your power and create it.

Natalie’s journey started in consulting, where she built an obsession with operational excellence and solving for pain. Later, she transitioned into customer success leadership, not by waiting for a promotion, but by spotting a gap at Anaplan and declaring a new path forward. She shares how stepping into an undefined role, without permission or playbook, helped her build a customer success function from scratch—and why today’s leaders must do the same if they want to stand out.

A few key themes we explore:

• Leadership isn’t about being the smartest person in the room—it’s about unlocking others’ superpowers.

• Revenue growth is a team sport—CS, sales, and support must drive shared outcomes, not siloed KPIs.

• AI is powerful only when tied to real, painful workflows—not hype.

• Career opportunities today are hidden inside messy, unstructured problems, not job postings.

Natalie drops an important truth: Too many leaders use AI as a shortcut instead of solving fundamental go-to-market problems. She shares how People.ai embeds AI into critical rituals—like customer health scoring and value reviews—to drive meaningful outcomes, not just automate busywork.

We also dive into Natalie’s personal process for evaluating career moves (hint: it’s way more thoughtful than most people’s). She breaks down why product-market fit, culture, executive alignment, and stage-appropriateness matter—and why a great brand name or big title should never be enough.

And it wouldn’t be a Revenue Insiders episode without a little humor:

• Kelly shares her firm policy of paying someone else to take her kids to Disneyland.

• Natalie proudly embraces her status as a Disney adult—with spreadsheets to prove it.

• Tiffany and Natalie bond over their shared obsession with planning (and purple leopard aerobics outfits).

If you’re a:

• GTM professional worried about staying relevant

• CS leader navigating this volatile economy

• Sales or CS practitioner trying to embed AI into real outcomes

• Rising leader wondering how to create your next opportunity

—this conversation will hit home.

Natalie leaves listeners with a powerful challenge:

🎧 Tune in to hear why simplicity wins, why declaring your leadership is non-negotiable, and how operationalizing outcomes—not just activities—can future-proof your career in 2025 and beyond.

“What’s the one shared customer outcome you could align your entire go-to-market team around today—and how would it change your revenue path?”

In this insightful episode of Revenue Insiders, hosts Tiffany Jones and Kelly Lewis sit down with Trisha Ponce, a Solutions Engineer (SE) at Salesforce, to explore the rapidly evolving intersection of artificial intelligence, sales engineering, and customer success.

The conversation opens with Trisha demystifying Agent Force, Salesforce’s AI platform designed to deploy intelligent agents across business functions. Trisha explains how these AI agents can assist human employees, automate research and repetitive tasks, and even act autonomously to resolve customer inquiries-only escalating to human teams when necessary. This shift is not just about efficiency; it’s about redefining the very nature of work and customer engagement.

As the dialogue unfolds, Tiffany and Kelly probe the changing role of the solutions engineer. Trisha shares her unique journey from accidental Salesforce admin to SE, highlighting how today’s sales engineers must bridge deep technical expertise with business acumen. With AI and data-driven products like Data Cloud moving away from traditional seat-based pricing to complex consumption-based models, SEs are now integral to both the technical and commercial aspects of the sales process. This requires a new level of collaboration between sales and technical teams, as well as a constant commitment to learning and adaptation.

The episode delves into the practical realities of selling and implementing AI solutions. Trisha discusses the learning curve Salesforce teams have faced in adopting consumption-based pricing, emphasizing the need to deeply understand each customer’s data, use cases, and expected outcomes. She describes this new model as both an art and a science, requiring careful estimation, ongoing monitoring, and a willingness to adjust as real-world usage unfolds.

Listeners are treated to real-world examples of AI agents in action-from out-of-the-box templates for marketing, sales coaching, and service, to custom-built agents like quoting assistants and deal desk bots. Trisha introduces the Agent Exchange, Salesforce’s marketplace for AI agent solutions, where partners can share innovations and customers can find ready-made tools to accelerate their AI journey.

The discussion also addresses the challenges and concerns customers face, particularly around trust, security, and transparency. Trisha reassures listeners that Salesforce’s platform is designed to prevent prompt injection attacks, minimize hallucinations, and ensure that AI agents are always clearly identified-never masquerading as human employees. She advises starting with internal use cases to build comfort and confidence before rolling out customer-facing agents.

In a lighter moment, the trio debates the etiquette of saying “please” and “thank you” to AI, reflecting on the broader implications of humanizing technology and the importance of clear, direct communication with both machines and people.

Beyond technology, Trisha shares her creative side-hand-painting Salesforce-themed shoes for company events-and recounts her career journey from accounting and logistics to sales ops and, ultimately, to Salesforce. Her story underscores the value of curiosity, adaptability, and a passion for solving real customer problems.

The episode closes with Trisha’s challenge to listeners: “How can you make your life or your customers’ lives easier by leveraging this technology? And how can you ensure you’re at the forefront of implementing and shaping these changes?” In a world where AI is moving fast, staying curious, proactive, and informed is essential for anyone looking to lead rather than follow.

Whether you’re a sales professional, a technical leader, or simply curious about the future of AI in business, this episode offers a candid, practical, and inspiring look at what’s next for sales engineering and customer success in the age of intelligent agents.

TLDR;

- The importance of self-assessment and vulnerability in leadership development

- How to leverage AI as a tool for empathy, not just efficiency

- Strategies for integrating EQ into hiring, coaching, and team-building

- The necessity of continuous feedback and adaptation as personal and business priorities evolve

In this thought-provoking episode of Revenue Insiders, hosts Kelly Lewis and Tiffany Jones sit down with Darren Brady, VP of Sales at RevShop, to explore the dynamic intersection of Emotional Intelligence (EQ) and Artificial Intelligence (AI) in today’s go-to-market landscape.

Darren shares candid stories from his own career, highlighting the challenges and rewards of balancing intellectual intelligence (IQ) with emotional intelligence (EQ) on sales teams. He describes the difficulties leaders face when managing individuals who excel in product knowledge but struggle with empathy, and vice versa. Through personal anecdotes, Darren emphasizes that great leadership isn’t about being perfect in every area, but about understanding your own strengths and weaknesses—and building teams that complement and fill those gaps..

Kelly and Tiffany echo these insights, recounting experiences with EQ-focused assessments and executive coaching. They discuss how self-awareness, vulnerability, and the willingness to delegate or seek help are crucial skills that distinguish truly effective leaders from those who plateau. The group agrees: as organizations grow, leaders must move beyond the “superhuman” mentality and embrace the power of collective intelligence and emotional honesty.

The discussion pivots to the role of AI in modern sales and business operations. Darren observes that while AI tools are proliferating—often in the form of “co-pilots” and productivity boosters—many organizations are missing the mark by failing to integrate these technologies into the natural flow of work. Instead of replacing human sellers, Darren argues, AI should be used to eliminate mundane tasks, surface actionable insights, and free up time for what humans do best: building relationships and telling stories[1].

Tiffany and Kelly add that AI’s real power lies in its ability to augment empathy at scale. For example, AI can help craft more empathetic communications, detect emotional states in digital interactions, and provide feedback loops that help teams continuously improve. However, they caution that technology alone cannot substitute for genuine human understanding; it must be thoughtfully woven into workflows and supported by a culture of emotional intelligence.

As remote work and digital-first interactions become the norm, the panel delves into the unique challenges facing parents and caregivers in leadership roles. Darren reflects on how becoming a father has deepened his empathy for colleagues navigating similar situations, and how supportive company cultures can make all the difference. The hosts agree that leading with empathy—recognizing employees as whole people, not just productivity units—is essential for building resilient, high-performing teams in today’s volatile environment[1].

Darren closes the episode with a powerful challenge:

“What’s important to you—right now, in this season of your life and career? Don’t be afraid to let that answer change, and let it guide how you lead, collaborate, and embrace both technology and humanity in your work.”

This episode is essential listening for leaders, sales professionals, and anyone navigating the rapidly changing intersection of human connection and artificial intelligence. Discover how EQ and AI together can unlock new levels of performance, empathy, and growth in your organization.

TL;DR:

This episode is all about the unsung heroes of the sales world: Sales Engineers (SEs). Hosts Kelly Lewis and Tiffany Jones, joined by guest Sachin Wadhawan, explore the vital partnership between Account Executives (AEs) and SEs—framed through the lens of Batman and Robin. They break down what makes this relationship tick, why it’s essential for winning bigger, better, and faster deals, and how organizations can better support and recognize their SEs.

Sales Engineers are the secret weapon behind every successful sales team, but their contributions are often misunderstood or overlooked. In this lively episode, Kelly and Tiffany welcome Sachin Wadhawan—author of "Trust Your SE: Sell Bigger, Better and Faster with Sales Engineering" and host of the Coffee with Sales Engineers podcast—to shine a spotlight on the SE role.

Drawing on Sachin’s deep experience and passion for sales engineering, the conversation uses the Batman and Robin analogy to illustrate the unique, symbiotic partnership between AEs and SEs. Just as Batman and Robin each bring their own strengths to crime-fighting, AEs and SEs complement each other to deliver value to customers and close deals. Sachin shares why he’s always embraced the “Robin” role, emphasizing that both sides need to understand and respect what motivates the other for the partnership to thrive.

SEs aren’t just driven by commissions or accolades—they’re problem-solvers at heart, energized by complex challenges and the opportunity to wow customers with creative solutions.

Why the best sales outcomes happen when AEs and SEs operate as true partners, each playing to their strengths and trusting each other to handle their part of the sales cycle.

The importance of open dialogue between AEs and SEs—including how to give feedback, correct mistakes in front of customers without damaging credibility, and develop that unspoken “demo dance” chemistry in meetings.

How AI and automation are changing the landscape, but why the human element of the SE is irreplaceable. Sachin argues that AI should be used to offload repetitive tasks, freeing SEs to focus on high-impact customer interactions—like a surgical team prepping the OR so the surgeon can focus on the operation.

Insights on how organizations should think about AE-to-SE ratios, the impact on deal quality, and why SEs often lack the investment and recognition they deserve.

The best SEs don’t always come from technical or sales backgrounds—curiosity, problem-solving, and the ability to build trust are what matter most. Kelly, Tiffany, and Sachin discuss creative ways to identify and nurture SE talent from diverse industries.

Why it’s crucial to celebrate SE wins, include them in President’s Club, and provide dedicated training and career development—rather than just relying on them to train others.

Whether you’re an AE, SE, sales leader, or just curious about the Batman-and-Robin magic behind high-performing sales teams, this episode delivers practical insights, candid stories, and a fresh appreciation for the sales engineer’s craft.

Don’t miss this deep dive into the heart of sales engineering—where every great Batman needs their Robin, and every deal needs its dynamic duo.