SaaS Backwards - Reverse Engineering SaaS Success

Guest: Guy Rubin, Founder & CEO at EbstaMost B2B SaaS leaders know their top performers carry the team, but few understand why the performance gap keeps widening.The reality is that just 14% of reps are now responsible for 80% of revenue, and the gap between A-players and everyone else has grown to 11x. Fixing this isn’t about more training or new tools—it’s about creating consistent, data-driven sales execution across the entire go-to-market team.In this episode, Guy Rubin, Founder & CEO of Ebsta, shares insights from the 2025 B2B GTM Benchmark Report (in partnership with Pavilion) and explains how SaaS companies can close the performance gap, improve forecast accuracy, and drive revenue by making data and behavior work together.Key Takeaways:Top Performers Win with Consistency: The biggest gap isn’t talent—it’s execution at every stage of the funnel.AI Enables Better Selling, Not More Noise: When AI is used to extract insights, not automate spam, it becomes a game-changer.Full-Cycle Reps Are Back: 45% of companies are ditching the SDR model in favor of holistic sales ownership.Engagement Drives Forecast Accuracy: Momentum scoring predicts risk before it’s too late to course-correct.Success = Process + Behavior + Data: Sales isn’t just about gut feel anymore—it’s finally becoming data-driven.Guy offers CROs and CMOs a blueprint to scale what works, eliminate what doesn’t, and win more consistently—making this episode a must-listen.---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Guest: Srikrishnan Ganesan, Co-Founder & CEO of RocketlaneMost B2B SaaS leaders know that onboarding is important but underestimate its impact.The reality is that 97% of churn at first opportunity is decided in the first 90 days, making onboarding the most critical stage in the customer journey and the defining factor in revenue growth and long-term customer success.In this episode, Sri Ganesan, Co-Founder and CEO of Rocketlane, shares how SaaS companies can transform onboarding from a fragmented process into a strategic advantage. From community-led growth to automation-driven efficiency, he reveals what top SaaS companies do differently to drive retention, expansion, and revenue acceleration.Key Takeaways:Onboarding Determines Retention & Growth: The first 90 days define whether customers will churn or expand.Community-Led Growth Builds Credibility: Building an engaged audience before launch fosters trust and momentum.Automation Eliminates Inefficiency: Siloed tools slow teams down; all-in-one platforms drive success.Market Validation is Critical: The biggest factor in startup success isn’t the product—it’s picking the right market. Sri shares actionable strategies for SaaS CMOs and CROs to create onboarding experiences that drive retention, expansion, and revenue acceleration—making this episode a must-listen.---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Guest: Christina Richards, Fractional CMO & Author of Rise of the AI-Powered CMOMost B2B marketers think they’re using AI effectively. The reality? Many are barely scratching the surface—and failing to leverage AI as a true revenue driver.Christina Richards, fractional CMO and author of Rise of the AI-Powered CMO, breaks down how AI is transforming go-to-market strategies, reshaping demand generation, and redefining the role of marketing leaders in B2B SaaS.The biggest shift? AI is moving from a tool for efficiency to an autonomous operator, changing how marketers engage customers, optimize campaigns, and drive pipeline growth. Those who fail to adapt will fall behind competitors who are already leveraging AI-driven personalization, predictive lead scoring, and hyper-targeted ad strategies.Christina shares actionable insights on how B2B CMOs and CROs can embrace AI—not just for automation, but as a strategic advantage to accelerate growth and revenue.Key Takeaways:AI is Now Critical Infrastructure: It’s no longer just a tool for automation—it’s transforming how companies generate revenue.CMOs Must Become Revenue Architects: The role of marketing leaders is shifting from brand builders to full-funnel revenue drivers.AI-Driven Search is Changing SEO: If your content isn’t optimized for AI-generated search, your audience may never find you.Agentic AI is Here: Autonomous AI agents are moving from experiment to execution—marketers must prepare now.First-Party Data is a Competitive Advantage: With hyper-personalization on the rise, companies that don’t own their audience data will struggle to compete.Get ready to rethink your marketing strategy in the age of AI—or risk being left behind.---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Guest: Zach Wright, Co-Founder & CRO of Syft AIMost sales teams are still stuck in outdated prospecting tactics—mass email sequencing, generic outreach, and hoping something sticks. The reality? These methods are failing fast, and sellers who rely on them are drowning in low response rates and missed pipeline goals.Zach Wright, co-founder and CRO of Syft AI, breaks down why traditional sales prospecting is broken and what today’s B2B SaaS sellers must do differently to cut through the noise, engage decision-makers, and win more deals.The biggest mistake? Relying on volume instead of relevance. Buyers are overwhelmed with hundreds of templated emails daily, and most outreach feels impersonal, irrelevant, and easy to ignore. Instead of spamming prospects, Zach shares how AI-driven prospecting helps sales teams pinpoint the right accounts, at the right time, with the right message.He explains how top sales teams are:✅ Ditching “spray and pray” prospecting in favor of targeted, intent-driven outreach.✅ Using AI to surface active buying signals—so reps only reach out when there’s a real need.✅ Personalizing at scale without relying on ineffective AI-generated fluff.✅ Bringing cold calling back—and why it’s working better than ever.If your outbound efforts aren’t converting like they used to, this episode will change the way you think about prospecting—and show you how to start winning more meetings with high-value prospects.---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Guest: Peter Cohan, Author of Doing DiscoveryMost sales teams think they’re great at discovery. The reality? About 80% are getting it wrong—and it’s the single biggest reason why deals stall, go to a competitor, or die with “no decision.”Peter Cohan, author of Doing Discovery, breaks down why traditional discovery methods are failing and what SaaS sales teams must do differently to uncover real customer value, build compelling business cases, and stop losing winnable deals.The biggest mistake sellers make? Rushing to the demo before fully quantifying business pain. If you can’t pin down the numbers behind a buyer’s problem and desired outcome, you’re making it nearly impossible for them to justify the purchase—let alone get buy-in from their team.Peter shares practical strategies to flip the script on outdated discovery calls, avoid the “interrogation” trap, and use discovery to drive urgency, not just collect pain points.Key Takeaways:✅ Uncover the Value Gap: The secret to avoiding “no decision” isn’t just probing for pain—it’s quantifying the gap between today’s reality and the desired future state.✅ Vision Reengineering: Most buyers don’t know what they don’t know. Learn how to introduce new ideas without losing control of the deal or giving away discounts.✅ Turn Discovery Into a Two-Way Conversation: Stop making prospects feel like they’re on trial—use quid pro quo techniques to make discovery a collaborative process.Get ready to rethink how you approach discovery—or risk losing more deals than you should.---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Guest: Ty Tinker, Head of Analytics at AdQuickWhat if everything you thought about billboard advertising was wrong?Ty Tinker, Head of Analytics at AdQuick, breaks down the myth that out-of-home (OOH) advertising is unmeasurable and outdated. In reality, leading SaaS companies—including Dropbox, Salesforce, and Shopify—are embracing billboards, transit ads, and airport placements to drive brand awareness, accelerate sales cycles, and even generate measurable leads.Ty reveals how brands are leveraging data science, AI, and sophisticated measurement techniques (beyond old-school QR codes) to track campaign performance. He also shares why smart SaaS marketers are treating OOH as a long-term investment, not just a one-off trade show play.Key Takeaways:📊 Out-of-Home Can Be Measured: Advances in mobile device tracking, mixed media modeling (MMM), and causal inference are proving OOH’s impact on website traffic, MQLs, and pipeline growth.🚀 Credibility Wins Deals: Buyers shortlist SaaS vendors before ever visiting a website. Strategic OOH placements—especially at airports and conferences—ensure your brand is top of mind when it matters most.🎯 The Right Placement Changes Everything: SaaS brands like Shopify and Shield AI are hyper-targeting decision-makers using billboards in high-traffic business areas, conference zones, and even airport walkways.Want to see if out-of-home advertising fits your go-to-market strategy? Tune in now!---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Guest: Jon Miller, Co-Founder & CEO of a Stealth AI StartupJon Miller, co-founder of Marketo and former CMO of Demandbase, argues that B2B marketing’s traditional playbook—built on predictable demand generation, MQL scoring, and SDR-driven outbound—is broken. The “gumball machine” approach, where marketers expect predictable revenue by simply feeding in budget and campaigns, no longer works. Buyers have evolved, becoming more resistant to outbound tactics and opting for anonymous research. To succeed, revenue leaders must shift from short-term lead generation to long-term brand building, customer experience, and relationships.Key Takeaways:🔹 The Death of the MQL Machine: Buyers have learned to avoid traditional lead capture tactics, making it essential to rethink how marketing contributes to revenue​.🔹 Brand Awareness > Lead Generation: The most successful companies focus on being top-of-mind when buyers do enter a purchasing cycle, rather than scrambling to capture leads in the moment​.🔹 AI Will Kill the Old Content Playbook: The rise of AI-driven search and inbox filters means generic, mass-produced content won’t cut it. Instead, companies need to invest in original research, experiences, and trusted relationships​.🔹 New Metrics for Marketing Success: Instead of obsessing over short-term pipeline metrics, CMOs should measure brand perception within key accounts, engagement quality, and community strength​.This episode is a must-listen for SaaS revenue leaders struggling to adapt their go-to-market strategy in a world where buyers don’t want to be sold to.---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Kerry Cunningham, Head of Research at 6Sense, shares insights from the Buyer Experience Report 2024. He uncovers the new B2B buyer behavior where 85% of buyers lead conversations on their own terms. His key points emphasize the importance of demand generation over traditional lead capture strategies. With buyers already knowing their options, companies must position themselves effectively to make the shortlist. Additionally, he highlights the crucial role analysts play in the decision-making process, urging marketers to adapt their tactics accordingly.

Guest: Maxwell Nee, CRO at ScoreAppMaxwell Nee, Chief Revenue Officer of ScoreApp, shares the strategies behind scaling a low ARR SaaS product to 9,000 paying customers worldwide. By leveraging the principles of quiz marketing, ScoreApp turns engagement into actionable insights, driving top-of-funnel lead generation, accelerating sales cycles, and refining customer experiences. The platform’s success stems from a relentless focus on understanding user needs before development, validating concepts with 3,000 prospects prior to launch, and building personalized, gamified experiences that deliver measurable value.Maxwell’s perspective on SaaS growth is rooted in actionable principles: prioritize customer input, focus on enterprise value over personal branding, and invest in scalable systems. His advice for marketing leaders emphasizes clarity in messaging, the importance of simple, compelling copy, and always aligning content with the needs and emotions of the target audience.Key Takeaways:Focus on Validation: ScoreApp validated its concept with 3,000 prospective users before launch, ensuring a strong product-market fit from the start.Personalization and Gamification Drive Results: Interactive quizzes generate higher engagement and conversion rates by combining self-discovery with actionable insights.Clarity Over Complexity: Simplifying messaging and focusing on the audience’s pain points can significantly boost engagement and lead generation.---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

Guest: Ken Lempit, President & Chief Business Builder at Austin Lawrence GroupIn this episode, Austin Lawrence Group’s Ken Lempit shares a bold approach to overcoming the inefficiency of traditional advertising campaigns. He emphasizes a new strategy: combining foundational customer interviews with rapid, real-time testing via high-frequency organic social media posts. This iterative approach helps identify messaging that resonates most with target audiences before significant ad spend, enabling SaaS companies to avoid costly missteps. Lempit calls out outdated "ivory tower" methods, where messaging was developed in isolation and assumed durable for years. Today, he argues, messaging must evolve constantly based on audience engagement.Key Takeaways:Real-Time Validation Beats Guesswork: Test messaging in organic social media environments before committing ad budgets. Insights from live engagement can refine campaigns and improve ROI.Messaging Is No Longer Durable: Static messaging fails in today’s dynamic market. Iterative testing ensures campaigns stay relevant and effective.Drive Action with the Cost of Inaction: Instead of focusing on ROI, highlight the risks of staying in the status quo to compel prospects to act.This practical framework bridges the gap between creative intuition and data-driven decisions, setting a new standard for SaaS advertising.Other resources to check out:Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes a yearly report about how B2B buyer behavior is changing.The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.