SaaS Backwards - Reverse Engineering SaaS Success

Guest: Christina Richards, Fractional CMO & Author of Rise of the AI-Powered CMO

Most 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.

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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 AI

Most 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.

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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 Discovery

Most 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.

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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 AdQuick

What 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!

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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 Startup

Jon 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.

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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: Kerry Cunningham, Research & Thought Leadership at 6sense 

85% of buyers initiate the first conversation with vendors—on their terms. If your marketing still revolves around capturing leads and pushing outbound sales, you're already behind.

Kerry Cunningham, Head of Research at 6Sense, shares insights from their Buyer Experience Report 2024, revealing how today’s B2B buyers operate—and why most SaaS companies are out of sync. 

Buyers come into the process knowing who they’ll evaluate, and 90% of the time, they buy from their initial shortlist. If you’re not on it, no amount of sales effort will save you.

🔍 So, what’s the playbook for modern marketing? Kerry explains why demand creation—not just demand capture—is the key to winning future deals. Marketers must move beyond gated content, outbound cadences, and “hunting” leads. Instead, they need to build brand presence early, engage in buyer communities, and ensure their company is top-of-mind long before a purchase is in motion.

Key Takeaways:

✅ Only 1-3% of your ICP is in-market at any given time. Most SaaS companies waste time on buyers who simply aren’t ready.
✅ Buyers ignore cold outreach until they decide to engage. 50% receive calls and emails for weeks (even months) before responding.
✅ Analysts and consultants influence over 80% of SaaS deals. If analyst relations aren’t part of your strategy, you’re missing a major growth lever.

💡 The companies winning today aren’t chasing buyers—they’re positioning themselves as the obvious choice before a buying cycle even starts. Kerry shares how 6Sense does this and how your team can apply these insights to future-proof your marketing.

🎧 Listen now to learn how to shift your strategy for today’s B2B buyer.

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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: Maxwell Nee, CRO at ScoreApp

Maxwell 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.

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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 Group

In 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:

1. 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.
2. Messaging Is No Longer Durable: Static messaging fails in today’s dynamic market. Iterative testing ensures campaigns stay relevant and effective.
3. 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

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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: Steve Brothers, CEO of Splashmetrics

With 77% of millennial buyers avoiding sales interactions until they’ve already made a purchase decision, buyers are consistently clear about what they need: fast, personalized, and self-directed answers. 

Yet vendors stubbornly stick to outdated practices, forcing buyers into their processes rather than meeting them where they are.

In this episode of SaaS Backwards, Steve Brothers, CEO of Splashmetrics, explores how modern B2B buyers are reshaping the sales process—and how many vendors are failing to adapt. 

He discusses how Splashmetrics bridges this gap by enabling companies to deliver tailored, interactive content journeys that put buyers in control while providing sales with critical insights to close deals more effectively.

Key Takeaways:

1. The buyer is in control: Buyers prefer to self-educate, completing 80% of their research before engaging with sales. Vendors must adapt or risk irrelevance.
2. Outdated models kill opportunities: Relying on traditional MQL-driven processes results in 95% of SDR outreach being ignored.
3. TheSplashmetrics solution: The platform allows buyers to “choose their own adventure,” and bridges the sales-marketing divide to create a truly buyer-centric experience.

This episode is a wake-up call for companies still stuck in yesterday’s playbook.

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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.