SaaS Backwards - Reverse Engineering SaaS Success

Guest: Ray Meiring, Co-Founder & CEO at QorusDocs

Scaling a SaaS business from consultancy roots to enterprise success requires more than just great tech—it takes ruthless focus, smart go-to-market choices, and a deep understanding of your buyer.

In this episode, Ray Meiring, co-founder and CEO of QorusDocs, joins host Ken Lempit to share the lessons learned on his journey from South Africa to the U.S. market and how QorusDocs carved out a winning niche in AI-powered proposal automation.

We unpack:
 ✅ Why founder-led sales can’t scale—and how to move beyond it
 ✅ The trap of chasing SMBs after funding (and what to do instead)
 ✅ How QorusDocs found product-market fit through one anchor customer
 ✅ What every SaaS CRO and CMO should know about RFP response teams
 ✅ The critical role of marketing in driving pipeline (not just sales)

Ray also shares the moment venture funding pushed them off course—and how doubling down on their ideal customer profile helped them reset, rebuild, and grow more efficiently.

If you're a SaaS CMO or CRO scaling into enterprise, navigating founder-to-function transitions, or wondering where AI really moves the needle, this episode is packed with firsthand insight.

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Guest: Sammy Greenwall, Founder of Henry.ai

What if your go-to-market motion could skip past theory and build from real-world pain?

That’s exactly how Sammy Greenwall, founder of Henry.ai, approaches commercial real estate—and why his vertical AI startup is scaling without traditional sales or marketing. 

Sammy’s background as a CRE professional-turned-founder gave him not only insight, but language, trust, and distribution advantages. In this episode, he shares how founder-market fit drives everything from product strategy to GTM efficiency—and how it’s paying off in a space historically allergic to software.

Sammy also pulls back the curtain on:

• How PLG became a byproduct of customer obsession—not the plan
• Building a waitlist-worthy brand (with no ad budget)
• Creating real enterprise value in a low-trust, high-volume industry

Three Key Takeaways for B2B GTM Leaders:

1. Founder-Market Fit > Generic Product-Market Fit
Sammy’s deep domain experience gave him a faster path to traction: he didn’t just “identify” pain—he lived it. That meant smarter onboarding flows, tighter feature prioritization, and messaging that clicked with buyers the first time. CEOs and founders with industry-specific experience should lean hard into that unfair advantage.

2. PLG Isn’t a Tactic—It’s the Outcome of Product Obsession
Henry.ai didn’t set out to be a PLG company. Instead, they tracked usage down to individual clicks, met with every early user, and iterated daily. That intensity created a product people wanted to talk about, which fueled organic adoption, referrals, and even early enterprise wins.

3. AI Doesn’t Just Accelerate Work—It Replaces It
In CRE, Sammy’s platform cut multi-week deal deck creation down to hours. That kind of workflow disruption isn’t about “boosting productivity”—it’s about letting revenue-generating staff focus on high-value activities like deals and relationships. This shift reframes AI adoption for skeptical buyers and opens the door to premium pricing.

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And the best part?

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Guests: Ken Rapp (Co-Founder & CEO) and Emily Lagasse (VP of Marketing) of Bluestream

What if the key to SaaS growth isn’t more leads, but fewer customer drop-offs post-purchase?

In this episode of SaaS Backwards, we sit down with Ken Rapp (Co-founder & CEO) and Emily Lagasse (VP of Marketing) of Blustream, the platform pioneering post-sale engagement, to explore how product ownership experiences are unlocking revenue, retention, and lifetime value.

According to Rapp and Lagasse, most brands obsess over acquisition, but lose up to 70% of customers before the second purchase. Blustream flips that script by transforming post-purchase silence into an intelligent, AI-powered dialogue that guides customers through onboarding, usage, care, and reordering.

Key takeaways include:

📦 Unboxing is a retention opportunity
🤖 AI predicts drop-off and upsell moments
🛠️ Don’t launch on platforms too early
🎯 Vertical focus beats “sell to everyone”

If you’re a SaaS CRO or CMO looking to drive net revenue retention, boost repeat purchases, or reimagine how post-sale moments can be monetized, this episode is for you.

🔗 Blustream Journey Builder

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And the best part?

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Guest: Casey Woo, CEO & Founder of Operators Guild & FOG Ventures

What happens when startups are built not by armies of specialists, but by lean teams of senior generalists paired with AI agents?

In this episode of SaaS Backwards, we sit down with Casey Woo—CEO and Founder of FOG Ventures and the Operators Guild—to explore how AI is transforming the fundamental structure of companies. 

According to Woo, the org chart of the future isn’t just flatter and faster—it’s hybrid, where strategic, multi-discipline humans lead and AI agents handle executional work once done by junior staff.

From finance and support to engineering and ops, AI is hollowing out the middle, forcing leaders to become broader, sharper, and more cross-functional. 

Think “Special Forces” over traditional departments. The operators who thrive will be the ones who can think horizontally, move fast, and execute across domains.

Other key insights from the episode include:

• 🪖 Why early-stage startups need “scalers”—T-shaped operators who do a little of everything—to survive guerrilla warfare, not corporate specialists trained for big wars.
• 💥 The rise of roles like COFO (Chief Operating + Financial Officer) as titles and functions blend in response to new business demands.
• 🚀 A framework for understanding when to bootstrap vs. raise VC—and why many founders get it wrong by ignoring ROI and lifestyle trade-offs.
• 🌍 How Casey accidentally grew the Operators Guild into a 1,200+ member global force, and why its culture of “give more than you get” is key to its explosive success.

If you want to understand what the next wave of high-performance SaaS companies will look like—and who will build them—this conversation is essential.

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Your messaging could be turning buyers away before you even get a chance to pitch.

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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: Google’s NotebookLM

In this special episode of SaaS Backwards, we handed the mic to AI.

We took our newest ebook on reviving inbound marketing—coming soon for download—and ran it through Google’s NotebookLM to see what kind of podcast it could generate. 

The result? A surprisingly sharp—if occasionally cheesy—take on how B2B SaaS companies can reimagine their go-to-market strategies for today’s buyer. You be the judge.

The episode explores why the traditional inbound playbook is falling short and what CROs and CMOs must do to adapt. From the collapse of predictable revenue models to the rise of buyer-centric marketing, we break down how to align sales and marketing, test messaging organically, and coordinate campaigns across email, ads, and outreach.

Key Takeaways:

• The old predictable revenue model no longer works in today’s B2B SaaS landscape
• Buyers now do deep independent research before ever talking to sales
• Marketing and sales alignment must happen before the formal buying process begins
• Jobs to Be Done and qualitative ICPs help create relevance and resonance
• Organic testing (especially on LinkedIn) is essential before scaling paid campaigns
• Email, ads, and SDR outreach must be tightly coordinated around buyer triggers

If you’re a SaaS leader looking to modernize your inbound strategy and connect with today’s buyer, this episode offers a bold, practical roadmap—created by AI, guided by strategy.

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And the best part?

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No commitments, no pressure—just actionable advice to help you book more demos.

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Guest: Eli Portnoy, Founder & CEO at BackEngine

As B2B SaaS companies scale, they often lose touch with the customers who got them there.

In this episode, Eli Portnoy, founder and CEO of BackEngine, sits down with Ken Lempit to talk about the critical breakdown in customer feedback systems—and how generative AI can help leaders hear what really matters.

We unpack:
✅ Why customer feedback loops break as SaaS companies grow
✅ The hidden costs of misaligned feedback channels and weak ownership
✅ How AI can synthesize 100% of customer interactions—without surveys
✅ What separates elite SaaS companies from the rest when it comes to NRR and churn
✅ Why CS leaders are uniquely positioned to become strategic feedback owners

Eli also shares the story of losing his biggest customer before a major fundraise—and the moment he realized feedback was everyone’s problem, but no one’s job.

If you're a CMO, CRO, or CS leader building a feedback-driven growth engine, this is a conversation you won’t want to miss.

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And the best part?

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Guest: Ayse Guvencer, Fractional SaaS CMO & GTM Executive

As AI changes how B2B buyers evaluate software, many marketers are missing the forest for the trees.

In this episode, Ayse Guvencer, fractional CMO and GTM advisor to SaaS and MarTech startups, joins Ken Lempit to deliver a blunt reality check: AI is disrupting the search journey, pricing models, and even how buyers interact with your brand—before your SDRs even know they exist.

We unpack:

 ✅ Why Google is now a navigational tool, not a discovery engine
✅ How AI-driven tools like ChatGPT are shaping shortlists and decision frameworks
✅ The rise of Generative Engine Optimization (GEO) and what it means for visibility
✅ Why “Service as a Software” is redefining outcome-based pricing
✅ What AI browsers and agentic advertising could mean for reaching the “hidden figures” on buying committees

Ayse also shares practical guidance on how marketers can stay ahead of AI-native competitors, avoid falling for adtech black boxes, and reframe their role in this fast-changing ecosystem.

If you’re a B2B SaaS CMO or CRO trying to stay ahead of the curve, this is one of those episodes you’ll want to listen to twice.

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Guest: Jim Curry, CoFounder at BuildGroup

Is AI really transforming your SaaS business—or just adding noise?

In this week’s episode, Jim Curry, co-founder of BuildGroup and former Rackspace exec, discusses how AI is transforming both the products and operations of SaaS businesses—and why most companies are missing the opportunity.

Jim shares how BuildGroup's operator-first, long-term approach to investing gives them an edge when helping SaaS companies scale, especially in today’s AI-first environment. He explains why AI should be seen as an infrastructure wave (not just a flashy product feature), and how CROs and CMOs can practically apply it to go-to-market execution.

We cover:

• Why AI gives incumbents an advantage (if they act fast)
• How to use AI to reduce CAC and improve GTM speed
• Where traditional SaaS GTM playbooks break down in an AI-native world
• Why demos and SDR workflows are ripe for automation
• How BuildGroup partners deeply with founders post-investment

If you're a SaaS executive thinking about where to apply AI for real impact—without waiting for a full replatform—this conversation is packed with insight.

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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.

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Guest: Ken Lempit, President & Chief Business Builder at Austin Lawrence Group

Are your SaaS ads actually doing their job, or just burning budget?

In this week’s episode of SaaS Backwards, Ken Lempit and Jason Myers of Austin Lawrence Group go deep on what GTM leaders get wrong about advertising in 2025:

• Why most SaaS ads look and sound the same (and fall flat)
• Where messaging fails long before the click
• How to align sales and marketing in a high-consideration buying cycle
• The overlooked power of direct mail and live events
• When to pull back on spend—and how to know it’s time

If you’re spending more but converting less—or just tired of “safe” campaigns with no spark—this conversation will challenge your assumptions and give you a new 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.