SaaS Backwards - Reverse Engineering SaaS Success

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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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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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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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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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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Guests: Ken Lempit, James Ollerenshaw, and Rob Curtis

Voice is the new frontier in SaaS — but are we ready for the implications?

In the third episode of our AI Series, Ken Lempit is joined again by James Ollerenshaw and Rob Curtis to explore how voice and AI are colliding to transform the way B2B SaaS companies operate — from the way products are built and sold to how customers are supported.

We dive into:

• The shift to voice-first interfaces and its implications for product design
• Real-world use cases in sales, customer service, compliance, and manufacturing
• Why voice as a data source may be more valuable than voice as an interface
• How voice AI can unlock productivity gains — and which roles are at risk
• The compliance, privacy, and cultural risks of voice-powered surveillance
• Predictions on headless SaaS, ambient computing, and the next big AI disruption

This conversation goes longer than our typical episodes, but trust us — it’s worth every minute. Stick around for smart insights, practical frameworks, and some provocative predictions that CROs, CMOs, and SaaS builders shouldn’t miss.

📢 Learn more about Rob’s venture at standuphiro.com
🧠 Connect with Ken at austinlawrence.com

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Guests: Ken Lempit, James Ollerenshaw, and Rob Curtis

AI isn’t just a bolt-on anymore—it’s rewriting the rules of SaaS from the ground up.

In this episode, Standup Hiro co-founder Rob Curtis and tech strategist James Ollerenshaw join host and GTM expert Ken Lempit to unpack how Agentic AI is forcing SaaS leaders to rethink everything: product design, go-to-market, customer trust, and even internal culture.

From natural language interfaces to the rise of AI “co-workers,” they break down why SaaS companies that adapt will dominate—and why bolt-on AI features won't be enough to survive.

📌 Key Takeaways:

• The Age of AI Co-Workers
  Forget copilots. The next SaaS revolution will be about true AI teammates—systems that work with you, not just for you.
• Natural Language is the New UI
  SaaS buyers are expecting to talk, not click. Voice-first experiences and conversational commands will soon be table stakes.
• Trust Is the New Battlefield
  Enterprises are more forgiving of human errors than machine mistakes. To win with AI, SaaS leaders must prove not just capability, but reliability.
• Bolt-Ons vs. Reinvention
  Tacking AI onto legacy products won’t cut it. Companies willing to re-architect around AI-native principles will seize the biggest opportunities.
• Invisible Software is Coming
  Many SaaS tools will fade into the background, powering workflows behind the scenes. The battle for customer love (and margin) starts now.

Heads up: This episode runs longer than usual—but for good reason.
We go deep into the real-world implications of Agentic AI, from product strategy to pricing models, trust, and the future of SaaS UX. If you're a SaaS leader trying to stay ahead of the AI curve, every minute is packed with actionable insights that could reshape how you build, sell, and scale.

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And the best part?

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Guest: Sjoerd Handgraaf, Chief Marketing Officer at Sharetribe

The most overlooked growth lever in SaaS? Positioning.

In this episode, Sharetribe CMO Sjoerd Handgraaf reveals how redefining product positioning transformed their trajectory—and why many SaaS companies are still getting it wrong.

Handgraaf takes us inside Sharetribe’s journey from chasing big logos to doubling down on their true customer: non-technical marketplace founders. Along the way, he shares hard-won insights about product-market fit, AI disruption, and why going “back to basics” in marketing may be more transformational than the next tech trend.

📌 Key Takeaways:

• The Power of Saying No
  Why Sharetribe walks away from enterprise deals—and how that clarity unlocked faster product development, happier customers, and less internal chaos.
• Product-Market Fit is a Moving Target
  What feels like “fit” today can vanish tomorrow. Sjoerd explains why it's not a one-time milestone, but a constant process of adaptation.
• The AI Threat is Real—but Misunderstood
  Low-code and AI-assisted development may lower technical barriers, but they don’t replace the need for reliability, support, and fit-for-purpose tools.
• Content Marketing That Converts
  Sharetribe’s global growth is powered by giving first—through books, podcasts, and resources that attract high-intent buyers before they’re even in-market.
• Global from Day One
  How to build a self-serve SaaS product that scales globally—even from a startup hub like Finland.

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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.