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 strateg...
Jun 27, 2025•38 min•Season 4Ep. 23
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 falli...
Jun 13, 2025•25 min•Season 4Ep. 22
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...
May 30, 2025•33 min•Season 4Ep. 21
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 , no...
May 23, 2025•37 min•Season 4Ep. 20
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 enviro...
May 16, 2025•42 min•Season 4Ep. 19
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 pow...
May 09, 2025•32 min•Season 4Ep. 18
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...
May 02, 2025•49 min•Season 4Ep. 17
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 ...
Apr 25, 2025•47 min•Season 4Ep. 16
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-m...
Apr 17, 2025•34 min•Season 4Ep. 15
Guest: James D. Wilton, Founder & Managing Partner of Monevate The advent of AI is forcing a complete rethink of traditional SaaS pricing—particularly the long-standing dominance of user-based pricing. In this episode, pricing strategist James Wilton explains why AI-native products are undermining the foundations of per-seat pricing models. Unlike traditional SaaS, where users are the proxy for value, AI tools often perform tasks autonomously, disconnecting cost from usage in unpredictable w...
Apr 11, 2025•36 min•Season 4Ep. 14
Guests: Ken Lempit, James Ollerenshaw, & Rob Curtis AI is transforming SaaS—but not in the way most leaders think. Forget the headlines claiming "SaaS is dead." The real shift isn't just in tools—it's in how fast software is built, marketed, and bought. In this episode, Rob Curtis (VC-backed founder), Ken Lempit (SaaS GTM strategist), and James Ollerenshaw (AI advisor) break down what AI means for the future of SaaS—and why B2B CROs and CMOs need to rethink their strategy now or risk falling...
Apr 04, 2025•39 min•Season 4Ep. 13
Guest: Guy Rubin, Founder & CEO at Ebsta Most 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 &...
Mar 28, 2025•32 min•Season 4Ep. 12
Guest: Srikrishnan Ganesan, Co-Founder & CEO of Rocketlane Most 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 fr...
Mar 14, 2025•32 min•Season 4Ep. 11
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 movin...
Mar 07, 2025•28 min•Season 4Ep. 10
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 noi...
Feb 28, 2025•37 min•Season 4Ep. 9
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 mistak...
Feb 21, 2025•34 min•Season 4Ep. 8
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 lev...
Feb 14, 2025•29 min•Season 4Ep. 7
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. ...
Feb 07, 2025•29 min•Season 4Ep. 6
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, ...
Jan 31, 2025•38 min•Season 4Ep. 5
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 concep...
Jan 24, 2025•32 min•Season 4Ep. 4
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, ena...
Jan 17, 2025•32 min•Season 4Ep. 3
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 ...
Jan 10, 2025•29 min•Season 4Ep. 2
Guest: Beth McHugh, Fractional Product Leader When deals stall, buying committees often default to doing nothing. Why? Because they didn’t all agree that the problem was worth solving. In this episode, Beth McHugh explains why pain points alone rarely drive action and how the Jobs to Be Done (JTBD) methodology identifies the “struggling moments” that compel prospects to move forward. These critical moments are when a prospect or team collectively decides that a problem can no longer be ignored. ...
Jan 03, 2025•32 min•Season 4Ep. 1
Guest: Bob Moesta, Author of “Demand-Side Sales 101” In this episode, Bob Moesta, author of Demand-Side Sales 101 , reveals why uncovering your customers’ “struggling moments” is the single most efficient step for any business. Whether it’s product development, marketing, or sales, understanding the root causes behind why customers make a change transforms every decision you make. As Bob explains, customers don’t buy products—they hire solutions to make progress. Without a clear struggling momen...
Dec 20, 2024•35 min•Season 3Ep. 47
Guest: Peter Cohan, Author of “Great Demo!” Have you ever walked into a software demo, hoping to learn something new, only to sit through a “Harbor Tour” of irrelevant features? You’re not alone – and neither are your prospects. Peter Cohan, author of Great Demo! , joined us on the SaaS Backwards Podcast to unpack the biggest demo mistakes SaaS teams make: ❌ Starting with the how instead of the why ❌ Overloading prospects with unnecessary features ❌ Failing to tailor demos to decision-makers His...
Dec 13, 2024•36 min•Season 3Ep. 46
Guest: Randy Likas, Head of North America Go-to-Market at Nektar Traditional marketing tactics are losing their edge, with MQLs falling short as costly, outdated signals of real buyer intent. In this week’s episode, we explore tactics for CROs to tackle the “great ignore” with guest Randy Likas, Head of North America Go-to-Market at Nektar , a revenue efficiency platform that unifies customer interaction data and helps you discover new revenue opportunities. Randy discusses how CROs must reevalu...
Dec 06, 2024•31 min•Season 3Ep. 45
Guest: Isabelle Papoulias, Fractional GTM & Business Operations Executive Pipeline isn't just a metric—it's a team sport. But when marketing, sales and customer success work in silos, it creates a fractured buyer journey and practically guarantees you’ll miss opportunities. So, who should be responsible for driving this cross-functional alignment? In this episode, fractional GTM leader and business operations executive Isabelle Papoulias breaks down how SaaS companies can realign their go-to...
Nov 27, 2024•29 min•Season 3Ep. 44
Guest: Warren Zenna, Founder of The CRO Collective Scaling a SaaS company is no walk in the park. At a certain point, operational complexity demands more than just growth—it demands cross-functional alignment. Enter the Chief Revenue Officer (CRO). In this episode, we dive into the evolving role of the CRO with expert Warren Zenna, founder of The CRO Collective and Zenna Consulting Group , and host of the CRO Spotlight podcast. Warren unpacks why misalignment between Sales, Marketing, and Custom...
Nov 22, 2024•34 min•Season 3Ep. 43
Pricing and packaging can either bog down your go-to-market engine or fuel it to peak performance. This week’s SaaS Backwards podcast features Dan Balcauski, Founder and Chief Pricing Officer at Product Tranquility , a consultancy that helps high-volume B2B SaaS CEOs define pricing and packaging for new products. In this episode, Dan discusses the critical role pricing plays in a SaaS business model and why leadership teams must view it as a dynamic lever, not a "set-it-and-forget-it" element. H...
Nov 15, 2024•40 min•Season 3Ep. 42
Gifting can be a powerful outbound strategy that captures attention far more effectively than an email. In this week’s SaaS Backwards podcast episode, we spoke with Kris Rudeegraap, Co-CEO and Co-Founder at Sendoso , a gifting and direct mail platform that helps revenue teams 6x second call rates, double win rates, and close deals 29% faster. Kris shared how his background in software sales and experience with gifting inspired him to create Sendoso. He provided insights into the company’s initia...
Nov 08, 2024•22 min•Season 3Ep. 41
