GTM by the Numbers

Benchmarkit Podcast Network
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Nov 4, 2025 • 53min

Ep 11: The New Rules of Pricing, Packaging and Monetizing in the Age of AI with Marcos Rivera

In this episode of GTM By the Numbers, host Brandon Redlinger sits down with Marcos Rivera, Founder of Pricing I/O and author of Street Pricing, to unpack the radically shifting world of SaaS and AI pricing models. Marcos has helped hundreds of tech companies—from startups to scaled platforms—navigate monetization strategy, and in this conversation, he shares practical insights on how to stay profitable in the new AI economy.Marcos breaks down why SaaS pricing playbooks no longer work for AI-native products, and why leaders must rethink how they measure value, define margins, and build customer trust. He introduces new frameworks like BAM (Base, Allowance, Meter) and REAL (Revenue, Expense, Avoidance, and Lift), and outlines exactly how to price and package AI tools in ways that drive real adoption and protect long-term revenue.What you’ll hear in this episode:The biggest mistakes leaders make when monetizing AIWhy “wishful ARR” is screwing up GTM forecastingHow to structure hybrid pricing models using BAMWhy value attribution is a team sport (not just marketing’s job)The new risk-adjusted ROI mindset investors are demandingWhen to underscore, upgrade, or unlock your AI productWhat most people misunderstand about usage-based pricingWhy lazy SaaS is dead—and how AI is forcing teams to up their gameIf you're navigating GTM strategy in an AI-influenced world, this episode is essential listening.Connect with Marcos on LinkedIn at linkedin.com/in/marcoslrivera/Connect with Brandon on LinkedIn at linkedin.com/in/brandonredlingerSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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8 snips
Oct 21, 2025 • 45min

Ep 10: The State of AI in Go-To-Market: What’s Working, What’s Not & What To Do About It with Kristina McMillan

Kristina McMillan, a pioneering force in go-to-market strategies and a leader at Scale Venture Partners, dives into the current state of AI in GTM. She discusses the leading roles of marketing and sales development in AI adoption, while customer success lags. Kristina highlights the shift from basic AI applications to more strategic uses, the importance of go-to-market engineers, and how to effectively measure AI impact with new benchmarks. She also shares insights on effective change management and the future of AI in making better decisions.
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Oct 8, 2025 • 49min

Ep 9: How to Make Brand Your Growth Engine in the Age of AI with Anthony Kennada

In this episode of GTM by the Numbers, host Brandon Redlinger chats with Anthony Kennada, former CMO at Gainsight, Hopin and Front. He has now turned CEO and held that position at AudiencePlus and currently at Goldenhour. Anthony shares a radical rethink of what it means to build brand in the age of AI. While many B2B companies still treat brand as fluff, Anthony argues it's the last true differentiator. In a world where features can be copied and campaigns automated, emotional connection and human experience become strategic levers.From orchestrating the unforgettable Pulse conferences at Gainsight to launching the audience-first GTM playbook at Audience Plus, Anthony breaks down how brand, content, and events come together to drive real revenue outcomes.What you’ll learn in this episode:Why 80% of traditional marketing will be automated, and what’s left for humans to ownThe 3 pillars of "Brand Humanity" and why every company needs to start hereHow to build audience before product (and why it leads to better launches)What most companies get wrong about category creationWhy the CEO (not the CMO) is the true owner of brandHow to activate emotional connection at scale (even in enterprise GTM)A framework for building internal alignment around brand-led initiativesWhen events are worth the budget, and when they’re notIf you’re a founder, CMO, or marketing leader wrestling with how to differentiate in a noisy, AI-saturated world, this episode offers clarity, conviction, and a blueprint for brand-led growth.Connect with Anthony on LinkedIn linkedin.com/in/akennadaConnect with Brandon on LinkedIn at linkedin.com/in/brandonredlingerSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Sep 23, 2025 • 44min

Ep 8: The Hard Truth About Going Up-Market (and Why Most Teams Fail) From Karl Ortmann's Revenue Problem Solvers Podcast

In this special episode of GTM by the Numbers, we’re flipping the script. Instead of hosting a guest, we’re rerunning Brandon Redlinger’s appearance on the Revenue Problem Solvers podcast with host Karl Ortmanns.The conversation centers on one of the toughest GTM challenges out there: moving up-market. Brandon shares battle-tested stories from his time leading marketing at high-growth SaaS companies, including both painful lessons and breakthrough wins when transitioning from mid-market to enterprise.You’ll hear why a single big logo isn’t proof of readiness, how to align product, marketing, and success teams for enterprise buyers, and why hiring experienced talent in the right vertical can make or break your motion.What you’ll learn in this episode:– Why closing one big account doesn’t mean you’re “enterprise”– How to know when it’s actually the right time to move up-market– The critical role of product readiness and customer success in scaling to enterprise– Why focus beats chasing every vertical, and how Brandon found success with healthcare– The importance of hiring for expertise instead of retraining your best mid-market sellersThis is a must-listen for GTM leaders eyeing larger deals and wondering what it really takes to scale successfully.Connect with Karl Ortmanns at https://www.linkedin.com/in/karlortmanns/Connect with Brandon at linkedin.com/in/brandonredlingerSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Sep 9, 2025 • 51min

Ep 7: Building Media Brands Inside B2B SaaS and the Future of Content Strategy with Kathleen Booth

In this episode of GTM by the Numbers, host Brandon Redlinger chats with Kathleen Booth, SVP of Marketing & Growth at Pavilion, about the evolution of GTM strategy through the lens of media. Kathleen shares why she’s betting big on building an owned audience, how Pavilion is treating its media brand as a standalone subsidiary, and why YouTube could be the next frontier for B2B content.They dive into the metrics that actually matter when running a media-first GTM play, the differences between broad-based versus niche podcast distribution, and the challenges of proving out audience growth to CEOs who want fast results.What you’ll hear in this episode:Why owning your audience is the ultimate GTM moatHow Pavilion is experimenting with YouTube for audience growthThe KPIs Kathleen is tracking to measure media ROIWhy different podcast formats succeed on different platformsThe tension between leadership expectations and actual GTM executionIf you’ve been wondering whether your GTM strategy should look more like a media strategy, this episode will give you both the frameworks and the inspiration to start.Resources mentioned in this episode:Pavilion: The world's #1 private community for GTM leaders https://www.joinpavilion.com/TopLine Podcast: Pavilion’s podcast that is being used as a pilot for YouTube audience growth.https://www.joinpavilion.com/topline-podcastKyle Norton: CRO of Owner.com (and past guest on Ep 2 of GTM by the Numbers). Mentioned in context of other Pavilion podcasts.https://www.joinpavilion.com/the-revenue-leadership-podcasthttps://youtu.be/xWwDW4WLFz0?feature=sharedSaaS Talk with Ray Rike and Dave Kellogg: A podcast that provides practical strategies and metrics for improving B2B SaaS companies' revenue growthhttps://www.benchmarkit.ai/saas-talkGTM Summit: industry event both Brandon and Kathleen planned to attend. https://attendgtm.com/Connect with Kathleen on LinkedIn: https://www.linkedin.com/in/kathleenslatterybooth/Connect with Brandon on linkedin.com/in/brandonredlingerSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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15 snips
Aug 26, 2025 • 51min

Ep 6: The Language of the Boardroom: P&L Fluency and Reading the Market with Cassie Young

Cassie Young, General Partner at Primary Venture Partners, shares her unique insights as a former SaaS operator turned investor. She discusses why P&L fluency is crucial for aspiring C-suite leaders and offers tips to strengthen partnerships with CFOs. Cassie also dives into the importance of speed as a competitive advantage in the AI age, the impending renaissance of customer success, and how GTM leaders can maintain a market pulse by listening to customers. Her stories from career turnarounds are peppered with actionable advice for today’s fast-paced SaaS landscape.
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Aug 12, 2025 • 53min

Ep 5: Reimagining Marketing and Team Structure in the Age of AI: What's Working and What's Not with Jon Miller

In this episode of GTM by the Numbers, Brandon Redlinger chats with Jon Miller to rethink how marketing and revenue teams should operate when AI is at the core—not bolted on. Jon breaks down where AI is already working (inbound agents, agentic workflows that compress prep/follow-up) and where it isn’t (spray-and-pray outbound “personalization” without human oversight). He explains why to avoid multi-year vendor lock-in during this transition, how “AI-curated playlists” will replace rigid nurture streams, the emerging shape of GTM orgs (fewer SDR bodies, rise of GTM engineers), and how to measure AI’s impact through efficiency and effectiveness with pipeline and revenue still as the gate.In this episode, we break down:Why bolting AI onto 15–25-year-old, rules-based systems is “lipstick on a pig”, and what it looks like when reasoning replaces rules.The “AI DJ” model: 1:1 orchestration that curates a personalized playlist of actions for every contact (goodbye, one-size-fits-all nurtures).Agentic AE workflows that auto-build account plans, research, and follow-ups so reps spend less time prepping and more time selling.AI SDRs: why inbound agents shine (speed + always-up-to-date) and why outbound still needs real human oversight.Measuring AI with hard ROI on efficiency (time saved) vs. harder-to-measure effectiveness (synthetic panels, engagement lift, pipeline).How AI will disintermediate your marketing (search today, inbox tomorrow) and what survives (experiences, relationships and craftsmanship)Resources mentioned in this episode:Claude (Anthropic): Jon and Brandon reference using Claude for building and experimenting with AI workflows and prototypes.https://www.anthropic.com/claude Lovable: “Vibe-coding” tool Jon and Brandon discuss for quickly prototyping apps/sites to convey product vision.https://lovable.dev/ Clay + HubSpot integration: Used by Brandon to automate research, notes, and follow-ups in GTM workflows.https://www.clay.com/university/guide/hubspot-integration-overview All-In Podcast: One of Jon’s go-to listens to understand diverse viewpoints.https://allin.com/ Christopher S. Penn / Trust Insights: Jon’s recommended source for staying current on marketing AI.https://www.trustinsights.ai/blog/ From Impossible to Inevitable (Aaron Ross & Jason Lemkin): Quoted during the selling-time discussion.https://fromimpossible.com/ Connect with Jon at LinkedIn: https://www.linkedin.com/in/jonmiller2Connect with Brandon at linkedin.com/in/brandonredlingerSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Jul 29, 2025 • 57min

Ep 4: Why Most GTM Efficiency Metrics Are Dead Wrong And What CROs Should Track Instead with Jacco van der Kooij

In this episode of GTM by the Numbers, host Brandon Redlinger chats with Jacco van der Kooij, founder of Winning by Design, to unpack why most GTM efficiency metrics are dead wrong—and what CROs should be tracking instead. They dive into the Bow Tie model, the rising cost of acquisition, and the untapped power of customer-led growth. If you're leading a SaaS revenue team and questioning whether your metrics actually reflect success, this conversation will give you the clarity, and the playbook, you need.What you’ll hear in this episode:Why most SaaS GTM teams are addicted to acquisitionHow to calculate GTM efficiency and what "good" really looks likeThe impact of operational debt on growthHow to create customer-led campaigns that scaleWhy post-sale motions are underfunded (and how to fix it)When expansion should drive more growth than acquisitionWhy modern sales trips should feel like “Lollapaloozas”The rise of HLG (Human-Led Growth) and what to do about itResources mentioned in this episode: Winning by Design AI – “Talk to Jack”: An AI-powered assistant on the Winning by Design site that answers GTM questions and includes hidden “Easter eggs” for curious users.Link: https://www.winningbydesign.com/aiPavilion: A community platform for reps and leaders to leverage for peer-based networking and customer engagement during sales trips.Link: https://bit.ly/pavilion-membershipDavid Spitz Reports on SaaS GTM Efficiency: Mentioned as a leading source for analyzing GTM efficiency across public SaaS companies, especially in relation to CAC trends.Link: https://benchsights.com/Connect with JaccoLinkedIn: https://www.linkedin.com/in/jaccovanderkooij/Winning By Design: https://winningbydesign.com/Connect with BrandonLinkedIn: linkedin.com/in/brandonredlingerSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Jul 15, 2025 • 47min

Ep 3: Attribution Myths, Brand Truths & Capital-Efficient Growth with Bill Macaitis

In this episode of GTM by the Numbers, host Brandon Redlinger sits down with Bill Macaitis—the former CMO who propelled Salesforce, Zendesk, and Slack to breakout growth and now advises the next generation of SaaS disruptors through SaaS CMO Pro. Together they unpack what it really takes to build a capital-efficient, customer-obsessed GTM engine in 2025.Bill explains why traditional last-touch attribution is broken, how to prove marketing impact with control-group experiments, and the mindset shifts every GTM leader needs in an AI-driven world. They also dive into aligning incentives across marketing, sales, and product, the underrated power of NPS, and why brand is the ultimate growth lever when budgets tighten. If you’re a GTM executive aiming to scale fast without burning cash, this conversation is a must-listen.What you’ll learn in this episodeThe fatal flaws in common attribution models, and how AI-powered regression analysis fixes themHow to design low-cost control groups (city, segment, or account) that finally silence board-room skepticismWhy Bill tracks NPS and post-sale CSAT alongside pipeline targetsA practical framework for unifying marketing, sales, and product around shared revenue metricsThe comp-plan adjustments that stop channel infighting and start collective quota-crushingWhere AI is taking attribution next—and how to future-proof your RevOps stackHow to build a lovable B2B brand that fuels word-of-mouth and lowers CACConnect with BillLinkedIn: linkedin.com/in/bmacaitisSaaS CMO Pro: saascmopro.comConnect with BrandonLinkedIn: linkedin.com/in/brandonredlingerSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Jul 2, 2025 • 58min

Ep 2: Building a Metrics-Obsessed Revenue Operating System That Scales with Kyle Norton

In this episode of GTM By the Numbers, host Brandon Redlinger sits down with Kyle Norton, CRO of Owner.com and host of the Revenue Leadership Podcast, to unpack what it truly takes to lead a high-performing, metrics-driven GTM org. Known for his obsession with operational rigor and data fluency, Kyle breaks down his Revenue Operating System. Kyle explains he builds dashboards, forecasts with precision, and trains frontline leaders to make data-backed decisions.They also explore the CRO’s real job (hint: it’s not just hitting a number), how to prevent your team from gaming inputs, and why the best GTM leaders think like systems engineers and behavioral psychologists. If you’re a revenue leader who wants to scale with speed and sustainability, this episode is a must-listen.What you’ll learn in this episode:Why most CROs misunderstand what VCs actually valueHow Kyle structures daily dashboards and BI tools for clarity, not chaosThe behavioral psychology behind “breadcrumb selling”The metric he uses instead of activity volume to assess SDRsHow to build data literacy into frontline managersThe real ROI of investing in post-sale ops and onboardingWhy great GTM leaders think in systems, not just quotasSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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