This episode was recorded prior to Teresa Anania’s move to Chief Customer Officer at Verint. At the time of recording, she was SVP of Customer Experience at Sophos.Teresa Anania (CCO at Verint, formerly CCO at Sophos) joins GTMnow to share how she's built customer success into a true revenue engine at a company serving 600,000 customers across over $1 billion in annual revenue, and why the old reactive, relationship-based CS model is no longer cutting it.At Sophos, the threat landscape is compounding fast. AI is accelerating the speed and sophistication of attacks, which means response times, customer journeys, and success motions all have to evolve in lockstep in order to keep up. Teresa has spent her career at companies like Zendesk, Autodesk, and ON24 building the operational frameworks that make that possible at scale.Mentioned Resources: Cleverbridge: Merchant of Record for Software & SaaS​Guest links: Teresa Anania - LinkedIn: https://www.linkedin.com/in/teresa-anania/Sophos - LinkedIn: https://www.linkedin.com/company/sophos/Sophos - Website: https://www.sophos.com/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X (Twitter):

Jason Demant just joined GTMfund as Partner, Head of Networks after 6 years at Foundation Capital where he reviewed over 1,000 emerging manager funds and invested in 100+.In this episode, Max (GP), Paul (GP), and Jason break down what separates the VC firms that survive from the ones that quietly die, why the best founders today are skipping mega funds at pre-seed, and what LPs are excited in about emerging managers.What we cover:The real reason raising from mega funds at pre-seed can backfireWhy less than 10% of VC firms ever make it to Fund 3What makes an emerging manager fundable (sourcing, founder support, durability)The media flywheel that gives certain funds an unfair advantageHow LPs should think about mega funds vs. emerging platforms (the barbell approach)Why founders are the ones now choosing their investors, not the other way aroundConnect with Jason: / jasondemant Connect with Max: / maxaltschuler Connect with Paul: / paulsirving GTMnow is the media extension of GTMfund, a venture capital firm investing in early-stage B2B companies. Every episode features operators, investors, and founders on the front lines of go-to-market.Timestamps:

NEW: @Paul Fipps (President of Global Customer Operations at @ServiceNow) joins GTMnow to break down how ServiceNow built the customer engine behind $10B+ in revenue and 20%+ growth for five consecutive years.From CIO at Under Armour overseeing a 300 million-member connected fitness ecosystem, to now leading global sales, customer success, field marketing, and partners at one of the most disciplined GTM organizations in enterprise software, Paul has seen what it takes to scale from both sides of the table.In this conversation, you'll learn:- Why complacency is a bigger threat than competition at scale- How to detect churn long before it shows up in a report- What a CIO cancelling 900 AI pilots tells you about where enterprise AI is actually headed- How ServiceNow unified sales, customer success, field marketing, and partners into one GTM motion so customers never feel the org chart- Why ServiceNow monitors customer health daily — and what signals their teams actually track- How community became a core GTM advantage, not just a marketing channel- How ServiceNow’s AI Control Tower governs agents across the enterprise stack- Inside “Now on Now”: how ServiceNow generated $335M in annualized AI productivity gains using its own platform- How integrating Claude into the GTM workflow cut account planning from days to minutes- What DTC product thinking from Under Armour unlocked in enterprise GTM- How ServiceNow shifted from 6-month product releases to monthly innovation cycles- Paul’s advice for building a world-class GTM organization: put the best people in the right seatsGuest links: Guest - LinkedIn: https://www.linkedin.com/in/paulfipps/Guest company - LinkedIn: https://www.linkedin.com/company/servicenow/Guest company website: https://www.servicenow.com/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X (Twitter):

Brett Queener (Partner at Bonfire Ventures) joins GTMnow to share what three decades across Siebel, early Salesforce, co-founding, and seed-stage investing has taught him about what actually wins now that software is cheaper and faster than he ever imagined.Brett was one of the earliest GTM hires at Salesforce when it had seven employees. He helped build the go-to-market playbook that defined a generation of SaaS: enterprise segmentation, sales motion design, product marketing, the whole works. He then co-founded SmartRecruiters, angel invested in companies like Outreach and Pando, and eventually joined Bonfire Ventures as a Partner to do early-stage investing the way he thinks it should be done: hands-on, operator-led, and built around founders who are ruthless about execution.Guest links:Brett Queener - LinkedIn: https://www.linkedin.com/in/brettqueener/Bonfire Ventures - LinkedIn: https://www.linkedin.com/company/bonfire-ventures/Guest company website: https://www.bonfirevc.com/Host links:Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/Max - X: https://x.com/HackItMaxPaul - LinkedIn: https://www.linkedin.com/in/paulsirving/Paul - X: https://x.com/PaulGTMNewsletter: https://thegtmnewsletter.substack.comBrought to you by: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale wit

Dan Wright (Co-founder & CEO of Armada) joins GTMnow to unpack what it actually takes to bring AI infrastructure to the places the cloud was never built to reach.The cloud covers about 30% of the world. The other 70% (think: oil rigs, the Arctic tundra, military ships, remote mines) is where some of the most critical decisions happen, making latency a life-or-death and billions of dollars difference. Armada is building the infrastructure for that part of the world: modular, ruggedized AI data centers that go to the data, instead of the other way around.From the first offshore edge computing deployment with the US Navy, to cutting avalanche response times in Alaska from over a day to real time, to sovereign AI installations in Saudi Arabia with Aramco and Microsoft, Armada is redefining what operating at the edge even means.In this episode, we cover:- Why cloud infrastructure was built for a pre-AI world and what that gap costs- How Starlink turned every remote location into a potential AI cluster- What "distributed intelligence" means and why it's the founding principle behind Armada- The global race for AI sovereignty and why modular compute is the linchpin- How Armada goes to market when a product demo involves shipping a 40-foot container to a desert (yes, really)- Why customer champions are better than any sales rep- The Microsoft partnership and how Armada extends Azure to places Azure could never go on its own- Category creation lessons from building a company before the market had a name for the industry- What's next: SpaceX, sovereign AI, and why Dan thinks humans are on the moon in two years (yes, REALLY)Guest links: Dan Wright - LinkedIn: https://www.linkedin.com/in/wrightdh/, hDan Wright - X: https://x.com/danwrightSFArmada - LinkedIn: https://www.linkedin.com/company/armadaai/Armada - Website: 

NEW: @Sheila Vashee (CMO of @Figma) joins GTMnow to share how she thinks about brand building across every stage. From selling brownies at age eight, to second marketing hire at Dropbox scaling to $1B+ in annualized revenue, to now leading marketing at one of the most beloved software brands in the world, Sheila has seen it all.In this conversation, you’ll learn what brand actually means (hint: it's not your logo), how PLG companies make the leap to enterprise, why being obsessively close to your customers is a compounding advantage, and how AI is reshaping the marketing playbook without replacing the human craft that sets great brands apart.Guest links:- Guest - LinkedIn: https://www.linkedin.com/in/sheilavashee/ - Guest company - LinkedIn: https://www.linkedin.com/company/figma/- Guest company website: https://www.figma.com/Host links:- Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/- Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona- Newsletter: https://thegtmnewsletter.substack.comSponsors: - HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at

Bill Binch (Operating Partner at Battery Ventures) joins GTMnow to share the operational frameworks he's built across 116 quarters on quota, and what actually changes when you move from driving revenue to advising an entire portfolio.Before Battery, Bill was employee #16 at Marketo, where he led sales from zero revenue through IPO and a Vista Equity acquisition. He then served as CRO at Pendo, helping scale ARR to nearly $100M in only three years. His career spans some of the most defining sales organizations in enterprise software, from Oracle to PeopleSoft.- Bill Binch - LinkedIn: https://www.linkedin.com/in/bill-binch-302a4a2/, - Battery Ventures - LinkedIn: https://www.linkedin.com/company/battery-ventures/- Battery Ventures website: https://www.battery.com/Host links:- Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/- Max - X: https://x.com/HackItMax- Paul - LinkedIn: https://www.linkedin.com/in/paulsirving/- Paul - X: https://x.com/PaulGTM- Newsletter: https://thegtmnewsletter.substack.comBrought to you by: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure

Dan Lee (Co-Founder & CEO of Nooks) joins GTMnow to give a behind the scenes on how Nooks is launching a new Agent Workspace and AI Sequencing layer designed to operate across the full action set of a rep’s day — calls, emails, research, prospecting, and strategy.The conversation explores why top of funnel is changing the fastest, why traditional sequencing tools optimize the “move” but not the strategy, and how AI systems that learn from rep behavior can compound advantage over time. As adoption deepens, automation can move from ~40% of outbound execution toward 70% and beyond, while switching away resets that intelligence.We also discuss the broader category shift: customers pushing AI-native tools to take on incumbents, the rise of agent workspaces as the new interface for GTM teams, and why calls remain the most data-rich channel in outbound compared to silent email non-responses.Guest links: Guest - LinkedIn: https://www.linkedin.com/in/dan9lee/Guest company - LinkedIn: https://www.linkedin.com/company/nooksapp/Guest company website: https://www.nooks.ai/Host links:Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Sophie Buonassisi - X (Twitter): https://x.com/sophiebuonaNewsletter:

Emir Atli (Co-founder and CRO of HockeyStack) joins GTMnow to share how go-to-market is shifting in the AI era — from fragmented tools and GTM sprawl to unified, AI-native platforms built on a single data foundation.Originally known for attribution and market intelligence, HockeyStack is evolving into a central operating system for go-to-market, spanning marketing, sales, and post-sales through AI agents, blueprints, and an execution layer.We also explore weekly GTM sprints, founder-led content as a pipeline driver (even with <100 followers), and the long-game mindset behind building a generational company from age 20 after YC.In this episode, we cover:- Why you can’t layer AI onto legacy GTM — you must rebuild GTM around AI- The “sprawl crisis” and why siloed tools break without a single data foundation- HockeyStack’s evolution from attribution to a unified GTM operating system- AI agents, blueprints, and the shift from reporting to execution- Why consolidation is moving from tools to full buyer journey control- The case for a winner-takes-all GTM platform- How AI increases leverage across reps, managers, and pipeline reviews- Weekly GTM sprints and faster iteration cycles in the AI era- Founder-led content as a core growth engine and pipeline driver- LinkedIn as a top channel for MQL-to-opportunity and deal acceleration- The 10-year mindset, YC lessons, and building a generational companyGuest links: Emir Atli - LinkedIn: https://www.linkedin.com/in/emiratli/- HockeyStack - Website: https://www.hockeystack.com/- HockeyStack - LinkedIn: https://www.linkedin.com/company/hockeystack/Host links:- Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/- Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona- Newsletter: https://theg

Amanda “Robby” Robson (Founder of Modern Technical Fund) joins GTMnow to break down how she evaluates companies at the very earliest stages and why discipline matters more than ever in today’s market.Amanda has spent over a decade in venture before launching Modern Technical Fund, investing across verticals ranging from security and compliance to developer tools at firms like Norwest and Cowboy Ventures. Her investment thesis is centered on backing elite technical founders early and helping them translate deep engineering talent into real products, real customers, and real momentum.In this conversation, we unpack how Amanda thinks about founder quality, market timing, and risk when there’s limited data and plenty of noise, which is more critical than ever in an AI-heavy investing environment.Guest LinksAmanda’s LinkedIn: https://www.linkedin.com/in/amanda-robson-7227685b/Amanda’s Twitter: https://x.com/robby_mtfModern Technical Fund’s LinkedIn: https://www.linkedin.com/company/modern-technical-fund/Modern Technical Fund website: https://moderntechnicalfund.com/Host links: Max - LinkedIn: https://www.linkedin.com/in/maxaltschuler/Max - X: https://x.com/HackItMaxPaul - LinkedIn: https://www.linkedin.com/in/paulsirving/Paul - X: https://x.com/PaulGTMNewsletter:

Archana Agrawal (President of Intercom) joins GTMnow to share how Intercom (founded in 2011) successfully restructured its product, pricing, and go-to-market to become AI-native at a speed and scale most legacy SaaS companies haven’t achieved.Their agent, Fin, now handles 80%+ of support volume, resolves 1M customer issues per week, and has grown from $1M to $100M+ ARR with a $0.99 outcome-based pricing model backed by up to a $1M performance guarantee if resolution targets aren’t met.In this episode, we cover:- Why customer support is fundamentally a 24/7 business- How Fin now handles 80%+ of customer queries through automation- Why human empathy often breaks down in real-world support workflows- How AI makes instant, individualized service possible for the first time- Why Intercom put a million-dollar guarantee behind its resolution rate- What it takes to confidently price software on outcomes- Why the future of support is humans + AIGuest links: - Archana Agrawal - LinkedIn: https://www.linkedin.com/in/archana-agrawal/- Intercom - LinkedIn: https://www.linkedin.com/company/intercom/- Intercom’s Fin Agent: https://fin.ai/Host links:- Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/- Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona- Newsletter:

Lou Shipley (three-time CEO, Harvard Business School professor, and author of Unlikely Entrepreneurs) joins GTMnow to break down why most founders struggle to turn good ideas into great companies.Lou has led companies through acquisitions, teaches sales and go-to-market at Harvard, and has spent decades studying what actually separates companies that scale from those that stall.In this conversation, we unpack why understanding customer pain and learning how to sell are still the two most important founder skills, especially as product moats decline and go-to-market becomes the real differentiator.In this episode, we discuss:- Why understanding customer pain matters more than having a great idea- Why early selling should optimize for learning, not revenue- Why founders can’t outsource sales too early- How distribution becomes a competitive advantage at scale- What makes “unlikely entrepreneurs” outperform expectations- Why small, high-quality teams beat large organizations- Why churn is a symptom, not the root problem- How product-market fit quietly changes as companies grow- Why founders must evolve from heroic sellers to system builders- How culture becomes a real go-to-market assetLou also shares lessons from teaching sales at Harvard, profiling 13 unlikely entrepreneurs, and working with founders who realized too late that they were building the wrong company for the wrong customer.If you’re a founder, operator, or investor trying to avoid costly early mistakes and build a company that actually scales, this episode will give you a clearer mental model for what matters most.Timestamps:00:00 – What actually makes a company great00:26 – Why early selling is about learning, not revenue01:47 – Why founders misunderstand customer pain02:06 – “If you build it, they will come” is a lie02:33 – Distribution as the real moat02:58 – What makes an “unlikely entrepreneur” succeed06:15 – Why age and experience increase founder success07:01 – Curiosity, coachability, and risk eliminatio

Healey Cypher (multi-time founder and CEO of BoomPop) joins GTMnow to unpack one of the fastest growing channels for company growth: in-person events.As AI floods digital channels with perfectly personalized messages, trust is becoming harder to earn online. Healey explains why events, dinners, and in-person experiences are becoming a premium GTM channel, not a nice-to-have, and how founders can use them intentionally for distribution, alignment, and acquisition.In this episode, we discuss:- Why in-person events are becoming a premium GTM channel in an AI-first world- How founders can de-risk distribution before building the product- The most common internal missteps that derail startups early- Why offsites are the new HQ for remote and hybrid teams- How to design offsites that drive alignment, not just fun- What makes a dinner actually work — including overlooked details like acoustics- How teams use events for customer acquisition and partnerships- Why kindness and positivity can be a real leadership advantageHealey also shares a powerful insight from Sam Altman that reframes how we should think about AI’s impact on trust and human connection.If you’re interested in scaling events as a growth channel, this episode will give you all the details you need and an understanding of what is working in today’s world.Timestamps:00:00 – Why founders underestimate distribution03:30 – Product vs distribution: what actually matters early06:45 – Why most startups fail from internal misalignment10:30 – Culture, communication, and focus as scaling constraints14:40 – Hybrid work broke alignment17:45 – Why offsites are becoming the new HQ21:30 – Events as a go-to-market strategy25:00 – AI, outbound fatigue, and inbox trust collapse28:40 – “In-person experiences are becoming a premium”32:30 – How to use events for customer and partner acquisition36:15 – What makes a high-impact event vs a wasted one39:50 – Dinners, summits, and unforgettable experiences43:30 – Leadership, kindness

Why do so many go-to-market motions fall apart right when a company starts to scale?In this episode of GTMnow, Sophie Buonassisi sits down with Jeanne DeWitt Grosser, former GTM leader at Google and Stripe and now COO at Vercel, to unpack why GTM fragility is one of the most underdiagnosed risks in startups and scaling companies.This is a deep, operator-level conversation about what actually breaks in sales, why AI won’t magically fix it, and how the best teams treat go-to-market like a product that must be designed, tested, and iterated.If you are a founder, operator, or investor navigating growth, this episode will give you clearer mental models for building GTM that actually holds up under pressure.In this episode, we cover:Why most GTM motions fail at scale, even with strong productsWhat it really means to treat go-to-market like a productHow AI changes execution without changing fundamentalsThe rise of the forward deployed engineerWhy “lost on price” is usually a lieWhat great sales reps still do better than anyone in the AI eraHow to think about joining companies “early” without getting timing wrongListen if GTM feels fragile, unpredictable, or overly dependent on heroes.Timestamps00:00 – Introduction01:00 – “Yes is great. No is great. Maybe will kill you.”02:00 – Why go-to-market should be treated like a product04:45 – Designing the experience of being sold to06:30 – Using AI to debug GTM process failures09:00 – Why “lost on price” usually isn’t about price12:00 – What go-to-market engineering actually is16:00 – The rise of the forward deployed engineer20:45 – AI, agents, and what still needs human judgment25:45 – What great sales reps do differently in the AI era29:30 – Why GTM roles are becoming more consultative33:30 – Will there be an AI reckoning?38:00 – What “joining early” really means42:00 – Career lessons from Google, Stripe, and Vercel44:00 – Closing thoughts

Mark Goldberg is a Managing Partner and Co-Founder at Chemistry, a new early-stage venture firm with a $350M debut fund backing standout software companies from Seed to Series A. Prior to Chemistry, Mark was a Partner at Index Ventures, where he led early-stage investments across software and fintech for nearly a decade. Before Index, Mark was one of the first business hires at Dropbox, helping the company navigate hypergrowth. Discussed in this episodeWhy Mark studied international relations, and why venture feels like “the liberal arts of jobs”Index’s US “invisibility” era and what that taught him about building a new firmThe Chemistry spinout thesis: “take great multi-stage DNA, reconstitute it with focus”Fund design: pre-seed → seed → A, light reserves, and concentrated doubling-downHiring strategy: network access > spreadsheet diligenceCulture principles: excellence, performance, “no one takes themselves too seriously”Conviction-based investing vs consensus IC, and why omissions are the real killerThe hardest lesson in venture: managing co-founder dynamics (and when to just listen)Episode highlights00:00 — “A+ people want to work with A+ people.”01:46 — GTMfund’s 2026 prediction: big players come roaring back (Google, Meta, Microsoft, Uber/Waymo).14:51 — GTMfund platform metrics: thousands of support items, intros, hires, and fundraising connects.26:29 — Why Mark left Index to build Chemistry: big-fund lessons, rebuilt with focus.33:39 — Chemistry’s strategy: early-stage focus, light reserves, and building for “product-market discovery.”44:05 — “Venture doesn’t scale well.” Why Chemistry stays small to avoid bureaucracy.49:59 — Events that actually work: chess tournaments, surfing, and hobby-driven gathering > happy hours.54:56 — Investment process: conviction, not consensus—optimize for outliers, not averages.1:10:32 — Hardest lesson in venture: co-founder dynamics, and learning when to listen (not “advise”).Brought to you by: AngelListFrom starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificin

Abbas Haider Ali is SVP of Customer Success at GitHub, where he leads a 550+ person post-sales organization supporting a $2B+ ARR business serving over 150 million developers, including more than 90% of the Fortune 100.Previously, Abbas was VP of Customer & Partner Success at Twilio following its acquisition of Segment, and has held executive roles at xMatters, Opnet Technologies, Managed Objects, and IBM. He is also a General Partner at GTM Operators Network, investing from seed through growth, and is deeply committed to mentorship and advancing underrepresented leaders in tech.Discussed in this episode:Why “AI-led growth” can hide churn and value erosionLagging vs leading indicators for retention enduranceWhy the CS investment benchmark is shifting from 10% → ~7%A simple “waterfall” for allocating post-sales budget: support → onboarding → outcomesHow to “lever up” the envelope with premium support + professional servicesWhy expansion (not renewals) is the early signal of product-market fitThe rise of AI-powered specialized generalists in post-salesWhen forward deployed engineers make sense (and when they’re just a fad)Episode highlights00:00 — Why customer expansion is the real signal of product-market fit00:50 — Lagging revenue vs. leading indicators of endurance04:11 — Why the CS benchmark dropped from 10% to 7%08:41 — How AI moved from internal efficiency to customer-facing leverage11:41 — Why retention cost matters more than CAC in the AI era14:17 — The simplest framework for allocating the 7% CS budget18:53 — Founder-led CS, design partners, and early-stage PMF myths23:16 — The rise of AI-powered specialized generalists30:00 — When forward-deployed engineers actually make sense49:31 — The one rule for building a durable SaaS companyThis episode is brought to you by our sponsor: HockeyStackIf you run go-to-market, you already know the problem: your data lives everywhere. Spreadsheets, CRMs, sales calls, ad platforms… yet you’re still guessing what to do next.HockeyStack is the AI platform for modern GTM teams. It unifies all your sales and marketing data into a single system of action. Built-in AI agents help teams prospect the right accounts, improve conversions, close and ex

Adam Carr is the Chief Revenue Officer at Apollo, where he’s scaling revenue by layering sales on top of a $150M+ ARR product-led growth engine. Previously, Adam helped scale Miro from a PLG-led company into a global sales organization, contributing to its growth into a $17.5B business. He’s known for building systems-driven GTM teams that turn product signals into durable revenue.Discussed in this episodeWhy PLG is gravity (signals + acquisition) and sales is the monetization layerThe “one-team” model to prevent PLG vs. sales cannibalizationBuilding talent density (and why slowing hiring can be the fastest path)Hiring for curiosity, coachability, ownership, and team-first executionThe “architect / systems thinker” profile for modern sellersA new post-sales model: CSMs → technical GTM Engineers + intervention-led journeyUsing customer journey milestones to drive expansion and prevent churn proactivelyAI in GTM: streamlining manual work so humans focus on better conversationsEpisode highlights00:00 — PLG is about signaling + acquisition (not monetization)01:30 — “PLG isn’t the monetization way… it’s layering sales.”02:41 — Talent density: hire for the next 12–18 months, not just “today”04:50 — The soft skills that scaled Miro: curiosity, coachability, ownership08:38 — Why Adam hires “architects” (system thinkers) instead of just sellers10:41 — The mindset shift: celebrate value realized, not contracts signed15:41 — Replacing CSMs with “go-to-market engineers” + an intervention model19:14 — Turning PLG signals into PQA/PQL routing (and reducing the “noise”)29:26 — “100M ARR is late” — when to start layering sales into PLGGuest linksLinkedIn (Adam Carr):https://www.linkedin.com/in/adamhcarrFollow Sophie Buonassisi (Host)LinkedIn: https://www.linkedin.com/in/sophiebuonassisiX (Twitter): https://x.com/sophiebuonaNewsletter: https://thegtmnewsletter.substack.comWhere to Find GTMnowWebsite:

Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage firm in New York backing category-defining SaaS, fintech, and vertical software companies. Before investing, she spent 15 years as a GTM operator, serving as Chief Revenue Officer at Sailthru and later Chief Customer & Commercial Officer at Marigold (Campaign Monitor, Sailthru, and other martech brands), where she scaled global sales, marketing, and customer success organizations.Today, Cassie leads investments while also running Primary’s Impact program, giving founders access to a 30-person team across talent, GTM, and strategic finance, and she continues to teach operators through programs like Pavilion and Duke’s Innovation & Entrepreneurship board.Discussed in this episode:How Cassie “accidentally” became a VC after 15 years in GTM leadership.The career advice Bill Gurley gave her that changed her trajectory.Why Primary refuses to say “platform” and instead built a 30-person Impact team.How she actually sources pre-seed/seed founders before they leave their jobs.Primary’s 5-part Founder Outcomes Framework (vision, talent, JDCE, and more).The difference between real traction vs. “happy ears” and fake design partners.Why she’s picky on GTM/AI tools and looks for step-change, not incremental gains.How operators can actually break into VC (hint: it’s all about doing the work).Episode highlights00:35 — Clay, usage-based pricing, and the $100M ARR rocketship09:10 — The real story on AISDR: where AI reps actually work (and where they really don’t)14:02 — Inside “The Gross Retention Apocalypse” and why AI experimental budgets are a ticking time bomb22:46 — How Cassie accidentally became a VC and the Bill Gurley advice that changed her career path27:17 — Why Primary hates the word “platform” and how Cassie built a 30-person Impact team for founders36:10 — Cassie breaks down her 5-part founder outcomes framework (including “jaw-dropping customer experience”)46:01 — Avoiding “happy ears”: how founders should really use design partners and MedPick-style rigor57:48 — Time to value as the new north star and why nailing a tight wedge beats peanut-buttering features1:01:29 — So you want to be a VC: Cassie’s playbook for operators to bre

Dave Boyce is a go-to-market–focused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, he’s helped founders navigate the shift from sales-led to product-led, from gut-driven to instrumented, and now from manual GTM to AI-assisted systems. Today, Dave teaches revenue architecture and PLG through Winning by Design’s Growth Institute, works with leadership teams on Bow Tie–based growth models, and is all-in on how AI will reshape GTM as a true engineered system.Discussed in this episodeWhy classic sales & marketing playbooks haven’t caught up to how modern buyers actually buy.How the Bowtie model exposes the real levers of growth that funnels hide.Why PLG-style thinking is now essential even for sales-led and enterprise motions.The 3 first principles of freemium: empathy, generosity, and metrics.Where AI can reliably outperform humans across the customer journey, and where it absolutely shouldn’t.How to design hybrid human + AI workflows using a clear data model, not vibes.What RevOps should own in a modern revenue architecture (and why it can’t just serve the CRO narrative).Hard-earned founder lessons from Fundly on reinvention, calling bets early, and letting go of old branches.Episode highlights00:00 — GTM is still running 20-year-old playbooks01:29 — “Sales, marketing, CS… the last unengineered engine”03:20 — The myth of “just add more heads”05:50 — The Fundly story: reinvention, too late08:30 — Why Freemium had to be written11:01 — Three first principles of freemium15:25 — Mapping AI across the entire customer journey19:29 — “Automate the predictable, humanize the exceptional”25:18 — What the Bowtie exposes that funnels hide27:25 — Building a “minimum viable BowtieThis episode is brought to you by our sponsor: ZoomInfoZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in compet

Brian Weinberger is the Chief Revenue Officer at Sisense, a leading analytics platform helping companies embed intelligence into every product experience. With over 30 years in sales leadership across New York’s tech scene, Brian has built and scaled go-to-market teams at every stage—from early-stage startups to category-defining giants like Yext, Segment, and Salesforce.Discussed in this episodeThe evolution of partner selling — from VARs to SIs to ecosystemsHow to know if partner selling fits your GTM modelThe delivery-first mindset that drives retentionDirect vs. partner motion: Microsoft vs. SalesforceWhy enablement is the #1 green flag for partner successPartner marketing: how to make resellers self-sustainingUsing AI to power future-ready GTM modelsThe case for hybrid work in high-performance sales culturesEpisode Highlights00:00 — The “year four” moment when partners are selling for you01:07 — 30 years of selling through partners in New York03:22 — Start partner strategy with delivery, not distribution06:32 — Why partner selling creates “superhuman” sellers09:59 — Salesforce vs. Microsoft: direct vs. reseller — and why the future is hybrid12:13 — The startup hack: sell delivery on your paper, subcontract partners17:16 — A 90-day playbook for integration partnerships21:39 — Hiring the right people to build a partner business27:18 — How Sisense runs delivery partners and an Australian reseller29:55 — White-labeling Snowflake: using resell to get the giant’s attentionThis episode is brought to you by our sponsor: BoomPopWe’re deep in event planning right now, as no doubt many of you are.Whether it’s an offsite, conference, or any other kind of event, BoomPop makes that happen with end-to-end planning all in one place.They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.Follow Brian WeinbergerLinkedIn: