GTM 167: Competing with Giants: Inside You.com’s Battle Against OpenAI & Google | Peter Grant
Peter Grant is the Chief Revenue Officer at You.com, the AI search and productivity platform reshaping how people find and create information. A veteran GTM leader, Peter has built and scaled revenue engines at some of tech’s most iconic companies — from Siebel Systems to Salesforce to C3.ai — working directly under legends like Tom Siebel and Marc Benioff. Today, he’s leading You.com’s charge against giants like OpenAI and Google, bringing precision, storytelling, and speed to the most transformative era in technology.Discussed in this episodeHow Peter defines “the biggest opportunity of our lifetime” in AILessons from working under Tom Siebel, Marc Benioff, and Rishi KhoslaHow to hire SEAL-Team-Six-level GTM talentWhy belief and speed are non-negotiables when competing with giantsYou.com’s differentiation strategy against OpenAI and GoogleHow to operationalize AI literacy and agentic workflowsThe ROI gap in generative AI adoption, and how to fix itBuilding products that stand on truthEpisode Highlights00:14 — The biggest opportunity in technology this century05:25 — Lessons from working directly with Thomas Siebel06:41 — How to hire “SEAL Team Six” sales talent10:24 — Why “train hard, fight easy” defines great enablement20:08 — The new sophistication bar for AI literacy in sales25:14 — How You.com differentiates against OpenAI & Google30:00 — Peter’s personal AI productivity system: 40 agents40:12 — Speed, truth, and trust: You.com’s go-to-market culture48:30 — The “war room” story: building a sales plan overnight59:45 — No easy days: why startup life mirrors special forcesThis episode is brought to you by our sponsor: BoomPopA quick pause to spotlight a partner that helps GTM teams actually connect—BoomPop.Your next big unlock might not come from another meeting… it’s from getting your team in the same room. BoomPop makes that happen with end-to-end offsite 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.And as a listener of GTMfund, you’re eligible for full-service event planning for just $99 per person (terms apply).Head to boompop.com/gtmfund to start planning your offsite.Guest LinksLinkedIn: linkedin.com/in/peterkgrantCompany: you.comRecommended BooksThe Hard Thing About Hard Things by Ben HorowitzElephants Can’t Dance by Louis V. Gerstner Jr.The Master Algorithm by Pedro DomingosNo Easy Day by Mark Owen — a favorite for its lessons on grit and resilienceThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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The GTMnow Podcast Bonus: ‘I joined Meta at 900, left at 90,000’ — Rick Kelley on Building and Scaling International Sales Teams
This bonus episode dives into how Rick Kelley helped scale Meta’s global sales organization (from 900 employees to 90,000) and the playbook behind building high-performing international teams.Rick Kelley is the former SVP of Gaming and App Monetization Solutions at Meta and Managing Director of Meta Ireland, where he led a $1B+ revenue organization and played a pivotal role in building out Meta’s go-to-market teams across North America and EMEA. Over his 15-year career at Meta, Rick was instrumental in driving international expansion, especially across Europe, the Middle East, and Africa—helping to localize strategy, scale high-performing sales teams, and bring new ad products to market. Today, he advises founders on global GTM execution, sales hiring, and how AI is reshaping the future of commercial organizations.This is a clip from the full episode with Rick, an inside look at how Meta built its $1B EMEA business and the lessons every GTM leader can apply to scale globally.Discussed in This Clip:The exact framework Rick used to decide which EMEA markets to enter firstHow Meta built a $1B+ regional business from just three salespeopleThe power of centralization in early-stage go-to-marketWhy you should plan every headcount allocation before hiringCreating “optionality” in your sales org to weather changeHow gaming became Meta’s fifth global regionWhen to localize sales teams versus staying centralizedWhy AI can make sales more efficient—but can’t replace relationshipsHighlights00:12 — Scaling Meta: from 900 to 90,000 employees01:22 — How Rick Kelley built Meta’s mid-market sales org from scratch02:15 — The data-driven framework Meta used to prioritize global markets04:50 — Why startups should build expansion plans before executing07:52 — Centralized vs. in-country hiring: Rick’s take for startups09:49 — The importance of sales ops and forecasting discipline13:32 — Hiring leaders who scale with you, not limit you14:59 — How AI will reshape (but not replace) sales relationships16:09 — From zero to $1B: lessons in efficiency, cost, and cultureThis Episode Is Brought to You ByZoomInfo 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 competitive markets.It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.Learn more at zoominfo.com.Follow Rick KelleyLinkedIn:https://www.linkedin.com/in/rickkelley/The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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GTM 166: SEO → AEO: The Next Big Shift in How People Discover Your Product
Guy Yalif is Chief Evangelist at Webflow and a veteran B2B marketing leader with 20+ years across Twitter, Yahoo, BrightRoll, and as co-founder/CEO of Intellimize (acquired by Webflow). He champions AI-driven optimization for sites and content, bringing a rare blend of aerospace-engineer rigor and operator experience from four successful exits to help teams win the shift from SEO to AEO.Discussed in this episodeWhy AEO is an evolution of SEO (and what truly changes)The shift from keywords to “clusters of questions” as the new topic modelWebflow’s four-part AEO framework: content, technical, authority, measurementTactics that moved the needle: adding FAQs + schema; prioritizing freshnessWhy PR/brand and plain-text mentions matter more to AI enginesHow to measure AEO: presence in questions, share of voice, and sentimentWhere to start: two moves any founder can ship this weekRisks of ignoring AEO and the early-adopter advantageEpisode highlights00:21 — “Your SEO resources are your AEO resources. This is an evolution, not a reset.”01:15 — Webflow’s AEO promise: answer engines are a massive arbitrage—akin to early SEO/SEM/mobile.03:00 — Why “ranking for keywords” is obsolete; topics = clusters of questions across the funnel.07:49 — The 4-part AEO framework: content, technical (schema & structure), authority, measurement.10:11 — Case study: Add ~6 FAQs + inline schema to product pages → half of new citations came from 6 pages; +24% organic in 2 weeks.15:23 — If you only do two things: (1) answer questions comprehensively, (2) add schema metadata.21:46 — Webflow data: AI-search traffic converts ~6x better than non-branded organic; unbranded share grew from 0% → 42% in a year.24:02 — How buyers actually use LLMs in-flow; why your website still matters (to humans and machines).29:58 — The learning curve is back: why AEO is resetting the playing field and rewarding curiosity.This episode is brought to you by our sponsor:ZoomInfo 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 competitive markets.It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.Learn more at zoominfo.com.Follow Guy Yalif:LinkedIn: https://www.linkedin.com/in/gyalif/X (Twitter): https://x.com/gyalifX (formerly Twitter)Webflow author page: https://webflow.com/people/guy-yalifThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
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GTM 165: Vibe prompting, AI fluency, and the new rules of go-to-market | Kieran Flanagan
Kieran Flanagan is the SVP of Marketing at HubSpot and Co-Host of Marketing Against the Grain. A longtime operator and investor, he’s at the forefront of how AI is reshaping go-to-market. With a background in engineering and years leading growth and marketing teams, Kieran now spends his time building, experimenting, and sharing lessons on how prompting, agents, and personality-led growth will define the next era of software companies.Discussed in this episodeWhy prompting and context engineering are the most important skills for GTM operatorsHow “vibe prompting” accelerates learning and output with LLMsThe three keys to building AI fluency inside teamsMeasuring ROI from AI across sales, marketing, and operationsWhy every professional is now a manager (of AI agents)How websites will evolve into multimodal closing mechanismsThe rise of personality-led growth in B2B marketingWhy curiosity and persistence matter more than ever in an AI-first worldEpisode highlights00:46 — The 100x difference between good and bad prompting03:57 — The rise of “context engineering” as a GTM skill07:22 — Kieran’s 3-part framework for AI fluency inside teams09:31 — Why “vibe prompting” is as powerful as vibe coding11:00 — How AI boosts conversions & deal velocity in sales workflows15:10 — Using ChatGPT memory as a personalized prompting coach22:19 — Everyone now manages a PhD-level AI intern31:12 — The 3 biggest shifts coming to GTM: influence, AI optimization, multimodal37:42 — Why AI makes human creativity more valuable than ever43:06 — The grind, reps, and curiosity as the ultimate AI skillsBrought to you by: MutinyAre you a B2B Marketer running campaigns for target accounts? Then you know the struggle: tedious and manual processes, endless delays to get things live, and sales feeling like you’re not doing enough.That’s where Mutiny comes in. Mutiny is the fastest place to launch breakthrough campaigns for your target accounts. AI agents research your accounts, build personalized landing pages, and scale everything from LinkedIn ads to sales handoffs, all in one seamless workflow. No more stitching tools together. Just smarter, more impactful campaigns powered by real data. Launch in days, not weeks.See why teams who use Mutiny generate 3X more account engagement.Book a demo at mutinyhq.comGuest linksLinkedIn: https://www.linkedin.com/in/kieranjflanagan/Newsletter (The AI Marketing Generalist):https://www.kieranflanagan.io/Podcast (Marketing Against the Grain):https://www.youtube.com/@MATGpod/videosHost linksLinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X (Twitter): https://x.com/sophiebuona Newsletter: https://thegtmnewsletter.substack.com/ Website: https://gtmnow.comThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where she’s applying her experience building high-velocity GTM engines to the next generation of developer-first tools.Discussed in this episodeWhy Cristina joined Stripe without knowing what an API wasBuilding Stripe’s early partnerships and salvaging the Shopify dealHow Notion pioneered community-driven growthLessons on brand, design, and investing for the long termWhat Cristina looks for in exceptional founders and operatorsHow Linear is scaling GTM with AI-driven prioritizationThe difference between “keeping the lights on” and transformative leadershipCristina’s frameworks for evaluating product resonance and customer loveEpisode Highlights00:43 — The rare superpower behind Cristina’s career: joining breakout companies early2:46 — Why Cristina joined Stripe without knowing what an API was12:22 — On Cristina’s first day, Shopify walked away from Stripe’s deal — and how she won them back16:55 — How Notion scaled by making consumer use free and fueling community-driven growth20:52 — Why investing in brand early is a leading indicator of durable growth25:27 — Cristina’s framework for spotting beloved products in the market37:53 — How Cristina applied lessons from Stripe to build Linear’s GTM from scratch47:30 — Where AI fits into GTM: prioritizing opportunities, not replacing humans56:01 — Why Linear built high-quality swag kits for early customers58:28 — Where to follow Cristina’s journey todayThis episode is brought to you by our sponsorHarmonic helps you discover the best startups way ahead of the competition. We use it at GTMfund, as do thousands of investors at firms like USV and Insight. GTM teams at companies like Notion and Brex also rely on the platform to stay ahead.Harmonic tracks millions of startups and lets you search using simple filters or natural language to match exactly what you’re looking for. When you find a company that looks interesting, Harmonic pulls everything into one place (founder backgrounds, traction, and market data) so you can quickly evaluate and understand if it’s a fit.At GTMfund, we even have a private Slack channel called #companywatchlist powered entirely by Harmonic.Get 2 dedicated sessions with their team to help you test and structure the perfect searches here.Guest LinksLinkedIn: https://www.linkedin.com/in/cristinajcordovaX (Twitter): https://x.com/cjCThe GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.
The GTMnow Podcast interviews well-known tech executive, VC, and founders - the expert operators in the trenches who have ‘been there, done that’ to build some of the fastest-growing software companies. Every week, a guest joins Sophie Buonassisi to dissect their stories, revealing expert insights around what worked, what didn’t, and how things actually went down.This podcast is produced by GTMnow, the media brand of GTMfund - sharing insight on go-to-market from working with hundreds of portfolio companies backed by over 350 of the best go-to-market executives. GTMfund is an early-stage VC fund focused on investing in the most exciting, up-and-coming B2B SaaS companies across the world. The LP network consists of VP and C-level Sales, Marketing, and Customer Success leaders from companies like DocuSign, Salesforce, LinkedIn, Snowflake, Okta, Zoom, and many more.Visit gtmnow.com for more details and to sign up for our newsletter and other content resources.
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