The GTMshift

Jordan Crawford builds an outbound campaign live on stage, using Claude Code to go from a raw market to qualified prospects with a personalized reason to reach out. He crawls tens of thousands of company sites, mines case studies for named champions, finds who's since changed jobs, and pulls it all together into a message worth replying to. Before the build he pulls apart a few AI outbound attempts that missed, making his case for starting from imagination and cheap per-prospect intelligence instead of the same old filters.Follow Jordan: https://www.linkedin.com/in/jordancrawford/Follow James: https://www.linkedin.com/in/jameskaikis/Read more from GTMshift: https://gtmshift.substack.com/---The AI-Fluent Revenue Leader was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_aifluentrevGradient: https://bit.ly/GradientVentures-aifluentrevCaptivate Talent: https://bit.ly/CaptivateTalent-aifluentrevClarify: https://bit.ly/Clarify-aifluentrevClay: https://bit.ly/Clay-aifluentrevOutworks: https://bit.ly/Outworks-aifluentrev

Elaine Zelby, founder and CRO of Tofu, breaks down how she's using AI to build pipeline at Tofu. She starts by grounding her ICP in real CRM and call data, then layers signal-based agents on top that watch for the compelling events that actually turn an account into a live deal. She gets into why win rates jump inside a true ICP fit, the buying signals worth acting on, and the patterns she's found that that quietly kill deals.This session is a practical look for founders and revenue leaders who want more out of AI outbound than volume.Follow Elaine: https://www.linkedin.com/in/elainezelby/Follow James: https://www.linkedin.com/in/jameskaikis/Read more from GTMshift: https://gtmshift.substack.com/---The AI-Fluent Revenue Leader was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_aifluentrevGradient: https://bit.ly/GradientVentures-aifluentrevCaptivate Talent: https://bit.ly/CaptivateTalent-aifluentrevClarify: https://bit.ly/Clarify-aifluentrevClay: https://bit.ly/Clay-aifluentrevOutworks: https://bit.ly/Outworks-aifluentrev

Kyle Duffy, Operating Partner at Gradient, has a conversation with James on how the profile of a great revenue leader is changing, what's now expected, and why getting hands-on wins.Follow Kyle: https://www.linkedin.com/in/kylerduffy/Follow James: https://www.linkedin.com/in/jameskaikis/Read more from GTMshift: https://gtmshift.substack.com/---The AI-Fluent Revenue Leader was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_aifluentrevGradient: https://bit.ly/GradientVentures-aifluentrevCaptivate Talent: https://bit.ly/CaptivateTalent-aifluentrevClarify: https://bit.ly/Clarify-aifluentrevClay: https://bit.ly/Clay-aifluentrevOutworks: https://bit.ly/Outworks-aifluentrev

Kyle Norton, CRO at Owner.com, sits down for an audience Q&A on building one of the most AI-forward sales orgs in B2B while scaling Owner from $2M to $100M. He fields questions on change management, rep enablement, and why most AI investments stall right after the demo.Follow Kyle: https://www.linkedin.com/in/kylecnorton/Follow James: https://www.linkedin.com/in/jameskaikis/Read more from GTMshift: https://gtmshift.substack.com/---The AI-Fluent Revenue Leader was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_aifluentrevGradient: https://bit.ly/GradientVentures-aifluentrevCaptivate Talent: https://bit.ly/CaptivateTalent-aifluentrevClarify: https://bit.ly/Clarify-aifluentrevClay: https://bit.ly/Clay-aifluentrevOutworks: https://bit.ly/Outworks-aifluentrev

Cristina Cordova has been an early operator at three of the most beloved software companies ever built. Stripe. Notion. Linear. Each one built a cult following before it built a sales team. That is not a coincidence.Now COO at Linear, Cristina joined the group at Engineering Tailwinds, a live event in San Francisco co-hosted by GTMshift and The Transaction, to share what she has learned about building GTM the hard way: without a famous brand, without a big sales org, and without shortcuts.Discussed in this episode:Why selling a transformation beats selling a better version of an existing toolHow Linear evolved its positioning from "the issue tracker you'll love" to a board-level AI conversationThe first principles mindset that Patrick Collison brought to Stripe and why Cristina has carried it everywhere sinceWhy the best salespeople at your company probably did not come from the category leaderLinear's work trial hiring process and why it reduces turnover on the sales teamHow to build a community moat and turn customers into your distribution channelWhy Linear went years without SDRs and what finally made outbound workHow to stay focused when investors, boards, and your own team are all pulling in different directionsWhat it means to do the dirty work in 2025 versus 2021 and why the answer has not changed as much as people thinkKey Takeaways:1. Sell the transformation, not the tool. "Better than Jira" gets you in the door with early adopters. It does not get you to a board-level conversation. The companies that break out are the ones that connect their product to a shift that is already happening in the market.2. Start narrow, then go wide. Stripe was payments for developers. Linear was the issue tracker you'd actually love. Both eventually had much bigger stories to tell. But they earned the right to tell them by winning a niche first.3. Hire salespeople who have had to fight for deals. Category leaders attract order-takers. The person at the number two or three company who had to build relationships, navigate procurement, and beat a dominant competitor is the one who will actually help you win.4. The work trial is worth it. Three paid days, a product demo, a sales pitch, and an account plan. Linear has less sales turnover because of this process. If someone cannot demo the product with confidence after three days, that tells you something important.5. First principles beat best practices. Just because every company has a sales ops hire at a certain stage does not mean you need one too. Ask why before you copy what worked somewhere else.6. Saying no is a system, not a habit. The most focused companies are explicit about what they are not doing. That list is as important as the roadmap.7. Build in public before you need to. Linear attracted talent, customers, and investors because the founders shared how they were building the company, not just what they were building. That only works if you start before you have something to lose.Follow Cristina: https://www.linkedin.com/in/cristinajcordova/Follow James: https://www.linkedin.com/in/jameskaikis/Follow Craig: https://www.linkedin.com/in/craigrosenberg/Follow Matt: https://www.linkedin.com/in/matt-amundson-91657236/Read more from GTMshift: https://gtmshift.substack.com/Produced in partnership with The Transactionhttps://thetransactionpod.comEngineering Tailwinds was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_GTMUserGems: https://bit.ly/UserGems_GTMAvarra: https://bit.ly/Avarra_GTMCaptivate Talent: https://bit.ly/CaptivateTalentStorypath: https://bit.ly/Storypath_GTM& LinkedIn

Carilu Dietrich took Atlassian public and has spent the years since advising some of the fastest-growing companies in B2B tech, including Lovable. Maya Spivak is the brand marketer behind campaigns for Segment, Lovable, LinkedIn, and Hightouch.Together, they have a simple thesis: most of what passes for B2B marketing right now is either derivative, tasteless, or both. The companies breaking through are doing something different.At Engineering Tailwinds, a live event in San Francisco co-hosted by GTMshift and The Transaction, Carilu and Maya joined the group to break down what is actually working, what is not, and why copying the thing that worked for someone else almost never works for you.Discussed in this episode:Why great products with word of mouth still beat everything else, including AI-powered distributionEdutainment as the foundation of modern B2B marketing and what it actually looks like in practiceThe PostHog campaign breakdown: what made it work in 2024 and why copying the format in 2026 is already a mistakeWhy Lovable's two most viral tweets of their first year were completely unplannedThe founder social playbook: how consistency builds pipeline and what separates it from vanity metricsWhy enterprise buyers are not visiting your website and where they are actually learning about youHow influencer strategy works in B2B, including micro influencers, and why it matters even for small budgetsThe "zig when others zag" principle: how to find your version of it instead of copying someone else'sWhat out-of-home advertising actually costs, who it works for, and what bad taste looks like in the wildWhy speed is the new creative constraint and what a 32-hour campaign launch actually requiresKey Takeaways:1. Nothing has changed about what makes marketing work. Great products that serve real needs, that people love and talk about. That is still the foundation. AI does not change that.2. Edutainment is not a tactic, it is the baseline. If your content is not entertaining, people scroll past it. The companies winning at RSA, on LinkedIn, and on billboards all understand this. The ones losing do not.3. Copying campaigns is the fastest way to look like you have no ideas. PostHog's injury attorney format worked because nobody had done it. The company biting the format on a bus in San Francisco right now is invisible.4. Viral is overrated. Consistency is underrated. Almost every marketer who has gone viral will tell you the same thing: it did not move the needle as much as they expected. What builds pipeline is showing up every week for a long time.5. Enterprise buyers are on LinkedIn, not your website. Fortune 100 buyers responsible for AI purchasing decisions are following industry leaders on LinkedIn and booking demos without ever visiting a website. Your founder's presence is your top-of-funnel.6. Zig when others zag, but find your own zig. The fuzzy heart works for Lovable. The wrestling ring works for Commvault at RSA. Neither of those works for you unless it is authentically yours and genuinely unexpected in your context.7. Taste is a competitive advantage. When you are spending real money on out-of-home, events, or social, the difference between good and mid is visible to everyone. Find the people in your orbit who have taste and listen to them.Follow Carilu: https://linkedin.com/in/cariludietrich/Follow Maya: https://www.linkedin.com/in/mayagrinbergspivak/Follow James: https://www.linkedin.com/in/jameskaikis/Follow Craig: https://www.linkedin.com/in/craigrosenberg/Follow Matt: https://www.linkedin.com/in/matt-amundson-91657236/Read more from GTMshift: https://gtmshift.substack.com/Produced in partnership with The Transactionhttps://thetransactionpod.comEngineering Tailwinds was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_GTMUserGems: https://bit.ly/UserGems_GTMAvarra: https://bit.ly/Avarra_GTMCaptivate Talent: https://bit.ly/CaptivateTalentStorypath: https://bit.ly/Storypath_GTM& LinkedIn

Most startups are invisible. Not because their product is bad, but because they're competing for attention the wrong way — with the same positioning, the same tactics, and the same noise as everyone else.Scott Albro has spent decades building startups and now works closely with a handful of early-stage founders every year helping them solve one problem above all others: the attention crisis.At Engineering Tailwinds, a live event in San Francisco co-hosted by GTMshift and The Transaction, Scott joined the group to break down why the old GTM playbook is failing and what actually works when your default setting as a startup is obscurity.Discussed in this episode:Why everything in today's market is downstream of attention and what that means for early-stage GTMThe difference between viewing your market as a target account list versus a network and why it changes everythingWhat 10x hubs are, how to identify them, and how Clay and Granola used them to break throughWhy most founder brand content is doing more harm than good and what to do insteadThe three story types every startup needs to be able to tell: customer story, personal journey, and transformation storyWhat makes a narrative dominant versus forgettableHow to flip the push-to-pull ratio and what it actually looks like when you get it rightWhy ServiceTitan's narrative is the best GTM story of the last 20 years and what you can steal from itKey Takeaways:1. Obscurity is the default. Attention is the job. Nobody is waiting for your startup. The market doesn't care. Getting attention is not a marketing problem, it's a strategic one that starts with how you think about your market.2. Your market is a network, not a list. Target accounts give you funnel leverage. Thinking in networks gives you strategic leverage. Find the 10x hubs that connect to your buyers and infect them with your narrative.3. The transformation story is the most powerful story type right now. Status quo, future vision, and a prescriptive journey from here to there. The best narratives make the customer the hero and position the company as the guide.4. Founder brand done wrong is a liability. Getting 100 likes on a cringe post doesn't build brand, it erodes it. The goal is to become personally synonymous with the category you're building, not to rack up impressions.5. Distribution is an experiment, not a plan. The best companies treat distribution tactics as continuous rapid experimentation. Double down on what works, jettison what doesn't. That requires a system.6. Authenticity is earned, not performed. You don't need to have grown up in the trades to tell ServiceTitan's story. But you do need to immerse yourself in your customer's life until you genuinely understand it. That's what makes a narrative believable.Follow Scott: https://www.linkedin.com/in/scottalbro/Follow James: https://www.linkedin.com/in/jameskaikis/Follow Craig: https://www.linkedin.com/in/craigrosenberg/Follow Matt: https://www.linkedin.com/in/matt-amundson-91657236/Read more from GTMshift: https://gtmshift.substack.com/Produced in partnership with The Transactionhttps://thetransactionpod.comEngineering Tailwinds was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_GTMUserGems: https://bit.ly/UserGems_GTMAvarra: https://bit.ly/Avarra_GTMCaptivate Talent: https://bit.ly/CaptivateTalentStorypath: https://bit.ly/Storypath_GTM& LinkedIn

51% of B2B buyers now start their research in an LLM, not Google. A year ago that number was 24%. That shift happened in 12 months, and most GTM teams aren't ready for it.Sydney Sloan has been studying this longer than almost anyone. As CMO at G2, she sits on top of one of the most cited data sources in the entire AI research ecosystem, and she's watched buyer behavior change in real time.At Engineering Tailwinds, a live event in San Francisco co-hosted by GTMshift and The Transaction, Sydney joined the group to break down exactly what Answer Engine Optimization is, why it matters more than most teams realize, and what to actually do about it today.Discussed in this episode:Why 51% of buyers now start their research in an LLM and what that means for your pipelineAEO vs. GEO: what the terms actually mean and why the distinction mattersHow G2 architected their content to become one of the top citation sources for AI research toolsWhy the shortlists AI returns are shrinking and how to make sure you're on themThe two tactics nobody is talking about yet: G2 discussions and community forums as LLM citation sourcesWhy PR is back and how to use it for AEO, not just brand awarenessHow to think about content freshness, page pruning, and the math of LLM indexingThe consensus signal amplification strategy: how to get the same answer surfaced in multiple places so the LLM treats it as truthSelf-reported attribution: why it's making a comeback and how to automate itKey Takeaways:1. Where your buyers do research has changed faster than anyone expected. 51% of B2B buyers start in an LLM today. That number doubled in a year. Your brand needs to show up where they're looking, not where they used to look.2. Own the answer, not just the keyword. AEO is about being the definitive response to the questions your buyers are actually asking. Think in question-and-answer format, not in blog posts.3. Citation sources are the new backlinks. G2, Reddit, and partner pages are where LLMs go to validate answers. If you're not investing in those placements, you're invisible to a growing share of your market.4. Consensus signal amplification is the game. When an LLM sees the same answer in multiple places, it treats that as authoritative. Replicate your core answers across your site, partners, G2, communities, and influencer content.5. Content freshness beats content age. LLMs favor recency. Take your top SEO pages and build AEO versions. Prune the rest. G2 cut their site by 25-30% and saw results.6. PR is back, but for different reasons. Publications that have structured partnerships with AI vendors are being cited heavily. A VentureBeat placement or Forbes Contributor post is now an LLM visibility play, not just a brand play.7. Start with the AEO tool. You can't track what you can't see. Before you build a content strategy, buy a tool that shows you what questions are being asked, what's being cited, and where you're showing up versus competitors.Follow Sydney: https://www.linkedin.com/in/sydsloan/Follow James: https://www.linkedin.com/in/jameskaikis/Follow Craig: https://www.linkedin.com/in/craigrosenberg/Follow Matt: https://www.linkedin.com/in/matt-amundson-91657236/Read more from GTMshift: https://gtmshift.substack.com/Produced in partnership with The Transactionhttps://thetransactionpod.comEngineering Tailwinds was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_GTMUserGems: https://bit.ly/UserGems_GTMAvarra: https://bit.ly/Avarra_GTMCaptivate Talent: https://bit.ly/CaptivateTalentStorypath: https://bit.ly/Storypath_GTM& LinkedIn

Chris Degnan was the first sales rep at Snowflake. He took a 50% pay cut, joined a room full of engineers, and was told he probably wouldn't close a deal for two years. Eleven years later, he was CRO of one of the largest software IPOs in history.This isn't a highlight reel. It's the actual playbook: what it takes to find product-market fit, build a GTM engine, and sell when conditions aren't perfect.At Engineering Tailwinds, a live event in San Francisco co-hosted by GTMshift and The Transaction, Chris joined the group to dig into what separates the operators who survive the grind from those who don't.Discussed in this episode:Why desperation is the most underrated quality in early sales hiresHow Chris found product-market fit in AdTech and Online Gaming after the product broke under loadThe "this week, last week" transparency email that turned sales intel into product roadmapThe Top 100 account framework that fixed Snowflake's demand generation problem overnightWhy Chris eliminated standalone customer success and what replaced itThe feedback loop with John McMahon that kept a CRO in seat for 11 years when the average tenure is 18 monthsWhy qualified meetings beat MQLs every timeWhat it actually looks like to build pipeline from zero when nobody's heard of youKey Takeaways:1. Hire for desperation, not pedigree. Big-company reps inherit playbooks. Early-stage reps have to build them. Know which one you need and don't confuse the two.2. Be the student of what you sell. Chris knew Snowflake's product, pricing, and contracts better than almost anyone in the company. That's how he earned credibility with engineers and customers alike.3. Drop MQLs. Measure qualified meetings. When Denise Persson came in as CMO, she stopped talking about MQLs entirely. The only thing that counted was whether the sales team was in front of the right customers.4. Transparency compounds. A weekly "this week, last week" email sent to the entire company, board included, created alignment, accountability, and product feedback loops that shaped Snowflake's roadmap.5. When there's doubt, there's no doubt. Frank Slootman's rule. If someone's wrong for the role, fixing it fast is an act of leadership, not cruelty.6. Customer success is everyone's job. Chris scrapped standalone CS and embedded accountability into sales and SEs. Customers who paid for professional services were more successful. Incentives matter.Grab Chris's book: Make It Snow — makeitsnowbook.comFollow Chris: https://www.linkedin.com/in/chris-degnan/Follow James: https://www.linkedin.com/in/jameskaikis/Follow Craig: https://www.linkedin.com/in/craigrosenberg/Follow Matt: https://www.linkedin.com/in/matt-amundson-91657236/Read more from GTMshift: https://gtmshift.substack.com/Produced in partnership with The Transactionhttps://thetransactionpod.comEngineering Tailwinds was made possible by our sponsors:FullEnrich: https://bit.ly/FullEnrich_GTMUserGems: https://bit.ly/UserGems_GTMAvarra: https://bit.ly/Avarra_GTMCaptivate Talent: https://bit.ly/CaptivateTalentStorypath: https://bit.ly/Storypath_GTM& LinkedIn

James Kaikis interviews Kyle Norton, CRO at Owner.com, about driving transformative SaaS growth. Kyle shares how Owner.com achieved 10x revenue growth in two years through strategies like centralized lead research and customer-focused comp plans. They discuss the evolving CRO role, the importance of enablement and rev ops, and actionable AI applications. Learn how to scale smartly, foster customer-centric growth, and build high-performing teams. Tune in for tactical insights to create your SaaS success playbook.Jump into the conversation:(00:00) Welcome to the Episode(04:30) Kyle’s Journey (09:15) Scaling Through Customer-Centricity(15:45) Investing in Enablement and RevOps(21:30) Hiring for Growth Mindset and Curiosity(28:40) Transitioning Trust Post-Sale(34:50) Leveraging AI for Internal Efficiency(42:15) The Future of Sales Roles in SaaS(50:00) Unconventional GTM Strategies for the FutureThis episode is sponsored by TestBox. Please visit www.testbox.com to learn more! This episode originally premiered on The New GTM Playbook. Watch the original: www.testbox.com/gtmWatch This Episode on YouTube: https://youtu.be/BNr6iIqWDZ8Follow Kyle on LinkedIn: https://www.linkedin.com/in/kylecnorton/More from The GTMshift: www.gtmshift.comSubscribe to the newsletter: https://gtmshift.substack.com/Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/