GTM News Desk: Why Onboarding at an AI-Native Company Broke Her Definition of Fast

After six months and a run of conversations spanning Reddit, YouTube, website conversion, and onboarding, Mark Kilens and Natalie Marcotullio are hitting pause on GTM News Desk, at least in this format. In our final episode together, we look back at what actually stuck from a season of go-to-market experiments, why "there's no playbook" is the most honest advice they can give anyone joining a startup, and why over-polishing a campaign or a doc is a losing bet in 2026.We also make their predictions for the next six to twelve months: Natalie argues AI agents becoming the primary buyer is overhyped for now, and Mark thinks the industry is closer to a bubble-bursting moment than most people are willing to admit. Plus, a look at what's to come: Natalie is bringing back her Revenue on the Rocks podcast and Mark is launching a new newsletter on people-first go-to-market.Jump into the action: (00:00) Reflecting on where the AI slop cycle stands now (00:25) Catching up before the show (02:16) Six months, and a look back at every episode (03:57) The go-to-market map they've covered, guest by guest (07:01) Why there's no playbook when you join a startup (08:55) Prioritizing through experimentation instead of debate (11:18) Natalie teases the return of Revenue on the Rocks (12:42) Mark teases a new people-first go-to-market newsletter (14:47) Prediction: why AI agents won't be buying software yet (15:39) Prediction: the AI bubble-bursting moment (18:23) Critical thinking atrophy and AI fatigue (20:07) Mark's teaser for a Navattic product launch postSubscribe to Mark’s Newsletter, People-First GTM: https://people-first-gtm.beehiiv.com/Listen to Natalie’s Podcast, Revenue on the Rocks: https://www.navattic.com/revenue-on-the-rocks

As we discussed in our last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day.Pragmatico Head of Marketing Lindsay O'Brien shares her experiences on what changed for her two months into a fully AI-native company after spending the last year as one of the earliest marketers building Claude skills for brand guidelines. The conversation gets into what actually gets evaluated in an AI-native interview process, why mandating AI adoption through shame backfires, and the Claude skill Lindsay built that plans an entire marketing event end to end. Lindsay also makes the case for why a unique point of view has to come before any AI workflow, and why skipping that step is the real reason so much AI-assisted content reads as forgettable.Jump into the action: (00:00) Why project management eats as much time as the work itself (00:32) Catching up before the show (11:45) A full circle moment for Mark, Natalie, and Lindsay (14:03) How to approach AI change management step by step (16:46) The Claude Cowork token trap (20:12) The critical thinking piece: don't outsource your point of view (23:02) The four-step cycle for company-wide AI transformation (27:24) The Claude skill that plans an entire marketing event (33:33) How to pull context straight from the codebase (36:06) Who owns the deck when anyone can make one (43:20) Turning marketing into an assembly line (45:26) Why a unique point of view matters more than more context (48:07) Will AI ever feel as boring and as useful as ExcelConnect with Lindsay O'Brien: https://www.linkedin.com/in/lindsaykenders/

As we discussed in our last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day.Ross Simmonds, founder of Foundation and the person who was telling B2B brands to get on Reddit back in 2016, joins Mark and Natalie to discuss what that admission actually means for marketers. Ross walks through why he bet on Reddit and Quora years before anyone else cared, how a fantasy football blog in college turned into a content marketing company, and why he thinks YouTube is the next channel everyone is sleeping on.The conversation also covers the difference between commodity and non-commodity content, why volume plays on programmatic SEO are a fast track to getting deindexed, and how to reverse-engineer what a community actually wants before you post to it.Jump into action:(00:00) Why AI is a blessing and a curse for marketers(00:41) Catching up while moving(03:43) Seth Godin asked Google's AI what happened to blogs(11:47) Ross on calling the Reddit wave back in 2016(17:52) The three times Google admitted to killing the open web(19:55) Why 10 blue links are never coming back(24:53) Commodity content versus non-commodity content(28:48) Turning one report into dozens of micro assets(29:47) The brand, product, and content marketing trifecta(39:46) Why leadership teams are pressuring the wrong metrics(44:24) Why AI visibility tools are still just directional(49:29) The next underinvested channel is YouTube(52:13) Ross's take on webinarsConnect with Ross Simmonds: https://www.linkedin.com/in/rosssimmonds/Check out Foundation: https://foundationinc.co/Read Blogs, Traffic, and Google by Seth’s Blog: https://seths.blog/2026/06/blogs-traffic-and-google/ Produced in partnership with Share Your Genius: https://shareyourgenius.com/

As we discussed in our last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day.Bryn Jones, co-founder of Partnerstack, breaks down how partnerships evolved from channel deals into full ecosystem orchestration, and why the companies winning at it treat every partner like part of the team. He shares the two questions that decide which partner types fit your business, why alignment with your executive team matters more than headcount, and the exact way to go from zero partners to a program that scales.Bryn also gets into the 80/20 rule of activated partners, why software attribution is getting harder instead of easier, and the rookie mistake that ends new partner managers' careers by day 50.Jump into the action:(00:00) Bryn on why partners who feel like part of your team will drive revenue for you(00:29) Mark and Natalie catch up from Maine and New York City(04:00) The mom-and-pop SaaS debate and what it means for mid-market software(10:30) Meet Bryn Jones, co-founder of PartnerStack(14:25) Why "partner program" and "partner ecosystem" aren't the same thing(21:20) The two factors that decide which partner types fit your business(25:16) How many partners you actually need to start (it's not 50)(29:34) Why software-based attribution is getting harder, not easier(35:03) Why refer-a-friend programs are a source of learning, not revenue(38:53) Using customers as a source of partner references(40:12) Tactical tips for starting outbound partner recruitment(41:49) The rookie mistake that gets new partner managers fired by day 50Connect with Bryn Jones: https://www.linkedin.com/in/bryn-jones/Check out PartnerStack: https://partnerstack.com/Read The Mom-and-Pop SaaS era has arrived by Elena Verna: https://www.elenaverna.com/p/the-mom-and-pop-saas-era-has-arrivedProduced in partnership with Share Your Genius: https://shareyourgenius.com/

As we discussed in our last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day. In this episode, Ramli John, founder of DelightPath and author of Eureka, pushes back on the ship-it-and-see mindset sweeping through B2B. He explains why reducing time-to-value too aggressively can wreck week-one retention, how friction is actually necessary for learning, and why the teams winning with AI right now are the ones going deep on one thing, not wide on twenty.Ramli also shares a first look at his upcoming book, Delightful Intelligence, and why the principles behind great onboarding haven't changed just because there's a chat box on the screen.Jump into the action:(00:00) Why AI acts like an eager intern who agrees with everything(02:37) Pew Research: More US adults concerned about AI than excited (04:16) AI fatigue is real—news cycles, layoffs, and broken efficiency promises(08:27) The shortcut mindset AI is creating inside teams(12:24) What the best AI models look like (17:10) Meet Ramli John, founder of DelightPath(19:59) Why great onboarding in the AI era still starts with core principles(25:32) The EUREKA framework: a cross-functional approach to onboarding(30:12) Why friction is not the enemy in user onboarding(35:00) Chat interfaces vs. MCPs: What actually reduces onboarding friction(40:44) The blank page problem and why "it can do anything" is terrible UX(43:32) How many product updates can your users actually absorb?(45:49) The right way to roll out a navigation change(49:45) Why human conversations matter more than ever in a vibe-coded world(52:16) Why Claude is beating OpenAI by playing the long gameConnect with Ramli John: https://www.linkedin.com/in/ramlijohn/Check out DelightPath: https://delightpath.com/Get Eureka: The Product Onboarding Playbook for High-Growth B2B Companies: https://www.damngravity.com/products/eureka-by-ramli-john Produced in partnership with Share Your Genius: https://shareyourgenius.com/Resources:Key findings about how Americans view AI: https://www.pewresearch.org/short-reads/2026/03/12/key-findings-about-how-americans-view-artificial-intelligence/The 2026 AI Index Report: https://hai.stanford.edu/ai-index/2026-ai-index-report

As we discussed in our last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day. In this episode, Roee Hartuv, founder of Willingness to Pay, uncovers the truth about pricing and packaging in today’s rapidly evolving tech landscape. Roee explains why the old “good, better, best” model may no longer cut it and how the Jobs-to-Be-Done framework offers a more customer-centric approach. He goes into how businesses can transition to more dynamic pricing models, including credit and usage-based strategies, to meet the growing demands of AI-powered solutions.He discusses real-world examples from his work with SaaS and AI-driven companies, offering practical insights on how to keep margins healthy without sacrificing value or transparency. Roee gives us a look at how AI integration is reshaping the pricing landscape and why businesses need to rethink traditional models to avoid margin erosion.Jump into the action:(00:00) Why pricing models are more than just numbers(03:09) AI products need a new pricing strategy(14:37) What Jobs to Be Done reveals about pricing and value(15:22) The "good, better, best" model isn't enough anymore(22:39) Should AI-driven businesses always adopt value-based pricing?(23:33) How AI pricing examples are shaping future business models(24:58) How AI is challenging traditional pricing models(34:46) Pricing for enterprise and smaller customers without sacrificing simplicity(37:27) The importance of transparency in pricing(39:38) Why customer journeys are key to the right pricing structure(43:46) Roee's tips on testing and refining your pricing modelsConnect with Roee Hartuv: https://www.linkedin.com/in/roeehartuv/ Check out: https://www.willingnesstopay.com/ Produced in partnership with Share Your Genius: https://shareyourgenius.com/

As we discussed in our last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day. In this episode, Mojo Founder Eric Holland and Messaging Whisperer Anna Furmanov reveal what's really broken about how B2B companies develop and distribute their messaging. They dig into why most customer research is pulled from the most biased data available and how to document your decision-making, not just your knowledge, so AI can actually replicate your judgment. They also provide answers to why chasing every new AI workflow is making most marketers worse, not faster. Eric and Anna challenge the idea that volume of insights equals quality of insights, arguing that a single finding that changes how your whole company goes to market is worth more than a hundred tagged Gong quotes.Jump into the action:(00:00) Why B2B research should make you emotional about a lip balm(00:35) What CMOs are actually talking about at conferences right now(04:40) How shame and fear became the default AI adoption strategy(08:41) The difference between AI-exhausted and AI-excited teams(12:44) Four Tendencies and what it means for AI adoption(16:31) Why B2B messaging is broken even at well-funded startups(19:14) What separates Mojo from just pointing Claude at your Notion(27:26) What good writing actually feels like and whether AI can get there(32:17) The solar plexus test and how to know when your copy is working(34:05) Why nuance and emotion are the real gap in AI writing(39:27) Why most insight tools are just pattern-matching machines(44:19) How to check if your researcher is actually any good(47:30) The danger of everyone using the same tools to find the same answers(50:01) What B2B marketing gets wrong that B2C figured out long ago(53:21) Go deep on one thing for a quarter(55:22) Why you should only build what you already know coldConnect with Eric Holland: https://www.linkedin.com/in/eric-holland-not-a-marketer/ Connect with Anna Furmanov: https://www.linkedin.com/in/annafurmanov/ Check out: https://mojopmm.com/ Produced in partnership with Share Your Genius: https://shareyourgenius.com/

As we discussed in our last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day. In this episode, Camille Trent, Content Marketing Lead at Auror, breaks down what it takes to build stronger B2B content in an AI-shaped world. She shares how marketers can turn transcripts, customer conversations, and internal knowledge into better campaigns, why long-form content still works when it’s sharp and well edited, and how content, product marketing, and SEO are becoming more connected than ever. Camille also digs into the balance between creativity and brand fit, arguing that great content starts with knowing your audience and creating something worth their time.

As we discussed in our last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day. In this episode, Keith Frankel, CEO of Totango, shares his bold approach to customer success and growth. He explains why traditional metrics fall short and reveals how businesses can shift from product-driven to customer-led growth. Keith delves into the concept of value-driven alignment and discusses how AI is shaping the future of customer success. The conversation also tackles a broader shift in SaaS: if AI makes product features easy to replicate, companies will need new ways to stand out. Keith believes the answer isn’t product; it’s culture and operating DNA.

As we discussed in the last episode, we are taking a pause from Revenue on the Rocks while Ben is on paternity leave. During this time, we'll be sharing episodes from another podcast I am co-hosting: GTM News Desk with Mark Kilens. GTM News Desk also talks about buyer-first best practices and interviews marketers who are experts in them in their day-to-day. In this episode, Product Growth Expert Anastasia Kudrow shares her insights on understanding user behavior and applying psychological principles to enhance product-led growth. Anastasia reveals how to turn complex challenges into growth opportunities, offering strategies that help teams drive conversions and scale effectively.