The GTM Podcast

• GTM 143: Why Most AI Messaging Fails and How to Actually Stand Out in a Crowded Market | Harmony Anderson

  Harmony Anderson is an entrepreneurial marketing leader with deep expertise in building global GTM strategies at growth startups. She is currently the VP of Growth and Marketing at Superhuman, the most productive email app ever made for teams. She has also led high-performing teams at Armada, Engine, Outreach, and ThousandEyes.She is deeply passionate about creating world-class marketing campaigns, leveraging data-driven strategies to accelerate customer acquisition, engagement, and retention. She also drives extreme rigor around operational excellence and efficiency, ensuring GTM teams execute with precision using repeatable and predictable playbooks. Discussed in this Episode:How to develop unique positioning and messaging for an AI companyWhy UGC matters for your brand and how to get users to create content about your productThe impact of lightning marketing campaigns and follow-on 'thunder' campaignsThree core channels for launching a new B2B marketing programHighlights: 05:12 – The #1 mistake in AI messaging: sounding like everyone else. 07:24 – Use outcomes and data to differentiate your AI product. 11:06 – Why nailing 3-5 core use cases beats going broad or too niche. 12:38 – Turning website visitors into believers with demos and interactive content. 14:01 – How to keep up with a market that changes every week (hello, agentic AI). 15:08 – Building campaigns that fuel your narrative across every channel. 17:16 – Behind Superhuman’s most successful campaign ever: “New Year, New Inbox.” 20:04 – Unlocking 60% growth through user-generated content and affiliate advocacy. 21:38 – Why webinars and virtual events still drive real results (and feedback). 23:12 – How to keep your messaging fresh while staying focused. 25:11 – The difference between brand umbrella, campaign, and program — and why it matters. 27:02 – Harmony’s lean, high-impact program playbook for early-stage teams. 31:06 – Building a hype train: how to activate champions at launch. 33:01 – Hot take: marketing shouldn’t be measured by pipeline alone. 35:12 – Why NRR (not just pipeline) should be a marketing KPI.Guest Speaker Links (Harmony Anderson):LinkedIn: linkedin.com/in/harmony-hickman-andersonSuperhuman: superhuman.comHost Speaker Links (Sophie Buonassisi):LinkedIn: linkedin.com/in/sophiebuonassisiNewsletter: gtmnow.com/tag/newsletterWhere to find GTMnow (GTMfund’s media brand):Website: gtmnow.comLinkedIn: GTMnowX/Twitter: @GTMnow_YouTube: The GTM Podcast The GTM 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 142: Why Most B2B Marketing Fails (And How to Fix It) with Udi Ledergor

  Udi Ledergor served as CMO during Gong’s rise from new SaaS startup to industry dominance. By building a playful, human-centric brand with a lighthearted tone, he captured buyers’ attention and dollars and turned them into raving fans. He helped Gong go from zero to hundreds of millions in revenue, while achieving a multi-billion-dollar valuation. His book Courageous Marketing is officially out and you can buy it below in the show notes. Discussed in this Episode:Why Marketing 'Best Practices' are broken for Brands that want to stand out.Marketers need to consider the long game and remember the 95/5 rule.When you should hire for experience versus potential.How to foster a culture of healthy risk-taking with your team.Highlights: 04:09 Udi's inspiration for writing his new book, Courageous Marketing.06:02 The four most common reasons why marketing fails.09:22 What marketers should be looking for when selecting a company to join.13:55 The Problem with 'playing it safe' in B2B marketing.23:07 How to market to both the 5% and the 95% of your buyers.38:13 The Three Team Operating Principles for leading a bold and effective marketing team.Guest Speaker Links (Udi Ledergor):LinkedIn: https://www.linkedin.com/in/udiledergor/Gong: https://www.gong.io/Udi's Book, Courageous Marketing: https://mybook.to/courageousmarketingHost Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://gtmnow.com/tag/newsletter/Where to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube:    / @gtm_now  The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/Sponsor: ZoomInfo’s GTM25 Virtual Conference—a free, half-day event on hThe GTM Podcast The GTM 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 141: Timeless Growth Tips From a $7.4B Oracle Exit and Scaling Carta to $450M in Revenue | Jeff Perry

  Jeff Perry is a truly iconic revenue leader and the Chief Revenue Officer (CRO) at Carta, responsible for core software revenue across New Business, Upsell, Cross Sell, and Customer Success. Prior to Carta, Jeff led SMB Sales at DocuSign, and started his career at Oracle, where he rose from Strategic Account Manager to VP of Sales over a decade.Discussed in this Episode:How to turn coworkers into mentors—and why it matters.Moving from enterprise sales leadership to a startup environment.Why and when to build a solutions engineering team.The myth of the “18-month CRO lifespan.”Balancing empathy and accountability as a sales leader.Why automation isn’t always the best path forward.Highlights: 06:29 — Mentorship matters. Jeff breaks down how to find and approach mentors—even without a formal program.12:42 — Lessons from selling servers that still apply to modern SaaS sales15:02 — Leading through M&A: Inside the culture clash and how Jeff rebuilt a team post-acquisition.19:07 — Carta’s GTM evolution: How Jeff scaled from one rep selling one product to multiple teams across three business lines.28:34 — Scaling revenue from $20M to $450M: Advice for CROs entering growth-stage companies.33:20 — Why “big company” people can thrive in startups—if they leave their playbooks behind.36:15 — How to use PIPs to coach—not just cut—and what most orgs get wrong.43:13 — Why the best sellers are quarterbacks, not lone wolves.46:43 — Pick up the phone: Human connection wins in an era of AI and automation.Guest Links (Jeff Perry): LinkedIn: Jeff Perry Carta: carta.comHost Links (Scott Barker): LinkedIn: Scott Barker Newsletter: The GTM NewsletterWhere to Find GTMnow (GTMfund’s Media Brand): Website: gtmnow.com LinkedIn: GTMnow Twitter/X: @GTMnow_ YouTube: @gtm_now Podcast: The GTM Podcast (available on all major platforms)Sponsor: PursuitThe best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.If you're hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.The GTM Podcast The GTM 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 140: How Microsoft Scaled from $600M to $5B: The Enterprise Playbook with Hayden Stafford

  Hayden Stafford is the President and Chief Revenue Officer (CRO) at Seismic, where he oversees the global go-to-market (GTM) organization, including pre-sales, sales, customer success, services, partners, and more. Prior to joining Seismic, he served as President of Global Field Operations at Pegasystems. Before that, Hayden was Corporate Vice President at Microsoft, leading Global Business Applications (Microsoft Dynamics 365) for six years. Earlier in his career, he was an SVP at Salesforce and spent nearly a decade at IBM, ultimately serving as VP and Managing Director on Wall Street.Discussed in this Episode:What Satya Nadella taught Hayden about culture, clarity, and transformation at Microsoft.The exact playbook to move from SMB to enterprise—including partner enablement, segmentation, and incentive design.Why retention isn't just a CS metric—and how to build a sales team that cares about it.How to win in vertical SaaS, from breaking into financial services to owning the category.What it takes to close a $600M+ deal in the middle of a financial crisis.Highlights: 05:19 — How Satya Nadella sold his internal vision and rebuilt Microsoft’s culture from the ground up 13:13 — The partnership blueprint: how to scale with partners, not just transact with them 28:18 — Going deep in verticals: why Seismic dominated financial services while others avoided it 34:44 — How Hayden closed a $600M+ deal with Merrill Lynch after the 2008 crash 42:40 — Why retention should be part of your sales comp—and how to make it work 49:15 — The “Value Continuum”: a framework for aligning sales, services, and CS around business outcomesGuest Speaker Links (Hayden Stafford):LinkedIn: https://www.linkedin.com/in/haydenestafford/Seismic: https://seismic.com/Host Speaker Links (Scott Barker):LinkedIn: https://www.linkedin.com/in/ssbarker/Newsletter: https://thegtmnewsletter.substack.com/Where to find GTMnow (GTMfund’s media brand):WebsiteLinkedInTwitter / XYouTubeThe GTM Podcast (on all major directories)The GTM Podcast The GTM 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 139: AI Agents Are Changing Everything — Microsoft’s VP of AI Agents on the New Era of Work and Software | Ray Smith

  Ray Smith is the VP of AI Agents at Microsoft. Previously, he was the Global VP of Product for SAP, CRM and Sales Cloud. Before that, he was the CEO and Co-Founder of DataHug, which was acquired by Calidus Cloud in 2016. Ray breaks down why the rise of AI agents is a tectonic shift, how businesses are already seeing ROI, and what it means for SaaS, team structure, and go-to-market strategies. He also shares real-world use cases from inside Microsoft and partner companies, plus how founders and operators can build or adapt in this new AI-native era.Discussed in this Episode:What exactly is an AI agent—and how is it different from bots or automation?Why traditional SaaS pricing models (like per-seat) don’t work in the agent era.How enterprise teams are already deploying autonomous agents in production.The emerging architecture of multi-agent workflows.Which skills will matter most in an agent-first world (hint: think like a GM or growth hacker).Highlights: 06:53 What makes an AI agent different from bots and automation—and why it matters now.15:33 How AI agents are changing the role of traditional software tools and UI.25:15 Why legacy SaaS pricing models don’t work for agents—and what comes next.31:12 Inside Microsoft CoPilot: Real-world agent use cases across sales, support, and strategy.37:42 The most valuable skills in the AI era—from delegation to agent orchestration.51:42 Why agentic AI makes customer relationships and long-term value even more critical.Guest Speaker Links (Ray Smith):LinkedIn: https://www.linkedin.com/in/raycsmith/Host Speaker Links (Scott Barker):LinkedIn: https://www.linkedin.com/in/ssbarker/Newsletter: https://thegtmnewsletter.substack.com/Where to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube:    / @gtm_now  The GTM Podcast (on all major directories): The GTM Podcast The GTM 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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