The Thread Podcast

Justin Vandehey
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The Thread Podcast explores the future of enterprise sales in the era of AI.  Hosted by Justin Vandehey, founder of Thread, we bring together top sales leaders, enablement pros, and innovators shaping how go-to-market teams grow and win. Each episode dives deep into what’s changing in sales—from real-time AI coaching to modern revenue systems of action—and features actionable insights from CROs, RevOps leaders, startup founders, and the technologists building the next generation of tools. Whether you’re scaling founder-led sales or leading a global GTM team, you’ll walk away with new strategies to improve seller performance, accelerate deal cycles, and leverage AI for growth. If you’re ready to think differently about sales execution and the future of GTM, follow The Thread and join the conversation.

  1. 4D AGO

    Your Next Role Won't Be Posted, It'll Be Whispered — Andy Mowat

    Andy Mowat has run RevOps at four unicorns, and between every role he's gone out and built something new. His latest is Whispered, an AI platform that helps top GTM execs build their careers through shared insights, warm introductions, and access to the roles that never get posted. In this episode, Andy and Justin get into why the entire GTM tech stack is heading for a two-year rebuild, what the move to a data-warehouse-first model means for RevOps teams, and why smaller companies are suddenly more nimble than the enterprise. Andy shares hard-won lessons from scaling Culture Amp, including the speed-to-lead system he built around time-critical leads and the market-maturity question he buried in the win-loss forms. They also dig into whether the fractional exec wave is real, why thoughtful gifting and distinctive events still beat automated outbound, and what it actually feels like to run a proactive job search at the VP level for the first time. A candid conversation between two friends about category strategy, positioning, and building a career in go-to-market when the ground keeps shifting. Buzzsprout Chapter Markers 00:00 — Intro: how Justin and Andy met around Culture Amp  01:40 — Andy's background: RevOps at four unicorns, and why he keeps building  03:30 — Founders as a hiring profile, and the trap of "ambiguous roles"  05:30 — Rebuilding the GTM tech stack: data warehouse first, the semantic layer, and two years of turmoil  07:00 — The give-to-get ratio and why AI-era outbound still comes down to better emails  08:30 — Strategic gifting, distinctive events, and the Wisconsin business school cold open  11:00 — Podcasts as relationship engines, not just content  11:30 — Inside Culture Amp: 180 events a year and the speed-to-lead system  13:00 — The multi-prospect demo experiment, and the market-maturity question that predicts a category's breakout 14:45 — The fractional exec wave: real shift or euphemism for "between jobs" 16:15 — Why early-stage marketing needs people to "grok what you do" before top of funnel  18:00 — What's next for Whispered: the network, the community, and the roles that get whispered

    27 min

  2. MAY 8

    You Can't Read the Label from Inside the Bottle

    Justin sits down with Nils Vinje, business growth guide and longtime customer success leader, to talk about the single biggest thing holding most growing companies back: everything still depends on the CEO. Nils spent the early part of his career on the leading edge of the customer success movement — convincing his first employer to ditch the "account manager" title back in 2011 — and has since coached hundreds of CS and CX leaders through the challenge of making their function legible to the rest of the organization. These days he works with CEOs and their leadership teams using the Pinnacle system, a five-principle framework built around people, purpose, playbooks, performance, and profit. In this conversation, Nils and Justin get into what running a CX org teaches you about leadership that no other function can, how to read the label from outside the bottle, and why the hardest decisions in any company are usually the ones everyone already knows need to be made. He also shares what he'd ask anyone standing at a crossroads in their career — and why the answer has nothing to do with money. Chapters [00:00] Intro and What Nils Does Now  [01:42] What Leading a CX Org Teaches You About Leadership  [03:30] The Single Biggest Challenge Every CS Leader Faces  [05:01] Who Nils Works With and When to Bring in Outside Help  [07:08] The Pinnacle System — Five Principles for a Well-Oiled Machine  [09:38] Delivering Hard Truths with Grace  [11:00] The People Problem Most CEOs Won't Solve  [13:08] Why Being Inside the Bottle Kills Objectivity  [14:29] The First Question Nils Asks Anyone at a Career Crossroads  [16:25] What's Next for Nils and the Growth Bottleneck Blueprint  [18:34] Never Stop Adding Value

    24 min

  3. APR 24

    From Cisco to IBM: How Professional Services Became the Most Important Role in Enterprise Tech w/ Sanjay Pal, WW VP of Software Professional Services at IBM

    Justin sits down with Sanjay Pal, Worldwide VP of Professional Services at IBM, to explore what it really takes to lead services at global scale and why the role is more strategically important now than ever before. Sanjay draws on his journey from Cisco to Accenture to IBM to break down what has fundamentally changed about services delivery in the AI era, and what has stayed the same. He shares how IBM thinks about standardizing delivery across 16 global markets without sacrificing client experience, why the forward-deployed engineer model is gaining momentum, and how professional services leaders need to evolve from deployment executors into trusted business advisors. He also shares a personal story about his father, who wrote 52 books with pen, paper, and a stack of research clippings, and what that means for what's possible now. Chapters [00:00] Intro and Sanjay's Path to IBM [02:33] What's Changed in Services, and What Hasn't [05:00] How AI Amplifies Delivery Without Replacing Judgment [08:01] Standardization vs. Customization at Global Scale [10:38] The Evolving Role of the Services Leader [12:44] Forward-Deployed Engineers and Leading with Services [15:02] Breaking Down Silos Across Pre-Sales, Implementation, and Post-Sales [16:05] What's Top of Mind Heading into 2026

    21 min

  4. APR 10

    From 265 Million Users to Enterprise Gold Standard: How Canva Scales GTM Without Losing Its Soul

    Justin sits down with Jessica Chiew, Global Head of GTM Strategy and Operations at Canva, to unpack what it really takes to evolve from a beloved PLG product into a full-fledged enterprise sales machine without breaking what made it great. Jessica shares how Canva navigates the complexity of multiple handoffs across a PLG-to-SLG journey, why time to value is everyone's job (not just CS), and how she's thinking about marrying product usage data, CRM structure, and conversational intelligence into something actually actionable.  Plus, both Justin and Jessica geek out on the AI and vibe coding moment we're all living through and why it changes everything for revenue teams. Chapters [00:00] Intro & Jessica's Path to Canva Justin welcomes Jessica and she traces her journey from Melbourne to San Francisco, through Asana, and into Canva's B2B buildout. [02:57] Who Owns Onboarding and Time to Value? Jessica breaks down Canva's take on ownership across PLG and enterprise motions — and why success in the first hundred days is a team sport, not a CS problem. [05:57] Moving Upmarket: What Changes (and What Doesn't) From solo users with credit cards to C-suite transformations with change management — how Canva's onboarding approach shifts dramatically as deal size grows. [09:40] Using PLG Signals in an Enterprise World The Asana flashback: how rich end-user data and human relationship context can finally live in the same place, and what that unlocks for enterprise sellers. [11:47] The Tech Stack Behind the Motion CRM alone isn't enough. Jessica walks through how Canva combines structured CRM data, product usage signals, and a full conversational intelligence database to build a real picture of account health. [14:00] AI, Agents, and the Vibe Coding Moment Justin shares his own revelation using AI agents for GTM workflows, and Jessica drops that she recently vibe coded a weekly forecast interface. Neither of them is going back. [16:21] What's Ahead for Canva GTM in 2026 Canva Create in LA, platform updates Jessica can't fully share yet, and the team's focus on becoming the gold standard for enterprise go-to-market.

    20 min

  5. MAR 13

    The 10 AM Revolution: How AI is Transforming the Marketer's Day w/ Allison Skidmore, Chief Customer Officer at Optimizely

    Justin sits down with Allison Skidmore, Chief Customer Officer at Optimizely, the world's first operating system for marketing teams. Allison brings a rich perspective shaped by stints at Adobe, Stackla, Gigya, and SAP across Asia Pacific before landing in the US to lead customer success at Optimizely. This episode explores how AI is fundamentally reshaping the marketer's daily workflow, what great onboarding looks like in an AI-native world, and what the CCO role must become as organizations race to stay ahead. Episode Notes & Key Topics 1. Allison's Career Journey Started in SEM at a Sydney agency later acquired by Adobe, rode the wave of digital marketing's early SaaS transition.Spent six years at Adobe running customer success across Asia Pacific, building offshore teams and subscription services models.Moved through Stackla and Gigya (acquired by SAP nine months in), then scaled the CS role across all SAP lines of business in APAC.Joined Optimizely two years ago after reconnecting with CEO Alex Atzberger, bringing global enterprise CS experience to a fast-growing martech platform.2. What Stays the Same in Customer Success The sales-to-CS handover friction is timeless: it never goes away regardless of company size or stage.Digital-first customer engagement (email, offshore teams, automation) has been a constant scaling challenge for decades.The shift from time-and-materials professional services to subscription models remains a dominant trend.Tech advancements create the inflection points:  AI is today's example.3. AI and the Marketer's Day-in-the-Life Allison paints a vivid picture: by 10 AM, an AI-enabled marketer has completed a full week's worth of work.Optimizely's Opal AI product is provisioned across the entire team, enabling agent building, workflow automation, and access to tools like Claude and Gemini.The opportunity is not just efficiency, it's the ability to pull forward backlogged work and shrink implementation timelines (e.g., from 12 months to 3).The companies moving fastest are the ones blocking calendar time to train their teams on prompting and agent-building, not just giving access.4. Reimagining Onboarding and the Customer Journey Allison's framework: great onboarding is the seamless alignment of three channels, human-to-human touchpoints, email marketing, and in-product experience.Customers now expect to self-serve answers (just like asking AI instead of calling a mechanic), human-heavy onboarding alone no longer cuts it.Consistency is the key: the message the customer gets in the product, in their inbox, and from their CSM should be identical, no basic repeats, no skipped steps.5. The Evolving Role of the CCO The C-suite fundamentals don't change: stay curious, solve problems, skate to where the puck is going.Today, the puck is AI.  If you can't build an agent, you can't expect your team to.Allison is actively realigning roles, KPIs, and commissions around AI-native execution.The CCO who can't leverage AI to scale themselves and reimagine their business will become extinct, just like Blockbuster.Lego is the positive model: reinvention again and again.6. What's Top of Mind for 2026 AI continues to dominate, but the customer journey evolution is a close second.Consumers are shifting from Google to ChatGPT and similar tools, which means brands must optimize for GEO (Generative Engine Optimization), not just SEO.Personalization is entering a new era:  every touchpoint, not just the website.

    20 min

  6. FEB 27

    Retention Isn’t Dead. It’s Just Getting Smarter. Brent Krempges, Chief Customer Officer at Gainsight

    Brent Krempges, Chief Customer Officer at Gainsight, joins the show to unpack the next evolution of Customer Success in an AI-first world. After 12+ years at Gainsight, from implementation to global pre-sales to CCO,  Brent shares how CS is shifting from seat-based software to outcome-driven operating models. We dive into AI-driven health scores, renewal agents, sentiment analysis, and the looming “retention reckoning” facing AI-native companies.  Key Takeaways (Bullet Summary)AI will elevate — not eliminate — the importance of services.Floor-Deployed Engineers (FDEs) signal a return to high-touch value realization.Health scores are getting smarter, but “watermelon accounts” will always exist.Sentiment analysis from transcripts and email may replace traditional NPS.Many AI companies haven’t hit their renewal reality yet.Retention pressure is coming — especially for growth-at-all-costs AI startups.Before deploying agents, companies must rebuild foundational lifecycle processes.Think of agents as “50 interns” — would they know what to do?

    26 min

  7. FEB 13

    AI Didn’t Kill Premium Media. It Made It More Valuable. Elizabeth Herbst-Brady, CRO of Condé Nast

    In this episode of the Thread Podcast, Justin Vandehey sits down with Elizabeth Herbst-Brady, Chief Revenue Officer of Condé Nast, to explore how one of the world’s most iconic media companies is navigating transformation in the age of AI. Elizabeth shares lessons from her career spanning media, advertising, and technology, including leadership roles at Yahoo, Snap, and Viacom, and explains why trusted brands, human creativity, and editorial authority are becoming more valuable, not less, as AI accelerates content creation. The conversation covers how Condé Nast is using AI responsibly to enhance, not replace premium content, how revenue teams are being unified across advertising, commerce, subscriptions, and live events, and what it takes to lead teams through constant transformation with curiosity, accountability, and gratitude. This episode is a masterclass in modern GTM leadership at the intersection of creativity, technology, and trust. Chapters  00:00 – Welcome & Elizabeth’s Career Journey From media and entertainment to technology and back to Condé Nast. 04:40 – Why Condé Nast, Why Now The opportunity to lead revenue at an iconic, trust-driven brand. 07:30 – AI and the Future of Premium Content Why AI can’t replace human creativity, taste, and editorial authority. 11:45 – Creation vs. Curation in an AI World How Condé Nast separates content creation from AI-powered enhancement. 15:30 – Using AI to Improve Consumer Experience Real examples from Bon Appétit and The New Yorker. 19:30 – Why LLMs Reward Credibility Over Volume How AI changes the economics of SEO, expertise, and originality. 23:40 – Unifying Revenue Across Silos Bringing advertising, commerce, subscriptions, and events into one revenue org. 27:50 – Leading Through Transformation Elizabeth’s leadership framework: curiosity, accountability, and gratitude. 32:30 – What’s Next for Condé Nast & Premium Media Why trusted brands will accelerate over the next 12–24 months. Key Highlights & Takeaways AI should enhance content, not replace human voice or judgment.Trust, credibility, and editorial authority are premium assets in an AI era.LLMs reward expertise and originality, not volume or SEO tricks.Revenue transformation requires visibility, shared data, and cohesion across teams.The best leaders embrace constant change with curiosity and accountability.Premium media’s value proposition strengthens as information becomes noisier.

    24 min

  8. JAN 30

    Value Isn’t a Feature: Neal McCoy on Customer Success, AI, and the Post-Sale Moment That Matters

    In this episode of the Thread Podcast, host Justin Vandehey sits down with Neal McCoy, VP of Customer Success and Professional Services at BigCommerce, to unpack where customer value most often breaks down after a deal is closed — and how companies can fix it. Neal shares insights from nearly a decade building CS and PS at BigCommerce, explaining why customers don’t buy software to “solve problems,” but to make or save money. The conversation explores how unclear value realization creates friction during onboarding, why sales-to-CS handoffs fail, and how AI is reshaping customer success through better context, automation, and voice-of-the-customer insights at scale.  Key Takeaways & Highlights Customers buy software to make money, save money, or both — not just to solve surface-level problemsMisalignment on value realization is the #1 reason onboarding and CS struggle post-saleSales teams often assume customers understand value — they usually don’tThe earlier value is quantified and documented in the sales cycle, the stronger the post-sale executionAI can eliminate manual handoff friction by summarizing calls, emails, and deal context automaticallyTraditional CS metrics like surveys and NPS are statistically weak; voice of the customer at scale is the futureCustomer success leaders must act as the primary conduit for customer insight back into product and GTMPersonalization at scale requires cohort-based learning, not one-size-fits-all onboardingFewer deals with clearer value often outperform higher-volume pipelines long termThe best salespeople optimize for customer outcomes, not just closed deals Chapters & Timestamps 00:00 – Welcome & Introduction Justin introduces Neal McCoy and his background across military, fintech, digital engagement, and ecommerce. 02:00 – Neal’s Career Path & BigCommerce Journey How Neal helped build CS and professional services as BigCommerce moved upmarket. 04:30 – Where Customer Value Breaks Down Post-Sale Why customers trade one set of problems for another when value isn’t clearly defined. 06:45 – What CS Wishes Sales Would Hand Off (But Rarely Does) The missing context that makes or breaks onboarding and adoption. 09:15 – AI’s Role in Fixing the Sales-to-CS Handoff How AI can summarize deal context and remove the burden from sellers. 11:45 – Voice of the Customer vs. Traditional CS Metrics Why surveys fail and how AI unlocks insight from unstructured customer data. 14:30 – Personalization at Scale in Ecommerce Onboarding Using cohort-based success models across industries, regions, and merchant types. 17:15 – The Biggest Misconception Sales Leaders Have About Post-Sale Why focusing on value may reduce conversions but increase long-term growth. 20:00 – The Future of CS, PS, and AI at BigCommerce How AI is changing delivery models, expertise, and customer expectations. 22:30 – Closing Thoughts & What’s Next Neal’s outlook on AI, value delivery, and helping merchants succeed long-term.

    24 min
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About

The Thread Podcast explores the future of enterprise sales in the era of AI.  Hosted by Justin Vandehey, founder of Thread, we bring together top sales leaders, enablement pros, and innovators shaping how go-to-market teams grow and win. Each episode dives deep into what’s changing in sales—from real-time AI coaching to modern revenue systems of action—and features actionable insights from CROs, RevOps leaders, startup founders, and the technologists building the next generation of tools. Whether you’re scaling founder-led sales or leading a global GTM team, you’ll walk away with new strategies to improve seller performance, accelerate deal cycles, and leverage AI for growth. If you’re ready to think differently about sales execution and the future of GTM, follow The Thread and join the conversation.

Information

  • Creator
    Justin Vandehey
  • Years Active
    2022 - 2026
  • Episodes
    152
  • Rating
    Clean
  • Copyright
    © 2026 The Thread Podcast
  • Show Website
    The Thread Podcast