The Thread Podcast

Justin Vandehey
  • 5.0 (15)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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. 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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 12/27/2025

    Growing Up with RevOps: 13 Years Inside Integrate with Jared Myatt, RevOps at Integrate

    In this episode of the Thread Podcast, Justin Vandehey sits down with Jared Myatt, Senior Director of Revenue Operations at Integrate, to explore what it really takes to scale RevOps over time. Jared shares his journey from early employee to RevOps leader, reflecting on key inflection points including acquisitions, private equity ownership, and enterprise growth. They discuss how the definition of RevOps has evolved, why data must power decision-making (not just dashboards), how culture scales through honesty and curiosity, and why alignment across GTM teams ultimately comes down to communication—not tools. This is a must-listen for anyone building RevOps in a growing SaaS organization. Key Topics Covered Growing with a company from early startup to enterpriseWhat RevOps actually is (and what it isn’t)Using data to tell real revenue storiesScaling culture without over-engineering itCareer advice for aspiring RevOps leadersWhy alignment breaks—and how to fix itThe role of RevOps as GTM problem solversSuggested Chapters 00:00 – Welcome + Jared’s background  02:30 – Early ownership and pivotal moments at Integrate  04:30 – How RevOps has evolved over the years  06:00 – Using data to tell the revenue story  07:45 – Preserving culture through growth  10:45 – Career advice for moving into RevOps  13:30 – What alignment really looks like  16:45 – Integrate overview + closing

    23 min

  8. 12/19/2025

    Equity Is a Revenue Lever: Benjamin Roach on RevOps in the Incentives Economy

    In this episode of the Thread Podcast, Justin Vandehey interviews Benjamin Roach, Director of Revenue Operations at Optio Incentives, to explore what it takes to build RevOps in the equity compensation and incentives space. Ben shares his “traditional” path from sales into RevOps, why he deliberately took a step back into a junior ops role, and how getting technical became a career unlock. They dig into the complexities of selling and operating in equity management—where revenue can include ARR, transactional fees, and services, and where buyers span CFOs, CHROs, legal, and finance. Ben also shares his point of view on AI: where it can help participants and admins get fast answers, and why data quality and human oversight still matter. The episode closes with career advice for aspiring RevOps leaders and how to learn the craft. Key topics covered Why Ben moved from sales → RevOps (and why he “took a step back” to level up)Equity compensation complexity: strike price, taxes, vesting, global complianceHow Optio’s GTM motion sells “trusted partner + tech,” not just softwareMeasuring growth in equity management beyond traditional ARRAI in equity management: where it’s useful today and where it’s riskyCareer advice: become technical, stay curious, build a broader toolbelt Memorable moments / quotable lines “Stock options… were unknown to me. You get handed them and think, maybe one day I’ll make money.”“AI is only as good as your data models.”“Don’t be scared to take a step backwards.”“RevOps wears so many hats—you need a lot of tools on your toolbelt.”Chapters (suggested) 00:00 – Welcome + Ben’s intro  01:00 – From sales to RevOps (and why he took a step back)  02:10 – Why the equity/incentives space pulled him in  03:30 – Aligning finance, HR, and revenue metrics  04:45 – Why revenue isn’t just ARR in equity management  05:30 – Simplifying a complex story for CFOs/CHROs/legal  06:55 – Global compliance + product readiness constraints  09:00 – AI in equity: what it can and can’t do (yet)  11:05 – Career advice for aspiring RevOps leaders  13:45 – Plug: Optio + how to connect with Ben

    19 min
See All (150)

5
out of 5
15 Ratings

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
    150
  • Rating
    Clean
  • Copyright
    © 2026 The Thread Podcast
  • Show Website
    The Thread Podcast