『NC Tweener Talks』のカバーアート

NC Tweener Talks

NC Tweener Talks

著者： NC Tweener Fund
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A podcast for builders by builders in North Carolina. We explore the startup journey and stories with NC founders, from the idea to the exit and everything in between. NC Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West.2026 NC Tweener Fund マネジメント・リーダーシップ リーダーシップ 個人ファイナンス 経済学
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  • Jesse Lipson, CEO & Founder of Levitate: Building AI Features Won't Save You but Here's What Will

    Jesse Lipson, CEO & Founder of Levitate: Building AI Features Won't Save You but Here's What Will
    2026/06/25

    Jess Lipson, founder and CEO of Levitate, joins host Scot Wingo for a focused, framework-driven conversation on how SaaS founders should think about their businesses in the age of AI. Jess has been building SaaS since before the category had a name. His first company, ShareFile, sold to Citrix and eventually became a billion-dollar business. At Citrix, he ran the company's entire SaaS portfolio. Now at Levitate, a relationship marketing platform serving nearly 9,000 small businesses, he's spent the last year working out a clear-eyed answer to one of the most common questions Scot hears from Triangle founders: what do you actually do about the SaaSpocalypse? In this episode, Jess introduces two tests every SaaS founder should run: the Removal Test (if you strip AI out of your product, does it still function?) and the Growth Re-acceleration Test (is your growth rate going up or down, and what does that signal to investors?). Scot adds a third indicator from what he's seeing across the Tweener Fund portfolio: churn driven by customers who are now vibe-coding their own replacements. Together, they walk through how the buy-vs.-build equation has shifted 10 to 100 times, why having AI features is now table stakes rather than a competitive advantage, and what it looks like to build a business where new frontier model releases feel like tailwinds instead of threats.

    Timestamps
    00:00 Cold Open & Welcome

    00:29 Sponsors: Robinson Bradshaw & Bank of America

    01:24 Scot's Intro: The SaaSpocalypse

    02:31 The February Tweener Times Piece

    03:05 Why This Episode Exists

    04:08 Welcome Jess Lipson

    04:37 How Scot & Jess Know Each Other

    05:10 Jess's SaaS Pedigree: ShareFile to Citrix

    05:49 SaaS Multiples Have Collapsed

    07:00 Salesforce, HubSpot & Workday Are Down Too

    08:13 AI Features Are Table Stakes

    09:50 Is This the Lowest SaaS Multiples Ever?

    11:28 Investment Landscape: Subscale SaaS Is Struggling

    12:23 Framework #1: The Removal Test

    14:22 Framework #2: Growth Re-Acceleration

    15:23 Scot's Third Signal: Vibe Coding Churn

    17:32 The Buy-vs.-Build Equation Has Shifted 10–100X

    19:29 When Claude Becomes Your "Single Pane of Glass"

    19:44 MCP Servers & Levitate's API Revamp

    21:50 How Levitate Is Passing Its Own Tests

    22:31 New Offering: Helping SMBs Actually Implement AI

    23:44 Software + Services as the Durable Model

    24:11 The Fear Index: Do You Dread New AI Releases?

    24:50 Raleigh Founded & Closing Thanks

    25:04 Outro


    -----


    Where to Find Jesse Lipson:
    LinkedIn: https://www.linkedin.com/in/jesse-lipson-625195/
    Levitate Ai: https://www.levitate.ai/

    Where to Find Scot Wingo:
    LinkedIn: https://www.linkedin.com/in/thescotwingo/
    Tweener Times: https://www.tweenertimes.com/
    X: https://x.com/scotwingo

    ---

    This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West.

    We couldn’t share posts like this without our amazing sponsors:

    Platinum:
    NC IDEA: https://ncidea.org

    Gold Sponsors:
    - Balentine: https://www.balentine.com/triangle-entrepreneurs
    - EisnerAmpner: https://www.eisneramper.com
    - Robinson Bradshaw: https://www.robinsonbradshaw.com

    Silver Sponsors:
    - Automated Consulting Group: https://automated.co
    - Bank of America: https://business.bofa.com/en-us/content/technology-industry-group.html


    ------
    Triangle Tweener Talks is sponsored by:

    • Atomic Object: https://atomicobject.com/
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    26 分
  • FLASH: Validic (NC Tweener!) acquired by ChartSpan - Live Interview with Drew Schiller, CEO, Validic

    FLASH: Validic (NC Tweener!) acquired by ChartSpan - Live Interview with Drew Schiller, CEO, Validic
    2026/06/22

    Details->https://www.tweenertimes.com/p/breaking-validic-acquired-by-chartspan

    We couldn’t share posts like this without our amazing sponsors:

    Platinum:
    NC IDEA: https://ncidea.org

    Gold Sponsors:
    - Balentine: https://www.balentine.com/triangle-entrepreneurs
    - EisnerAmpner: https://www.eisneramper.com
    - Robinson Bradshaw: https://www.robinsonbradshaw.com

    Silver Sponsors:
    - Automated Consulting Group: https://automated.co
    - Bank of America: https://business.bofa.com/en-us/content/technology-industry-group.html


    -----


    Where to Find xxxxxx:
    LinkedIn: xxxx
    Front Porch Venture Partners xxxx

    Where to Find Scot Wingo:
    LinkedIn: https://www.linkedin.com/in/thescotwingo/
    Tweener Times: https://www.tweenertimes.com/
    X: https://x.com/scotwingo

    ---

    This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West.

    We couldn’t share posts like this without our amazing sponsors:

    Platinum:
    NC IDEA: https://ncidea.org

    Gold Sponsors:
    - Balentine: https://www.balentine.com/triangle-entrepreneurs
    - EisnerAmpner: https://www.eisneramper.com
    - Robinson Bradshaw: https://www.robinsonbradshaw.com

    Silver Sponsors:
    - Automated Consulting Group: https://automated.co
    - Bank of America: https://business.bofa.com/en-us/content/technology-industry-group.html


    ------
    Triangle Tweener Talks is sponsored by:

    • Atomic Object: https://atomicobject.com/
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    16 分
  • Rob Walter, Founder & CEO of RevBo: "Nobody Has It Right; The GTM Playbook Is Still Being Written"

    Rob Walter, Founder & CEO of RevBo: "Nobody Has It Right; The GTM Playbook Is Still Being Written"
    2026/06/18
    Rob Walter breaks down the AI-native GTM playbook: intent data, ABM-only outreach, the first sales hire trapdoor, and why "a human always writes the message." Stick around for the highlights below. 👇Highlights"Nobody has it right: Rob's honest take on the current AI-GTM moment; the playbook is genuinely still being written, adoption is wildly uneven, and that gap between the leading edge and everyone else is the opportunity. Carpet bombing is killing brands: AI has made outbound spam so cheap and easy that it's destroying trust at scale. One competitor even cold-emailed Scot about "agentic commerce", not realizing they were emailing a direct rival. Rob's rule: "A human always writes the message." AI-generated outreach is detectable, and it permanently trains your ICPs to ignore you. Intent data, explained:Website visits, job postings, funding announcements, keyword searches, these are the signals that tell you when to reach out and why. Rob describes it as a "spider on a web" with legs out, waiting for any ICP company to show a flicker of intent before timing a precise, relevant outreach. He used actively.ai (recently raised its Series B) at BigCommerce, standing up the POC in about 2 months. ABM is now nearly the only outreach strategy: AI removed the bandwidth bottleneck that always made true account-based marketing impractical. Rob's view: from a direct outreach standpoint, it's now "darn close to ABM only." The first sales hire trapdoor: "Never hire someone from a big company and think they're gonna do well in your startup as a first sales employee. Never. I have never seen that work. Hundred percent failure rate." Their first question is about PTO policy and whether they get an admin. Four tiers of salespeople: Great and good reps will get dramatically better with AI. The "meh" tier, people who got by on volume and the occasional lucky close, will get weeded out. Founders need to know this when evaluating candidates. GTM engineer > first sales rep: A GTM engineer who can automate enrichment, workflow, and outreach sequencing can be "far more powerful than, honestly, maybe even a sales rep in some cases" for early-stage companies. Rob says this is one of his most consistent recommendations to founder-led businesses. Granola over Gong: For companies under $10M ARR, Rob's call recording recommendation is Granola, it works in coffee meetings, integrates cleanly with Claude for analysis, and costs a fraction of what Gong does. He uses it himself, with a custom recipe that pulls prospect questions across all sales calls and runs them through Claude to bucketize and rank by frequency, then puts that content directly on the website.The data model rule: If you don't capture milestone moments in your CRM now, first discovery call, account enrichment data, stage exit criteria, that information is "gold dust that slipped through your fingers." Nothing AI can do later will recover it.SaaSageddon is real: Buyers are hesitating on new software contracts. Rob's framework: for narrow use cases, try to build it before you buy it. For compliance-heavy enterprise environments, you probably still buy. And there are now AI-native alternatives (he uses Clarify AI for CRM) worth considering over legacy incumbents. The RevBo scorecard: Rob built a free AI-native GTM diagnostic at revbo.ai, it walks companies through ICP clarity, data model hygiene, and intent/enrichment readiness before recommending any tooling. A good starting point before any of the tools in this episode make sense.Rob has been in the rooms where SaaS was built, scaled, and now, in some ways, disrupted. Every piece of advice in this episode comes from having actually done the thing, not just advised on it. Enjoy the conversation.Timestamps:00:00 Cold Open 00:40 Welcome to NC Tweener Talks 01:55 Episode intro 02:22 How Scot knows Rob 04:28 Rob's background05:45 Coming to North Carolina 07:55 Rob at ChannelAdvisor 09:04 Evolution of SaaS GTM roles 12:44 GTM in the pre-AI era 14:00 CRO at BigCommerce 17:15 Modernizing the stack with AI 19:52 The carpet bombing problem22:00 Rob's rule #1:22:55 Intent data explained24:50 Modern intent signals 26:03 Inbound content strategy29:26 Clay, Apollo & enrichment 31:25 ABM 32:44 Rob leaves Commerce and starts RevBo 34:20 Who Rob works with 37:00 The first sales hire trapdoor39:55 The RevBo scorecard 41:55 Call recording 44:30 AI agents 46:02 SaaSageddon49:37 GTM engineering 50:52 Wrap-up Where to Find Rob:LinkedIn: https://www.linkedin.com/in/rob-walter/RevBo AI: https://revbo.ai/Where to Find Scot Wingo:LinkedIn: https://www.linkedin.com/in/thescotwingo/Tweener Times: https://www.tweenertimes.com/X: https://x.com/scotwingo--- This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by NC Tweener Fund, with creative assets and design support from Walk West. We couldn’t share posts like this without our amazing sponsors: Platinum: NC IDEA: https://...
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    52 分
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