Episodes

  • VP of Revenue at AdRoll on empathy, accountability, pipegen, and more

    VP of Revenue at AdRoll on empathy, accountability, pipegen, and more
    Aug 10 2026
    In this episode, Jason and Mark Haas from AdRoll, talk about why the top rep is often the worst first-time manager, his journey from programmer to rep to VP, and how he runs his day-to-day leading revenue. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 6 mins
  • Founding AE at 30 Minutes To President’s Club, Alex Murphy

    Founding AE at 30 Minutes To President’s Club, Alex Murphy
    Aug 3 2026
    In this episode, Jason and Alex Murphy from 30 Minutes to President's Club, talk about cold calling without the telemarketer feel, the offering mindset that keeps your self-worth out of the outcome, and his 3-question discovery checklist for first calls. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 21 mins
  • CRO of Orum on AI, cold calling, and the future of SaaS

    CRO of Orum on AI, cold calling, and the future of SaaS
    Jul 27 2026
    In this episode, Jason and John Eitel from Orum, talk about why top sales teams admit they haven't cracked AI, how to centralize AI through RevOps without hurting rep productivity, why skill still beats tool stack, and the pipegen mix by segment that holds up from high velocity to enterprise. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 13 mins
  • Scaling Rippling’s 400+ BDR org with Ashley Kelly

    Scaling Rippling’s 400+ BDR org with Ashley Kelly
    Jul 20 2026
    In this episode, Jason and Ashley Kelly from Rippling, talk about how Rippling scaled from 40 to 400 BDRs in under four years, the "go and see" value that runs from Parker on down, and the SDR-to-CRO program that keeps reps around. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 6 mins
  • From rep to manager to leading global enablement at Shopify with Siobhan Sweeney

    From rep to manager to leading global enablement at Shopify with Siobhan Sweeney
    Jul 13 2026
    In this episode, Jason and Siobhan Sweeney, formerly of Shopify, talk about her journey from door-to-door sales rep in New York City to first-time sales leader, why she made the jump into enablement, how Shopify built a world-class enablement org, and her take on executive presence, managing up, and coaching reps. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 1 min
  • Too Good To Ignore

    Too Good To Ignore
    Jul 6 2026
    In this episode, Jason guests on The Revenue Insiders to talk about Outbound Squad's Too Good To Ignore outbound methodology and its three pillars (disqualify, offer, provoke), the trigger, tension, trust messaging model that works across cold call, email, and social, and what it actually takes to build pipeline in 2026. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    44 mins
  • Tito Bohrt on building a world-class sales development org

    Tito Bohrt on building a world-class sales development org
    Jun 29 2026
    In this episode, Jason and Tito Bohrt from AltiSales, talk about his 4-part framework for building and diagnosing sales orgs, what's working in cold calling right now, and whether the SDR function is about to get replaced. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    51 mins
  • Motive CRO on moving up-market and leading an org of 3,000+

    Motive CRO on moving up-market and leading an org of 3,000+
    Jun 22 2026
    In this episode, Jason and Adam Block from Motive, talk about why they made the move up market, how they protected the mid-market and SMB business that was already working, how they rewired the culture for outbound, and the talent and metrics that matter when you're leading a 3,000-plus revenue org. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    56 mins