Episodes

  • Tackling new territories, multi-threading, and more with Krysten Conner

    Tackling new territories, multi-threading, and more with Krysten Conner
    Aug 31 2026
    In this episode, Jason and Krysten Conner, sales coach at krystenconner.com, talk about the where-we-win report every new AE should run, the ship jumper move and other warm-path openers, ghost-writing a referral email your champion will send, and running EMT discovery on outbound-led calls. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 13 mins
  • The Too Good To Ignore Outbound Methodology

    The Too Good To Ignore Outbound Methodology
    Aug 24 2026
    In this episode, Jason, Clara Johnson, and Amanda Long from Outbound Squad, talk about why outbound needs its own methodology, the three core parts of Too Good To Ignore, how to scale it across your team, and practical plays your reps can use to book more meetings. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 11 mins
  • Meet Amanda Long, our newest Pipeline Consultant

    Meet Amanda Long, our newest Pipeline Consultant
    Aug 17 2026
    In this episode, Jason and Amanda Long from Outbound Squad, talk about the daily practice ritual that took her to the top of the leaderboard, how she made it impossible for her manager not to promote her, and how to nail your first front-line leadership role. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 7 mins
  • 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