Episodes

  • Mental health and finding fulfillment in sales with Alex Kremer

    Mental health and finding fulfillment in sales with Alex Kremer
    Sep 28 2026
    In this episode, Jason and Alex Kremer from Alluviance, talk about why 70% of sales pros are struggling with their mental health, the two wells analogy and the hungry ghost trap, rewiring where your motivation comes from, and selling from presence, not pressure. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 13 mins
  • Lessons from a first-time sales manager

    Lessons from a first-time sales manager
    Sep 14 2026
    In this episode, Jason and Matt Rogers from Neo4j, talk about breaking into a cold enterprise territory in person, the monthly accountability one-on-one to run with every rep, the hero move that traps first-time leaders, and using AI to scale coaching without watching every call. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 17 mins
  • Building an AI-native sales motion with Heath Barnett

    Building an AI-native sales motion with Heath Barnett
    Sep 7 2026
    In this episode, Jason and Heath Barnett, formerly of Mixmax, talk about why PLG and product-led sales aren't the same thing, the three layers of a real ICP, account scoring with sub-scores that stack, and why AI investment flops without rep skill investment. Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠
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    1 hr and 7 mins
  • 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