
In this episode, Jason and Scott Leese from Scott Leese Consulting, talk about building a career and income that don't depend on any one job. They dig into why personal brand might be the last career moat, when to start earning outside your W2, his 10-a-day plan for growing your network, and how he builds his calendar around family time.
Check out more free content and get help with outbound at https://outboundsquad.com.
Oct 12
1 hr 14 min

In this episode, Jason and Ryan Heaphy from Fractal Software, talk about what it takes to build a repeatable sales motion in early-stage vertical SaaS. They dig into why the VP of Sales hire usually flops, what a world-class sales playbook actually includes, reverse-engineering quota from pipeline, and what cold calling looks like in vertical SaaS.
Check out more free content and get help with outbound at https://outboundsquad.com.
Oct 5
1 hr 17 min

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.
Sep 28
1 hr 13 min

In this episode, Jason and Brandon Jackson, formerly of Common Room and now at Ping Identity, talk about his four-pillar CPAD framework for SDR leadership, why dial counts aren't the real measure of a good day, aligning SDR with marketing and sales at once, and where AI belongs in the SDR workflow, and where it doesn't.
Check out more free content and get help with outbound at https://outboundsquad.com.
Sep 21
54 min

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.
Sep 14
1 hr 17 min

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.
Sep 7
1 hr 6 min

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.
Aug 31
1 hr 12 min

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.
Aug 24
1 hr 11 min

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.
Aug 17
1 hr 6 min

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.
Aug 10
1 hr 6 min
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