Outbound Squad

In this episode, Jason and Rippling’s Senior SDR Director, Bert Brokaw, talk about what it really takes to crush the Director of SDR role, from leading managers and aligning with executives to building a high-performing outbound culture. Tune in to learn how top leaders grow strategic SDR teams that consistently deliver results.

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Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Jason talks about why sales leaders must partner with enablement to drive real culture change and shares three lessons from top teams—becoming a trusted advisor, sharing the stage with reps, and prioritizing manager enablement over rep-only training.

Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.

In this episode, Jason breaks down why AI isn’t replacing SDRs anytime soon, sharing real hiring data from leading AI companies and explaining why human reps who learn to leverage AI will outperform, not be replaced by it.

Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Jason was a guest on the Outbound Kitchen - Sales Podcast hosted by Elric Legloire to share tactical cold-calling frameworks—using permission-based openers, problem-focused language, and compelling offers to boost connect rates, spark real interest, and book meetings that actually show up.

Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

In this episode, Aaron Rissler shares his journey from IC to VP of Sales at Buyer's Edge Platform, revealing the lessons, strategies, and leadership insights he’s learned along the way to build high-performing teams, navigate corporate politics, and level up at every stage of a sales career.

Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠