Stop Just “Checking In” and Start Creating Milestone Moments with Customers | Jason Bradwell, Founder of B2B Better and Host of Pipe Dream Podcast

Episode notes

This episode is brought to you by B2B Better. Stop sending "just checking in" emails. We build owned media systems that give your sales team actual reasons to reach out, turning podcasts into sales enablement assets that move deals forward. If your sales reps send "just checking in" emails to prospects who've gone quiet, this episode explains why those fail and what to do instead. Host Jason Bradwell breaks down how to create milestone moments, legitimate, value-led reasons to reach out through long sales cycles without sounding desperate. Jason's core point is clear: most B2B sales cycles are brutally long, but sales teams don't know how to stay present without being annoying. The traditional approach fails. Discovery call, proposal sent, then "just checking in" emails with no response. Twelve months later, the prospect went with a competitor because "you didn't understand our business." After month two, you had nothing valuable to say. 95% of B2B Better's clients have sales cycles over six months. And 95% of your customers are out of market at any given time. Your job is to stay present so when they flip to being in market, they think of you first.

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