Ep 206: Prospecting That Actually Feels Natural with Jenna Deyle

Send us Fan Mail Sales envy is real. You watch someone effortlessly book meetings, build relationships, and “just know what to say,” while you stare at a blank LinkedIn message and wonder if you are cut out for this. I sit down with sales coach Jenna Deyle to prove that selling is not a personality trait, it is a system. And the best systems fit into your real life: busy weeks, client work, and the constant fight to keep your pipeline from shrinking. We get clear on what prospecting actually means, how it differs from marketing, and why cold outreach is only one slice of the work. Jenna walks through her practical LinkedIn-first approach, including when to send a connection request with no note, how to open with something personal that earns a reply, and why most B2B sales outreach needs about seven touches across channels before a prospect is ready to meet. We also talk warm outreach cadence, how to treat a fast “no” as a win, and how to lead with value using trigger events like Google News alerts, role changes, seasonal planning cycles, and simple shared context. Then we go full workflow nerd in the best way: exporting your LinkedIn network, using Claude to prioritize leads, multithreading inside an account, and building a simple CRM in Notion that you barely have to open. Jenna explains how she logs outreach quickly, runs a weekly review, and pushes follow-ups into Todoist so nothing falls through the cracks. If you want better B2B prospecting, stronger pipeline management, and a repeatable sales cadence that feels human, this conversation delivers. Subscribe for more practical marketing and sales systems, share this with a friend who hates outreach, and leave a review so more founders can find the show. What part of your prospecting workflow do you want to simplify first? Support the show Schedule a Booked-out Blueprint >>> *Schedule.* Come tour my digital home :) >>>*Website* Wanna be friends? >>> *LinkedIn* Let's chat every Tuesday! >>> *Newsletter* Catch the video podcast on YouTube *>>>**YouTube* Join my event group for live events >>>*Meetup*