“If you want a sales pipeline, you are responsible for creating it. What we've been told and what we see online is the kind of constant content creation that is designed to bring you clients…so that you can essentially do a lot of marketing to avoid ever having the sales conversation.

But the quickest way to make a sale though is to get to that sales conversation as soon as you can and to make sure that it's as qualified as possible."

Most of us have been on the receiving end of a terrible cold pitch. Maybe it was a LinkedIn DM pretending to be friendly. Maybe it was an email that made you feel like a number. No surprise—cold outreach has earned its bad reputation.

But the truth is: cold outreach isn’t inherently bad. It’s just rarely done well.

In this episode of Aggressively Human, we’re joined by sales strategist Jessica Lorimer, who got her start in the kind of sales that makes people sweat: actual phone calls, to actual humans, in actual corporate offices. We talk about what it looks like to sell in a way that’s clear, kind, and effective—without relying on funnels, fake rapport, or endless social media content. She breaks down what still works, what definitely doesn’t, and how to sell in a way that’s honest, respectful, and doesn’t make you feel like a spammer.

This episode is part strategy, part sales therapy, and part reminder that you’re allowed to enjoy sales.

* Jessica’s origin story: how she sold her way into a boardroom (without a formal invite)

* How “being good at sales” actually made Jess feel in the early days of running an online business, and why she shifted from B2C to B2B sales

* Why Jess and Meg have both gotten rid of their funnels

* The five-step B2B sales framework Jess uses with her corporate clients (and why it works for soloists too)

* Why “I sent 10 emails and no one replied” isn’t a valid reason to give up

* What you actually need in a cold message (spoiler: not a fake compliment or a pitch)

* Why it’s not about “convincing” someone to buy—it’s about showing them it’s worth a conversation

* And why selling isn’t about tricking anyone—it’s about being clear, useful, and brave enough to go first

About our Guest

Jess Lorimer | LinkedIn

Selling to Corporate Podcast - a bi-weekly favorite of Jessica Lackey’s!

From Cold to Closed - open through May 18!

Connect with Us

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Connect with Meg and Jessica

Meg Casebolt

Jessica Lackey

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

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