“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. When we talk about lead generation, you can create content for months and you might not actually hit upon the right people. Even if you go viral, you might end up on the wrong side of the ‘gram or, or whatever the cool kids are calling it, and then suddenly have hundreds of comments about your personality in instead of your service.
What we look at in new business development is how can we get to the decision maker as quickly as possible? How can we let them understand that we actually want to have a relevant conversation?” - Jess Lorimer
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
“What we're not doing is saying, ‘You should have a call with me. I can fix your SEO because your website's terrible, or whatever else is going on.’ You are saying to people, “‘Here's the commercial benefit of spending time with me. I've thought about what's going on with your business and why it would be relevant for me to reach out to you right now.’ So what that person is not hearing is a 10 minute pitch on SEO. They're hearing, oh yeah. No, I'd not thought that I hadn't got as many inbound inquiries as I have in the past. Oh, I should do something about that. Yeah, let's have a chat.
It's not pitching. It's how can we get on a call and talk about what you might want to do?” - Jess Lorimer
About our Guest
Selling to Corporate Podcast - a bi-weekly favorite of Jessica Lackey’s!
From Cold to Closed - open through May 18!
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