Did we make selling easier and buying worse?
About the episode
We’ve spent nearly two decades trying to make selling easier, CRMs, automation, sequences, intent data, and now AI. So why does it feel harder than ever to actually earn a buyer’s trust? Jen Allen-Knuth, founder of DemandJen, joins Rachel Truair to explore whether sales technology was ever really built for the buyer, or whether it mostly optimized the seller’s side of the interaction. Jen makes the case that “personalization” has become one of the emptiest words in sales, breaks down what actually makes a cold email work, and gives her honest read on whether the sales profession shrinks as AI takes over research and outreach.
The question underneath it all: if every piece of sales technology disappeared tomorrow, what would still make one human worth talking to?
“ Personalization has been one of the worst terms to ever come out of sales or marketing because it's not specific enough to mean anything. ”
Founder of DemandJen
“ I think if we continue on as we have, there is going to be a much smaller number of people that are gonna sit in a sales profession. ”
Founder of DemandJen
“ In sales, the hard work works because it's hard. Most people choose easy. ”
Founder of DemandJen
From the conversation
- Why so much of sales technology has been built to optimize the seller’s side of the interaction, not the buyer’s
- Why “personalization” has become one of the emptiest words in sales and marketing, and what real relevance looks like instead
- What separates a cold email that gets a reply from the hundreds that get ignored
- Whether the sales profession shrinks as AI takes over research, writing, and outreach, and where a human still earns their seat at the table
- Why customer stories are sales’ most underused asset, buried in an LMS while reps lean on self-congratulatory slides
About the guest
Jen is the founder of DemandJen, a sales training and consulting company focused on helping GTM teams break through the status quo and avoid losing pipeline to buyer risk aversion. As a keynote speaker and sales trainer, she specializes in equipping sales teams selling into enterprise and mid-market with the tools to overcome customer hesitation and close more deals. Jen brings in-depth strategies to help teams confront the fear of change and risk, and she’s a go-to for sales kickoffs and workshops that drive success.
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