Volume 342, Issue 2 · 8 articles
Sales culture is obsessed with the new. New logos, new prospects, net-new pipeline. And that hunt matters. But it quietly overshadows a truth every experienced IT seller eventually learns: the richest, most efficient pipeline you have is sitting inside your existing customer base. These are people who already trust you, already pay you, and already know your solution works. Expanding and renewing them is dramatically easier than winning a stranger - and yet most reps put almost no deliberate effort into staying meaningfully present with the customers they already have. Read more
Every sales professional has done it, and every sales professional secretly hates doing it. The deal has gone quiet. You need to re-engage. You have nothing new to say. So you type the four most defeated words in sales - "just checking in" - dress them up with a little padding, and hit send, knowing the prospect will see straight through it. These messages rarely work, because they broadcast the truth: you're reaching out for your benefit, not theirs, and you have no real reason to be in their inbox. Read more
Every seasoned IT sales professional has a drawer, a spreadsheet, or a CRM full of contacts collected over years - business cards from conferences, badge scans from trade shows, connections from a dozen jobs and campaigns. It feels like an asset. It mostly isn't. Those contacts decay quietly the moment you file them away: people change roles, switch companies, and forget who you are. A name in a database you never touch is not a relationship. It's a fossil. Read more
There are two ways to fill a pipeline. You can hunt - cold calls, cold emails, list-buying, sequences, and the grinding math of low reply rates. Or you can build something that attracts buyers to you, so that some meaningful share of your pipeline arrives already interested. Most IT sales professionals live almost entirely in the first world. The second world feels like it belongs to marketing, or to influencers, or to somebody with more time. It doesn't. A LinkedIn newsletter puts it within reach of any individual rep. Read more
There are two ways to fill a pipeline. You can hunt - cold calls, cold emails, list-buying, sequences, and the grinding math of low reply rates. Or you can build something that attracts buyers to you, so that some meaningful share of your pipeline arrives already interested. Most IT sales professionals live almost entirely in the first world. The second world feels like it belongs to marketing, or to influencers, or to somebody with more time. It doesn't. A LinkedIn newsletter puts it within reach of any individual rep. Read more
Cold outreach has a fundamental problem, and it isn't your subject line, your opener, or your call-to-action. It's that the person on the other end has no reason to believe you're worth their time. You're a stranger asking for something. Every optimization tactic in the world - personalization tokens, pattern interrupts, clever hooks - is really just an attempt to compensate for that one deficit: the absence of any prior relationship or credibility. Read more
Ask any enterprise IT buyer how they feel about salespeople and you'll get a tired sigh. It's not personal. It's the accumulated weight of a thousand cold emails, a hundred "quick calls," and an inbox full of reps who all somehow have "a solution that's perfect for your exact challenges" despite never having spoken to them. To the average buyer, the word vendor has come to mean someone who wants my money. Read more
Every enterprise IT sales professional knows the rhythm of a deal. There's the discovery call, the demo, the proposal, the negotiation - a handful of high-stakes conversations spread across weeks or months. We prepare obsessively for those moments. We rehearse objection handling, tune our slides, and study the org chart. And then, between those moments, we go quiet. Read more