The Future of Sales

Early in my career, I knew exactly when to call a decision maker.

You phoned before their admin arrived, in that window when the person was at their desk with a coffee, and no gatekeeper, and they picked up their own phone. If you were lucky, you’d get five maybe ten focused minutes.

That was it, that was the whole strategy, and it worked because the channel was uncluttered.

I remember the creatives and agencies who wanted my business sending things to my office. One of them mailed me an expensive bottle of booze and a shot glass etched with his name and one line: “Your best shot.” To this day, I still remember his name. An agency sent a proposal in a round package, a sphere instead of a box, with a note that said: “ We think out of the box.” The damn thing physically would not stay on my desk full of square envelopes. I had to constantly reposition it to keep it from rolling off.

In those times, deals got done primarily IRL. It’s odd now to imagine that business happened with two people in front of each other. None of this was as efficient as sending something virtually or hopping on a Zoom, and that was the point. Reaching a person took thought, effort, and sometimes a little imagination, and the effort itself was the message. It said I picked you.

Somewhere along the way, we decided that was too slow.

The tools and the data got cheap, and suddenly you could reach 10,000 people for the price of reaching 1, and everyone did. The logic was irresistible on a spreadsheet, especially for an agency owner struggling for leads. If a 1% response rate is fixed, then more sends means more deals, so the game became volume. Every founder, every agency, every sales team ran the same math and arrived at the same conclusion, which is how every channel got flooded at roughly the same time.

Economists have a name for this. “The Tragedy of the Commons”. A shared pasture feeds a village as long as everyone grazes a few animals. Then one farmer realizes he can graze ten, and his math is correct, individually. So the next farmer runs the same math, and the next, and within a few seasons the pasture is dirt. Nobody did anything irrational. The ruin was assembled entirely out of reasonable decisions.

Cold channels were common land, every individual sender was making the smart move, and the sum of all that intelligence was destruction. We did this to ourselves. The machines just finished the job.

Cold calling worked because people answered the landline. Every call was potentially someone you knew or someone you needed, so you picked up. Then the cell phone arrived, and calls became nothing but telemarketers and bots, so we stopped answering those. Then we eventually stopped answering any and all numbers we didn’t recognize.

Americans received 3.9 billion robocalls in January 2026 alone, roughly twelve for every person in the country in a single month. What began as a flood ended as a siege.

The phone itself has turned against the caller. AI call screening is built into the default dialer on the iPhone, the Google Pixel, and the newest Samsung Galaxy. The phone answers on your behalf, asks who’s calling and why, transcribes the answer, and shows it to the owner before they decide whether to pick up. An unknown number no longer reaches a human. It reaches a machine that interrogates it first.

The executive at his desk before the admin arrived doesn’t exist anymore. The admin is software now, it never goes home, and it screens everything.

Email was once a direct line to a decision-maker. You could reach almost anyone if you knew their address, and for a while that felt like a superpower. Then the inbox filled with mass outreach, and we stopped opening everything, and we learned to scan for the names we recognized and delete the rest unread.

At least that filtering was still ours to do.

Gmail entered what Google calls its Gemini era at the start of 2026, and the platform took the job over. The inbox stopped being a passive container. It now summarizes, prioritizes, and buries messages before a human sees them, surfacing what it judges valuable and sinking what it doesn’t. Promotional language, manufactured urgency, and templated phrasing reduce your visibility even when you never trip a spam filter.

The old test was getting past the filter. The test that replaced it is convincing a machine your message deserves attention at all, and the machine rules on that before the person you wrote to has any say.

I’ve been on LinkedIn since 2004, the year after it launched. I watched the whole life of the channel from the inside. It began as a place for professional conversation, and for years it mostly was one.

Then every connection request became a sales pitch in disguise, and buyers learned to ignore strangers entirely. Many professionals now receive dozens of automated messages a week, all opening with some version of “I noticed your impressive profile,” all going straight to the mental trash.

LinkedIn has spent 2026 fighting back with detection systems that changed the rules on the volume players. Connection limits tightened, and the detection stopped counting how many requests you sent and started evaluating what happened to them. Send eighty messages and get ignored by seventy, and the platform reads that as spam behavior no matter how careful your automation was.

The algorithm now explicitly rewards authority and penalizes reach for its own sake. Every recipient who marks a cold InMail as spam teaches the machine to bury the next one a little deeper.

Three channels, one story. A channel works when it’s uncluttered. Then people pile in to exploit it. The volume degrades the experience for everyone. The users tune it out. Then the platforms build machines to do the tuning-out automatically, and the pasture is dirt.

A founder I mentor has been trying to make cold outbound work for nearly a decade. He’s an exceptionally talented operator, the type of person who can be handed the most complicated technical problem in his field and solve it. He spent bags of cash on salespeople, and when they failed, he ran every tool in the modern arsenal: the automated sending platforms, the data enrichment services, the warmed-up inboxes, the multi-variant campaigns with ten-step follow-up sequences. This spring he set up an AI agent platform and hired 140 artificial employees, a phantom company with its own CMO running outbound. It sat frozen for five days because it needed him to unlock access to a database, and he was too busy to notice.

On a call this year, I asked him one question: Before all of this, when the business was at its best, where did the clients come from?

Everything was referrals, he said. Both of his anchor clients had been referrals. The growth after that was upsells, renewals, and expansion inside relationships that already existed. His entire revenue history, the whole actual record of money entering his business, was warm. He’d spent ten years and roughly half a million dollars trying to industrialize the one channel that had never once paid him, while the channel that built his company sat in his contact list, unworked.

He isn’t foolish in the slightest he just did what the entire industry told him to do. The playbooks, the gurus, the tools, the case studies all pointed the same direction, toward scale, toward automation, and toward more. Every decision he made was individually rational, which is exactly how the pasture dies. Nobody was selling him the boring truth that his next client was probably someone who already knew his name.

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Sit with the image of those 140 agents for a moment, because it’s where the whole volume game goes to die. His machines drafting cold emails on one side. Gmail’s machines summarizing and screening them on the other. Software talking to software while two humans stand outside the loop, holding a séance and calling it a pipeline.

I should be honest about my own hands here. I use automation tools too. I keep one running for audience research and to study how my ICP behaves. The tools aren’t the sin. What I won’t let them do is speak for me, because I’ve tested what that sounds like from the other end. When an automated message lands in my inbox, I usually reply, just to see what’s behind the curtain. I write back something simple, and the response makes it instantly obvious that the sender has no idea who I am. There’s no next step and no thread to pull. Sadly, there was never a person there, just a machine spraying and a founder hoping. Buyers of all types recognize that absence in seconds, and the feeling kills the deal before it starts.

Which points at the strange gift hiding inside all this wreckage. In a market flooded with automated volume, the opposite of volume gets the attention. When every inbox is full of machine-written sameness, a single message that could only have been written by a person, for one person, reads like a hand-delivered letter. The economics inverted. Effort was once the baseline cost of outreach and scale was the impossible luxury. Scale is now trivial and effort is rare, and markets always pay for what’s rare.

The highest-return move in sales right now is also the least glamorous. Sell to the people you already know:

• Past clients.

• Dormant leads.

• The prospect who took a call two years ago and wasn’t ready.

• The person who referred someone once.

I have a few hundred people in my CRM who have at some point booked a call with me, and I rarely have to cold anything. I reach out and say some version of “since we last spoke, here’s what I’ve been finding out, thought of you.” The connection already did the hard part. The trust already exists. The machines that screen the cold channels have no jurisdiction over a relationship that’s already real.

That’s what the creative with the shot glass understood decades before any of this. He didn’t try to reach everyone. He picked one person, made one joke that person would get, spent real money landing it, and signed his name to it. Thirty years later, I remember his name, the object, and the line, which is more than I can say for any of the ten thousand identical messages that have landed in my inbox since.

The future of sales looks a lot like its past.

Fewer people, more thought, and aimed at someone in particular, by someone willing to sign their name to it.