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from fax machines to AI: what 20+ years in B2B sales has taught me about getting (and closing) leads

Bysimon@williamsfreelance.co.uk

I was reminiscing the other day about my first proper b2b sales job in advertising sales, circa 1999 and i remembered something wild…

We used to get our orders by fax machine.

Now, i’m not that old, thank you very much, but back then, we didn’t have a computer for every salesperson. CRMs? Pipeline tools? Automation? Forget it. We were armed with a desk phone, a pen, a notebook and a target to hit.

And yet… we made it work as many others did!

In fact, we sold, we closed and we hustled. Because while the tech has changed drastically, the process really hasn’t, and that’s what i want to dig into here. What 20+ years of doing this stuff has taught me about finding leads, getting them over the line, and staying sane in the process.

back then: index cards, a magazine, and a bit of cheek

My “lead list” was usually a pile of trade magazines, exhibitor lists, or a spreadsheet someone forgot to lock. If i saw a company advertising in xyz monthly, I tore out the adverts and they went on the list. That was my version of intent data!

From there, it was down to craft and tenacity:

I’d call up the company and ask the receptionist, “i wonder if you could tell me who’s responsible for placing the advert in xyz magazine?”

I’d sound like i was from the magazine. Of course, I wasn’t – but it got me the name. A couple of days later I’d call back and use their name like we were old mates.

Then, if I had no luck getting through to them, I’d follow up. again. and again. and again – and at no point would I ever leave a message!

I didn’t have automation – but i had persistence.
I didn’t have tracking – but i had a notebook.
I didn’t have templates – but i had scripts i’d learned by heart.

It was all about process: Build a list, enrich it, engage, follow up, close… and if i couldn’t close, cycle them back in and try again later.

now: ai, automations… and the same damn game

Fast forward to today and I’ve got tools that do things my 1999 self wouldn’t believe:

  • I can scrape LinkedIn bios, website copy, and public databases in seconds
  • I can personalise outreach at scale using AI prompts I’ve trained myself
  • I can segment, test, tweak, and track everything
  • I can run multi-channel touchpoint campaigns without lifting a finger (after the setup of course)

But at the heart of it?

It’s still just about saying the right thing, to the right person, at the right time and not giving up after one message.

That’s what people miss, they chase shiny tools, throw spaghetti at the wall and then wonder why no one replies.

Let me say this clearly:

the email preview is the new gatekeeper.

It’s still the same principle though, you have to find unique ways to cut through the noise and get in front of the decision maker and you’ve got seconds to make it feel relevant, warm, and worth engaging with.

what’s stayed the same (and what hasn’t)

Here’s what 20+ years in b2b sales has taught me about what really matters:

what’s changed:

  • the tech
  • the channels
  • the tools
  • the way people buy
  • the noise level
  • the job titles

what hasn’t:

  • you still need to build a list
  • you still need to follow up
  • you still need to personalise
  • you still need to understand why they’d buy from you
  • you still need to be consistent and persistent
  • you still need to talk to humans, not job functions

Cold calling is a valid route, so is email, so is social.

What matters is that you’re not relying on one touch, or one post, or one ad.

It’s the orchestration that works – not the tool.

from “hello” to “let’s go”! my sales process, then vs now

then:

  • built lists from trade mags and exhibitor directories
  • used cheeky lines to get past the gatekeeper
  • followed up with a notebook, phone, and fax machine
  • relied on instinct and repetition
  • worked hard and hoped it stuck

now:

  • build smart, segmented lists using enriched data
  • personalise at scale using ai and human logic
  • test messaging across email, linkedin, and beyond
  • use insight + instinct to tweak, track, and improve
  • work smart and only work hard where it counts

I will still occasionally pick up the phone, but usually for warm leads and I’ll say it – cold calling still works.

I’ve just chosen a different stack that suits how I work (and live) right now and that’s the joy of modern sales – it’s as customisable as you want to make it!

what i miss… and what i’m grateful for

There was something gritty and satisfying about building a list from scratch, about crafting lines to get past the gatekeeper and about being clever and resourceful with no digital tools in sight.

I miss the simplicity, the spreadsheets full of direct dials that were absolute gold dust and I miss turning up at trade shows with a list, a pitch, and a pen (which I could still do I suppose)!

But I don’t miss being chained to a desk with no flexibility and I know I’d miss time with my family. Really importantly, I don’t miss the guesswork, being able to work on accessible data to make driven decisions.

Today, i get to write blog posts like this!

I get to build an online presence that works while I sleep.

I get to test messaging, segment lists, automate follow-up and still pick up the phone when it makes sense.

I get to work smart, not just hard and be there for the moments that matter most at home.

in summary…

  • tech changes.
  • tactics evolve.
  • channels shift.
  • but great sales? great sales is timeless.

It’s about building a system that works for you, showing up consistently, and always putting the right message in front of the right person, whether i’m doing it with a fax machine or a GPT prompt – that’s the bit that’s never changed.

want more like this?

I share real-world lessons on sales, lead gen, and growing your business the smart way – no fluff, no fake gurus, just the good stuff.

Drop me a message (simon@williamsfreelance.co.uk) or follow along on LinkedIn if you’re into that kind of thing.