Uber Is Not Your Past. It Is Your Pitch.

I was on a coaching call recently with a guy who had one of the most legitimately impressive career backgrounds I've come across in a while. Former senior PM at Uber - and not just any Uber role. He was there during the Travis Kalanick hypergrowth years, doing 0-to-1 work on a new marketplace product. He scaled it to significant revenue. He was in the room, at the company, at the exact moment that company rewrote how cities move.

And he had filed that entire experience under: probably not relevant anymore.

He came to the call wanting to talk about LinkedIn messaging tactics. He was getting a 5% reply rate, hadn't cracked positioning yet, and was blasting AI-consulting pitches at Fortune 500 companies that read like a McKinsey deck written in a hurry. But before we got to any of that, I asked him one question: what's the most impressive thing you've actually done in your career?

He mentioned Uber almost apologetically. Like he wasn't sure it still counted. Like the era was too old, too web 2.0, too far removed from the AI narrative he was trying to build.

I stopped him right there.

The Cognitive Error That Kills Consulting Pitches

When people pivot into a new space - whether that's AI, consulting, a new niche, whatever - they almost always make the same mistake. They think the pivot requires a clean break. New positioning, new language, new proof points. And in trying to sound current, they throw out the one thing that makes them believable: the thing they actually did that nobody else in the room did.

This guy had spent years trying to position himself as an AI product leader. His LinkedIn headline was something like AI product leader who takes AI opportunities to post revenue. Technically descriptive. Completely forgettable. Not because it was badly written - but because he could have been anyone. Every second person on LinkedIn right now calls themselves an AI anything. There's no shortage of AI consultants. There is a shortage of people who can say they built a product at Uber from zero to real revenue during the era that turned the company into a verb.

The mistake he made is one I see constantly: treating novelty as a credential and treating experience as a liability. It's exactly backwards. In consulting and B2B services, novelty is actually a liability. Familiarity is the currency. When a head of strategy at a 10,000-person company is evaluating whether to hire an outside expert, they're not excited about AI in the abstract. They're scared. They're scared they're going to go all-in on something, blow up something important, and have to publicly reverse course. They've watched what happened to Klarna.

The Klarna Frame Is the Fear Your Client Won't Say Out Loud

If you've been paying attention to enterprise AI adoption, you already know the Klarna story. The company famously went all-in on AI for customer service, laid off hundreds of people, and then had to reverse course after customer satisfaction dropped and quality degraded. The CEO eventually admitted that cost had been "a too predominant evaluation factor" - which is a polished way of saying they broke something that mattered in pursuit of efficiency metrics. The story became a cautionary tale that's now cited in boardrooms.

Here's what's interesting about that story from a sales perspective: it crystallizes the exact fear that is sitting in the gut of every VP of Product, every Chief Digital Officer, and every operations lead at a large company right now. They've heard the AI pitch a thousand times. They know they need to do something. But they also know that doing the wrong thing - or doing the right thing wrong - could be a Klarna-level embarrassment. They've given presentations on the Klarna story. They've used it in internal decks as the example of what not to do.

So when this guy on my call asks me which angle to lead with for his AI consulting pitch, and one of the options is "get the most out of AI without destroying your business in the process" - that's not just a clever headline. That is the exact sentence that is already playing on a loop in the head of the person he's emailing. You're not creating fear. You're naming the fear that already exists and positioning yourself as the person who prevents it.

But here's the thing he didn't see at first: the reason anyone would believe him on that promise is Uber.

Why the Old Story Is the New Pitch

At Uber during the hypergrowth era, new tools, new processes, and new technology were arriving constantly. The company was implementing things at a speed that had no precedent. And someone in that environment - someone whose job was to take a new marketplace product from zero to real revenue - got extraordinarily good at a very specific skill: figuring out what to implement, how to implement it, and what would destroy the business if implemented wrong.

That is exactly the skill the market needs right now, applied to AI.

The through-line isn't that he used to work at Uber and now works in AI. The through-line is that he developed a specific judgment - a pattern recognition for technology adoption that works versus technology adoption that blows up - and that judgment is now more valuable than it has ever been, because every large company is being asked to adopt something new, fast, with enormous downside risk if they get it wrong.

When I laid that out on the call, his response was basically: oh.

That's the response you want when you've found your real positioning. Not excitement, not "that sounds good" - but genuine recognition, like something just clicked that should have been obvious.

The One Funnel Strategy

Once we had that frame, everything else became simple. He needed a landing page - not a 10-page website, just a single page - that stated the offer, included the fear-based headline, and showed the logos of the major companies he'd worked with. That's it. No jargon. No academic speak about AI adoption frameworks or data flywheels. Just: here is the problem, here is who I am, here is what we do.

I call this the one funnel strategy. The idea is that anywhere someone finds you online - LinkedIn, a Google search, a referral who looks you up - they should see the same thing, and that thing should be completely clear. Not aspirational. Not broad. Specific enough that when the right person reads it, they think: that's exactly what I need.

Most people I coach have fractured funnels. Their LinkedIn says one thing, their website says another, their outreach emails say a third thing. They've been around long enough to have done a lot of different things, and all of those things are visible, and none of them add up to a clear, singular offer. The result is that prospects read their profile and come away with no idea what to do next - even if they're the ideal buyer.

Fixing this is not a design problem. It's a clarity problem. And you don't fix a clarity problem by hiring a copywriter. You fix it by doing the hard work of picking one thing, getting the language right, and then having the discipline to say that one thing everywhere until it sticks.

His draft headline became something like: Get the most out of AI without destroying your business in the process. Former [Big Tech] Senior PM who scaled products from zero to eight figures during the era that rewrote how companies scale.

Is that the final version? Probably not. But it's ten times more readable, more credible, and more specific than what he had before. And more importantly, it leads with the fear the buyer already has and positions the credential as the reason to believe the promise can be kept.

Warm Network First. Cold Outreach Second.

After the positioning work, I told him something that most people in the cold email world don't want to hear: don't go cold yet.

Not because cold outreach doesn't work - it absolutely does, and once your positioning is locked, cold email is one of the most scalable ways to grow a B2B consulting business. But cold email only works when the offer is sharp enough that strangers respond to it. If your positioning is still rough, you're going to get nothing from cold outreach except silence - which is exactly what he was getting. Ten messages, zero responses.

Before you go cold, you need to run your positioning past people who will actually talk to you: your warm network. Alumni, former colleagues, LinkedIn connections you already have some relationship with. In his case, that meant people he'd worked with during the Uber years who had since moved into VP and director-level roles at other companies. Some of them were sitting in exactly the positions he wanted to target.

The reason you do warm network first isn't just to get meetings. It's to get feedback. When you're standing in front of someone who knows you, or on a Zoom call with someone who went to the same company or school, they'll tell you the truth about whether your pitch lands. They'll tell you if the headline is confusing, if the offer makes sense, if the fear you're naming is the actual fear they have. You can't get that feedback from silence.

Use those conversations to pressure-test your copy. Then take what you learn and rewrite the positioning statement. Then - and only then - go cold. At that point, you're not guessing. You have real signal about what's working and why, and you can scale it.

If you want a head start on the outreach structure once you get there, the Top 5 Cold Email Scripts I've put together are a solid place to start - especially for B2B consulting offers where you need to establish credibility fast. And when you're ready to build your list of target companies and decision-makers, tools like ScraperCity's B2B database can help you pull the right contacts at the right companies - pair that with a sender like Smartlead or Instantly and you've got a real outbound system once your positioning earns it.

The Question You Need to Answer Before You Send Another Message

Here's the thing about this guy's situation - and about most of the people I coach who are struggling with positioning: the answer was always there. It wasn't buried. It was literally the first impressive thing he told me when I asked what he'd actually done. He just didn't trust it.

There's a specific type of self-doubt that happens during a career pivot. You've been doing something for a long time, and now you're doing something new, and the old thing feels like a different chapter - maybe even an embarrassing one if the company or era has become associated with a style of doing business that's out of fashion. Uber during the Travis Kalanick years has some baggage. Move fast, break things, grow at any cost. He was probably half-expecting me to wince when he mentioned it.

I didn't. Because none of that is what a prospective client hears. What they hear is: this person built something from nothing at one of the most operationally complex companies on the planet during a period of unprecedented growth. That's the signal. The rest is noise.

Whatever version of this story you have in your past - the thing you did that you've been quietly filing under "old news" or "doesn't fit my current brand" - it might be the most important thing you own. Not as nostalgia. As proof.

So before you write another cold email, update your LinkedIn banner, or redesign your website: ask yourself one question. What is the one thing in your career history that would make a stranger lean forward? Are you leading with it - or hiding it?

If you want help figuring out how to structure and position an offer like this, check out the 7-Figure Agency Blueprint - it walks through the offer-market fit work that has to happen before any outreach can scale. And if you want live feedback on your positioning, offer, and outreach in real time, Galadon Gold is where that work happens.

The credential you're burying is probably the only reason a stranger would trust you enough to buy. Stop hiding it.