Lots of people talk about sales, but don’t have the lived experience.

And it’s only through skinning your knees, lots of mistakes and losses that you're able to find the strategies that win.

After 23 years in the agency world, founding, scaling and two exits. With one of those acquisitions by Accenture. You’ve most certainly made enough of those mistakes and learned the hard-won lessons I wish someone had told me earlier.

The bottom line? Sales is difficult. But that's hardly news.

Anyone who tells you otherwise is either lying or hasn’t done it long enough.

Over two decades of running businesses, being revenue responsible and owning pipelines, I’ve learned that winning work is rarely about having the best pitch deck or the slickest credentials.

It’s about something far less glamorous.

It’s persistence, effort, and genuinely giving a shit.

So let's look at five client wins that shaped how we think about sales. Not because they were easy, but precisely because they weren’t.

The ‘Five-Year Nurture’

We won a major retail banking client. A big name on the high street, a great brand and a chance to do some brilliant work. But it wasn’t a straightforward process.

It took five years to find a way to get the first deal over the line.

Five years of relationship building. Five years of staying visible. And across those five years, we survived three marketing director changes. Each time leadership shifted, we were back to square one. The trust we’d built? Gone. The momentum we’d created? Evaporated. Proper Snakes and Ladders stakes.

Most people would have walked away. But we stayed.

And I’m glad we did because the persistence paid off. We closed a gateway offer to get the relationship going. A £20,000 strategic project to show what we were capable of.

From there, the account grew to £1 million annually, with work spanning their public website, mortgage experience redesign, and mobile applications and much more.

Why? Because the bank was the right fit. Not just commercially, but culturally. We made a deliberate choice to be patient with this opportunity, even when forecasts had to be adjusted, and internal pressure grew.

We turned up, we added value, and showed interest in their business. We were consistent and determined. We also mirrored the values and brand characteristics in the way that engaged, even in the softer aspect of our tone of voice and style.

The lesson?

Not all deals move quickly. Not all deals are easy.

So be patient, but be selective. You can’t run this playbook on every opportunity. The economics don’t work.

Choose your long-game targets deliberately, define clear parameters for your investment of time and effort, and then stay the course.

The lucky comment

Sometimes opportunity arrives when you least expect it.

With this major UK based aiurline, we found a post from their Marketing Director asking if anyone could recommend a mobile application partner.

It was brilliant timing. A chance encounter. But a bold response to a social media comment.

The reply?

“Yes, of course. Us.”

Their response? A meeting. Which led to a half-million-pound first phase and substantial ongoing work.

But winning that deal was genuinely difficult.

We had zero sector experience. We were up against larger competitors with aviation credentials and incumbents who’d been cultivating the relationship for years. And whilst we had transferable expertise, they wanted to see relevant experience we simply didn’t have.

Our strategy was almost embarrassingly simple. Outwork everyone.

We sent our marketing manager on two days of flights. Ten back-to-back trips around the UK. He interviewed passengers and staff, photographed screens, onboard experiences, and mapped the entire customer journey. We became their customer, quite literally going the extra mile.

When we presented that research, complete with videos, photos, and a detailed experience diary, alongside our strategic thinking and design concepts, the competition became invisible. We’d demonstrated something no credentials deck could. That we cared enough to truly understand their business.

The lesson?

Being the wild card or underdog in a process can be a huge benefit. And when you lack experience, compensate with effort.

Become your prospect’s customer. Experience their product. Show them, through action, not claims, that you’re invested in understanding their world.

The relationship that followed

My biggest deal ever was a £27 million three-year programme with a global asset management business.

We even displaced one of the global consulting powerhouses along the way, too.

Which sounds impressive in a case study, but the reality was that, to even be able to talk about those deals, it started with some very basic services years and years before.

Six years before the ‘big deal’, we began by placing individual resources for the client in a previous business.

Nothing glamorous, nothing strategic. Just a very basic supply of resources. Basic body shopping of skilled team members.

But we built trust slowly, grew the relationship carefully, and focused obsessively on making our main contact successful.

The account plateaued around £1.5 million annually. But we had made it past supplying resources and had begun delivering end to end proejcts. Some of which were height of innovation for the asset management market.

Then the client stopped returning my calls.

When he finally got back to me, I assumed we were getting fired.

“Are you in the office? Yes? Ok, I’m coming over.”

Instead, they told me they’d quit their job. But couldn’t tell me where they were going yet, but said that when they landed, we’d “do it properly.”

Six months later, after the non-compete cleared, they landed in the new business, and we won our first project. Displacing a global consulting powerhouse along the way.

What followed was a rapid succession of additional wins across that year. Followed by the ‘big’ win.

The lesson?

Quality of service and strength of relationship is the ultimate sales strategy.

We didn’t know they’d change jobs. We couldn’t have predicted the scale of the opportunity. But because we’d focused relentlessly on helping them succeed. Taking small wins, being patient, and delivering exceptional work. We’d earned something invaluable. A client who wanted to bring us with them.

The business case builder

The brief from one of the UK’s leading newspapers was exciting.

Build their Buzzfeed competitor.

We were working directly with their Managing Director, an ambitious client wanting to do genuinely innovative work.

One problem: “I’ve got absolutely no money for this. Yet”

My heart sank. This wasn’t a negotiating tactic. They genuinely didn’t have a budget allocated. But they did have access to investment. They just didn’t know how to make the case for it.

So we helped them build one.

We worked strategically alongside their team to model the business case, understand unit economics, and articulate exactly how this product would generate returns. We even helped structure launch partnerships with an equally innovative retail bank, which became one of the inaugural advertisers, validating the model and sweetening our economics.

The lesson?

Think commercially about your clients’ businesses, not just your own.

Sometimes the barrier isn’t convincing them you’re the right partner, it’s helping them unlock the budget in the first place. Be willing to invest in that strategic work. It pays back.

The progressive disclosure

When a brief for the UK’s biggest coffee company arrived through an intermediary, we were excited.

It was a chance to do something tangible in the physical-digital space.

The challenge? The intermediary didn’t know us. We had no relationship capital to draw on.

Our strategy. Progressive disclosure.

Wow them at every interaction and break the process as best we can.

Rather than saving everything for a final pitch, we engineered additional touchpoints throughout the process. Each interaction delivered something unexpected. First briefing? We showed up with initial thinking. Between meetings? We sent strategic frameworks. Next session? Conceptual designs. Then mental models. Then, high-fidelity concepts.

Sounds simple, but the progressive disclosure kept everyone on their toes. Every time they met with us, they didn’t know what they were going to get. Except that it would be good.

We were doing the “surprise and delight” thing before they’d even signed a contract.

For the final pitch, we invited them to our office. We’d built a fully functional prototype on a portrait touch screen monitor rig to mimic the coffee machine. The massive screen, the working interactive ordering flow, and the animations were really cool to see. But even better to interact with.

“Would anyone like a cup of coffee? Come and experience it.”

They pressed buttons. They watched animations. The only thing missing was actual coffee dispensing. By the time they’d finished the demo, no one else stood a chance.

The lesson?

Show, don’t tell.

Don’t promise what working with you will be like, demonstrate it. Keep prospects curious about what’s coming next. And when possible, make the competition invisible by the time decision day arrives.

Let’s wrap this up

Looking back across these wins and the many, many losses that didn't make it into this piece, a few principles emerge.

Persistence and patience pay off. But only when applied selectively to the right opportunities. Define your parameters, stay the course, and accept that some five-year pursuits won’t convert.

Effort and energy differentiate. When you can’t win on experience or credentials, win on caring more than anyone else. Become the customer. Go the literal extra mile.

Quality of service is the foundation. Relationships follow people. Deliver exceptional work, help your clients succeed, and opportunities will find you. Sometimes from directions you never anticipated.

Strategic and commercial thinking matters. Understand your clients’ businesses as well as you understand your own. Sometimes your job isn’t just to win the work. It’s to help them find the budget.

Showing beats telling. Every time. Don’t describe what you’ll do. Just do it.

None of this is revolutionary. But these are lived experiences, from the front line of sales. Winner high profile work and big-ticket deals.

The gap between knowing these principles and actually living them. Consistently, over the years, through setbacks and marketing director changes and pitches that don’t land, is where most sales efforts fall short.

The logos on your credentials slide are the end of the story. The persistence, the early-morning flights, the business cases built on spec, and the five-year relationship nurtured.

That’s the actual work of winning.

It’s not easy. It’s never easy. But it’s worth the effort.

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