I won a $20m deal with one of the largest banks in the world. The biggest of my career.
Looking back, I can see the exact moments it was won — the moves that mattered, and the mistakes I was lucky to survive.
I want to walk you through all of them.
Everything I teach in my training comes from deals like this one. So here's the whole story, scar tissue and all. Hopefully you'll recognise a few of your own deals in it.
The Start
Like many deals, it started with a one-hour presentation to a mid-level employee. Their requirement was embryonic, and I did what salespeople do a few times a week. Had a conversation, put up a few slides, told a story.
Then, as often happens, it went quiet for several weeks.
Of course I followed up. But big decisions need the whole business to move, and there's almost always a gap between the meeting and the movement.
Almost Falling at the First Hurdle
After a couple of informal meetings, the RFI document landed, and the match was obvious. Our language was peppered all through it. Not enough to say it was written for us, but our story had clearly landed.
It felt real. The chase was on.
I wasn't experienced at running RFx exercises. I'd done a couple at my previous company, mostly carried by a bid team. This was the first time I was leading the response myself.
At that previous company, RFx's were uninspiring tick-box exercises, so I'd never built any craft of my own. Bid teams can help, but in some organisations I think they stop Account Execs developing a critical skill: the strategic orchestration of a response.
So I shot the mandatory response spreadsheet off to a couple of internal teams and asked them to fill it in by a date. This is how most salespeople "manage" an RFP. It's also the root of all mediocrity in the response.
As the deadline approached, the internal contributors fobbed me off. They were busy, they were behind, but they promised they'd have it to me on time.
One delay led to another. And then suddenly there I was, the day before submission, missing around half the information I needed.
I knew I'd lost control. I went to my boss, the fiery founder and CEO of this fast-growing scale-up. He took the reins, summoned a large group into a boardroom, delivered a bollocking, and set everyone to work.
The next few hours were a flurry of stressed, intense work from everyone. And we produced a document in a single day that was better than any I'd seen in my career. A clear sign of a bar in this business I'd been blind to. (I was six weeks in at this point.)
After I'd submitted, the CEO summoned me into his office, a big desk in the open-plan floor. "What the f*ck was that about, James?!"
I spluttered that I'd made repeated requests, been ignored, and been let down.
"No James, it's YOUR fault!! — Your Account, Your RFP, Your Responsibility!"
I felt myself blush crimson. But more than the humiliation, something cut deeper.
He was right, and I knew it.
It was a cold bucket of water over my head. In that single moment I learned one of the most important lessons that eludes many people their whole career: true accountability has nowhere to hide and no one to blame. I was accountable for the quality of that document and for managing the internal team. I'd let it get away from me. It was all on me.
He was (and is) an uncompromising and brilliant man, and I'm lucky I left that conversation with my job. I wouldn't make that mistake again.
What I took from it was an intensity and clarity in managing others. It's a skill every salesperson has to learn as they move into true big-ticket sales, and many fail because they can't lift themselves to the level of an orchestrator. Be clear on what you need from people. Be even clearer in telling them.
Lesson 01 — Accountability Has Nowhere to Hide
Your account, your RFP, your responsibility. The moment you're blaming the internal team for a weak response, you've already lost. Owning the whole outcome, including the parts other people touched, is the line between a rep and an orchestrator.
Back in the deal, we made it through to the next stage.
My First Killer Move: The Weaponised PoC
A series of onsite meetings followed the RFI, and we steered them into a Proof of Concept. Our technical team delivered an excellent one. A real body of evidence for our solution.
PoCs are often misunderstood and under-used. They carry a credibility no amount of slideware can match, because they're run against real-world prospect scenarios.
(I often run training on using PoCs as a weapon. There's far more to it than I can fit here. For now, just know it's a tool you need to master.)
Once the exercise was done and our performance captured in the buyer's spreadsheet, I didn't let the code be deleted. I turned it into a fully customer-branded showcase and toured it around the other offices and divisions of this global business, showing them what we'd built.
It was so powerful because it ran on their systems, integrated with their tools, using their data. Far more convincing than any normal demo. I quickly opened a series of parallel opportunities across different global markets and divisions in the group, including a very promising one with the global SME banking line.
Lesson 02 — Never Let a Winning PoC Die in a Folder
A proof of concept running on the customer's own systems, data and tools beats any demo you'll ever give. So when it lands, don't delete it. Brand it, keep it, and walk it round the building. Mine opened every other door in the account.
Some salespeople will warn you off opening parallel opportunities: more stakeholders, more voices, more risk. I think that's backwards. Multi-threading, both the stakeholders inside one deal and parallel deals across a group, is exactly how you hunt big game. Yes, more threads means more variables. But the spread is what protects you.
This multi-threading would go on to save the entire deal from certain doom. More on that later.
Lesson 03 — Multi-Thread Everything: Stakeholders and Opportunities
One thread is a single point of failure. The more senior relationships and parallel deals you run inside an account, the harder it is for any one person leaving, or any one "no", to kill you. The real risk isn't spreading too wide. It's hanging your whole year on a single champion.
Now I had several interesting parallel conversations. One of them started to show real promise.
The Second Opportunity Begins to Open
Some weeks after the showcase, I spoke with a Project and Change Manager at one of the new divisions I'd toured. He had a requirement our solution fit perfectly: an impending end-of-life transformation for a major platform we could replace.
The business was on course to build the replacement internally. But after seeing our showcase, he thought our technology might be the better option. Trouble was, plenty of senior stakeholders were dead-set on building in-house. They believed no external provider could shortcut the complex integration with their legacy back-end.
Converting senior detractors needs something compelling enough to make them change course. So I proposed a paid two-week technical PoC, in which we'd connect to and surface data from their monolithic back-end into our platform, proving an objective speed-to-market advantage.
At that point it would be fact, not opinion.
PoCs aren't about proving your solution is worth buying. They're about proving it can actually be deployed, and so deliver the outcomes you've been promising.
My logic for making it paid was simple. Getting the prospect to pay, even a nominal £10k, would test his influence and force him to get the exercise approved, which raised its visibility with senior management.
Charging for a PoC isn't about revenue. It's about skin in the game. PoCs are rarely the shortest route from here to a sale. They take time. But the credibility they buy is second to none. They lay the foundation you need when you're building big deals.
The results presentation left the executives' jaws on the floor. Any scepticism in that group was swept away. From that moment the second opportunity was as hot as the first. And several times larger.
Lesson 04 — Make Them Pay for the PoC, Even a Token Amount
A nominal fee (mine was £10k) isn't about the money. It forces your champion to get budget approved, which tests their real influence and drags the PoC in front of senior management. Skin in the game changes how seriously everyone treats it. A free PoC is the easiest thing in the world to ignore.
Suddenly the deal was the largest opportunity in our company's history. I was spending a lot of time with the CEO. After my early faux-pas, he was starting to see I was making interesting moves, and getting traction in an account far bigger than anything they'd cracked before.
With this new opportunity we'd have to jump through all the usual hoops. Over the next six months we ran workshops aplenty, multi-threaded, and went through a full RFP. I'll spare you the details of those sessions. They were unremarkable and not pivotal. But they happened, and that matters: big deals turn on a handful of key moments, but they still have to clear the routine process hygiene of any other deal.
A Friendly Face
Some of what decides a deal happens long before the deal even starts.
In this case, one of the key sponsors of the second opportunity had been a stakeholder on a deal my company lost two years earlier, before I joined. They couldn't buy back then, it was simply too expensive, but they walked away with a strong, positive memory of the platform and a real sense of FOMO.
Did that old loss win me this deal? On its own, no. But a buyer who'd wanted us for two years, and now had the budget he didn't have back then? That didn't hurt.
The point: your industry is smaller than you think, and memories are long. The deal you lose this year can win you a bigger one later, as long as the people you lost to remember you well.
Lesson 05 — Every Interaction Is a Deposit, Even the Losses
Your industry is smaller than you think, and people move around. A buyer who liked you on a deal you lost can pull you into a far bigger one years later. So lose well. Leave people wanting you. The reputation you build today is pipeline you haven't met yet.
The First Opportunity Wobbles
By this point I had two significant opportunities running. Both knew about each other and compared notes, but they ran through two separate reporting lines, two P&Ls, and were otherwise independent.
I was having a coffee with my champion on the first opportunity when he dropped a reference to what they were trying to build that I didn't fully understand. A piece of industry jargon I wasn't familiar with. Blink and you'd miss it. But my gut told me it was significant. That it was crucial to what they wanted to build, the outcome they were after. And I didn't understand it.
I noted the word down, went away, did my own research, and educated myself. I reached out to bankers in my network and called in favours, getting more expert in this one area. I knew I needed to be able to talk about this business outcome intelligently.
My hunch was right. It wasn't just important. It was critical.
Me finally understanding their ambition wasn't some brilliant move. It was me correcting a massive mistake that should never have happened. Like a lot of vendors, we'd been inwardly focussed on our tech and our capabilities, and nowhere near curious enough about the prospect's vision for what they wanted to build, and why.
"Can you do this? Yes, here's how…" That sums up much of our engagement up to that point. And I suspect, if you're honest, you'd admit you've been that way on some of your own opportunities — past or present?
My realisation came not a moment too soon. There had been quiet rumblings at the prospect that we "didn't fully get it". They were right.
It was a mistake we shouldn't have made in the first place. But it was my team's decisiveness in understanding and responding to the use case that saved us. We spent three weeks preparing a full design for their vision, showing how deeply we got it. The CEO and I flew out to meet the divisional CTO and his second-in-command and present our vision for their company.
The meeting was an outstanding success. We left with a wink and a nod from the top decision-makers.
Lesson 06 — Get Obsessed With Their Outcome, Not Your Tech
"Can you do this?" "Yes, here's how." That reflex feels like good selling. It isn't. We nearly lost a deal because we knew our own product inside out and their actual ambition barely at all. The vendors who win stay curious about what the customer is trying to build, and why, long before they get to how.
Lesson 07 — Grab Your Most Senior Person and Get on a Plane
When it mattered, my CEO and I flew out to present in person. The effort itself is the message. It tells the buyer how much they matter to you. Most big decisions aren't logical, they're emotional, and you can't send that signal in an email.
In the weeks that followed we went through final due diligence, contract negotiation, and sent the contract for signature. The first opportunity was at the finish line. The second was progressing nicely.
The end seemed close.
Disaster Strikes
For salespeople, the moment you lose a big deal gets burned into your psyche. They're "where were you when Kennedy was shot" moments.
I was on holiday with my family at Centre Parcs. The contract had gone for signature, and I had a bottle of champagne in the fridge waiting to be popped.
I called my champion.
"Is it done and signed?" I asked.
"Er, probably not. The regional CTO got fired."
"H- H- How? W- When?" I stammered.
"This morning," he said. "We're going to need to put things on ice until we find a replacement."
My heart sank. I'd been so close. Now I had to call my boss, the CEO, and tell him a $3m deal had slipped out of my forecast on the very day it was meant to be signed. Not a call any salesperson wants to make.
Over the next few weeks my luck went from bad to worse. The new regional CTO came in, favoured our competitor, secretly engaged them, and ghosted me.
The deal was slipping away. A year of my life, gone. It felt surreal to have got so close.
Then something just as unexpected happened. The new regional CTO had been overruled by the Group CTO (someone I'd never managed to reach, despite trying) and ordered to stand down and wait.
It turned out our profile as a vendor had been climbing through the global ranks, off the back of my earlier roadshow and parallel opportunities. The decision was now a global concern. The Group CTO of this mega-bank had decided that, strategically, it made more sense for us to be selected as a group standard, and pulled the whole thing under his own team's control.
Remember the roadshow? The parallel opportunities I'd opened across the group? That's what saved me here.
What had started as a single $3m deal was now a group-wide standard. At roughly $20m, it represented about 20% of my whole company's revenue for the year. The pressure on me was insane. But it felt like we'd reached the top of the tree, and things were looking good.
Perfect timing for something to go wrong.
A Final Stick in the Spokes
The final stage of group-level due diligence was handed to the Group CTO's personal lieutenant. A brilliant but brash man, clearly the architect-equivalent of the Group CTO's attack dog.
We'd present to him and his team and be met with things like "that's a f*cking stupid thing to do, because of X, Y and Z."
You had to really know your shit and have the confidence to challenge him, or he'd go over you like a steamroller. Fortunately I was backed by a team that could calmly stand up to those highly emotional outbursts.
During one meeting he quietly pulled me outside. "You know I've been tasked by the Group Board to make a decision?"
"Er, yeah," I said, sheepishly.
"Well. I want you to give us your source code as part of this deal, or I'm going to kill it. Dead. Understand?"
He didn't want a response. Which was good, because I had no idea how to reply.
It was like me storming into a KFC, dangling an order for three million chicken buckets on the condition they hand over the Colonel's secret recipe. It was something I couldn't say yes to, and had no idea how to refuse.
I talked to my CEO to make sure he knew about the demand, but I already knew what our answer had to be. No software vendor can ever give up its source code.
I knew I needed to say "no" in a way that exposed how unreasonable the request was. So I scheduled a call with the exec who'd made the demand.
"I'm sure the reason you want the source code is just in case something goes wrong and you're not dependent on us, right?"
"Er, yeah, that's it." What else was he going to say? That he planned to reverse-engineer our product? Of course not.
"That's reasonable," I said. "So how about this: we make provisions in the contract that if we have multiple P1 breaches in our service, we release the code from escrow. That protects our IP, but it also gives you the code to take control if we fail on our service and resilience obligations. That'd be fair, right?"
I'd left him nowhere to move. He could either accept my very reasonable solution, or admit his intentions for our source code weren't honourable.
The final obstacle fell.
Lesson 08 — When a Demand Is Unreasonable, Expose the Fear Behind It
He wanted our source code. The answer was never going to be yes. But a flat "no" would have killed the deal. So I didn't argue the demand. I named the fear underneath it ("you just want cover if we fail, right?") and solved that instead, with an escrow that only triggered if we breached. He either took the fair version or admitted his real intent. Don't fight the position. Find the fear and serve it.
The Final Call With the CTO
My CEO and I were invited (by which I mean summoned) to a call with their Group CTO. A comparatively softly spoken, easy-going chap. A lot of large businesses have very likeable senior execs surrounded by brutal lieutenants. The steel hand in the velvet glove.
The final, and very reasonable, objection was this: "You need to understand that the price we're talking about here (eight figures) is at the very limit of what we'll spend on any software, globally. A dollar more and it simply stops making sense for us to license it. We'd either need to buy your company, or build it ourselves."
It's a fair point, and one vendors often miss. Past a certain scale of users, the incremental cost of each new user has to fall to near-zero, or it stops making sense for anyone to buy a technology off the shelf. Licence costs can't grow in a straight line forever. They just can't.
The final concession we made was a cap on the future growth of the account: an option for one final payment, after which the licence became essentially unlimited. What's often called an Enterprise Licence Agreement. The ultimate all-you-can-eat buffet.
The terms were agreed. The deal was almost done.
Lesson 09 — At the Top End, Your Pricing Model Has to Bend
Past a certain scale, the buyer's maths gets brutal: if every extra user costs them more, at some point it's cheaper to build it themselves or buy your company outright. Licence costs can't climb in a straight line forever. Know where that ceiling sits. An enterprise licence or usage cap is often the thing that gets the very biggest deals over the line.
Dragging It Across the Line
Even with board approval, I spent four months locked in back-and-forth with their team and our lawyers, arguing over liability caps, IP ownership and indemnification. (If you know, you know.)
I came out of it knowing about as much commercial law as most graduate lawyers.
Enterprise salespeople have to bring two sets of procurement teams and lawyers to agreement. No easy thing, since lawyers exist to drive their own party's risk to zero, and they don't compromise easily. This is where a skilled Enterprise Account Exec earns their keep: by being the arbiter of reasonable outcomes.
The Psychological Aftermath
At the top of Everest, climbers often describe the moment as an anti-climax. They're utterly exhausted, running on fumes, with no energy left to enjoy the view.
That's exactly how I felt. I wanted to feel elated. I didn't. I was spent.
Exhausted.
Relieved.
Frankly, still in disbelief at what we'd actually pulled off.
But not happy. As odd as that sounds.
In the four months that followed I had a series of panic attacks. It's really hard to explain what a panic attack feels like to anyone who hasn't had one. It feels like you're drowning in fresh air. It turned out the pressure of this deal had been crushing me and holding me up at the same time.
There's no making a deal like this low-stress, so let's not kid ourselves. What we can do is learn our craft well enough to make clear, confident choices. Some of the moves I made were inspired strategy. Plenty of others were me reacting in the moment to an error I shouldn't have made, and needed to correct.
And if you're a sales leader reading this: appreciate the pressure your salesperson is under. Make sure you're a force that helps. Not just a pressure-multiplier.