No, you’re not stepping away: The 6-stage guide to founder-led sales

Every founder CEO has entertained the same fantasy – I certainly did. Hire a hotshot salesperson or VP Sales, hand over the pipeline, and get back to the “real work” of product or strategy. Maybe you’ve closed a few deals and think you’ve earned a graduation out of the sales grind. Sounds lovely, doesn’t it?

Shame that it’s absolute cobblers if you want to keep growing.

The reality is that there is no magical transition where you, the founder, get to swan off and never sell again. Time and again I see the same mistakes: the first sales hire is a costly misfire that sets you back at least six months, or you bring in a sales leader far too early, or you step away from sales entirely to focus on product.

Lots of founders screw this up. They either bail out of sales as soon as they can – and watch conversion rates plummet – or they hang on too long and become the bottleneck that chokes their own growth. The truth is crystal clear: you will be leading sales in some capacity from day one until the day you sell, leave or retire. Get used to it.

Now, this doesn’t mean you’ll be cold-calling prospects forever. The role evolves. The way you drive revenue at £0 is very different from how you do it at £10M. I’ve spent 20+ years in the sales trenches and coached hundreds of founders, and I’ve noticed a six-phase pattern in successful founder-led sales. Each phase builds on the last, and knowing where you are (and what’s coming next) is the difference between scaling smoothly and running your company into the ground.

Phase 1: Finding early product-market fit (PMF)

This is ground zero. You’ve got a half-decent product and a head full of ideas. Who’s going to sell it? You. At the start, you are the sales team – the only idiot daft enough to believe in this thing 100%. Everything’s scrappy and mildly chaotic. You’re running on caffeine and adrenaline, punting your vision to anyone who’ll sit still long enough, convinced you’re one decent meeting away from a life-changing deal. There’s no process, no playbook, just organised chaos and blind faith. And that’s exactly how it should be. Right now, your unfair advantage is simple: you care more than anyone else on the planet.

But finding product-market fit isn’t as simple as lobbing your thing at anyone with a credit card. If your idea of a target customer is “anyone with a budget”, you haven’t got a target, you’ve got a fantasy. As I’ve said before, try to be everything to everyone and you end up being nothing in particular to anyone. That’s how you end up with beige positioning, wallpaper sales pitches and growth that wheezes along at best. The best firms don’t spread themselves thin – they pick a very specific Ideal Customer Profile and a problem that really bloody hurts. So before you torch your seed money and convince yourself a bit of keyword research is job done, pick one customer archetype and one sharp, painful problem. Sell to them. Everything else is background noise.

Your goal in phase 1:
Get real prospects to say yes often enough that you can, with a straight face, claim early product-market fit.

Phase 2: Founder-led sales at scale (sort of)

Congratulations — you’ve actually got revenue and real customers. Now what? This is the moment most founders get carried away and think, “Right, time to hire a ‘proper’ salesperson so I can finally get this off my plate.”

Don’t. Seriously. Not yet.

You are still the best bloody salesperson in the entire company. You know the product, the vision, the customer pain, the whole messy backstory –   all the stuff no outsider can fake.

What you don’t have yet is process. Or leverage.

That’s the job now: stop winging it and start building something repeatable, so one day someone else can take this off your plate without crashing the bus.

This is the point where most founders properly cock it up. They carry on winging it – the same scrappy, seat-of-your-pants routine that got the first ten deals over the line – then act shocked when the pipeline flatlines or the first hire can’t close a window.

If you keep relying on instinct and adrenaline, you’ll be stuck in founder-hero mode forever. And founder-hero mode does not scale.

So now you build the scaffolding. A basic sales process. A CRM you actually use. Decent outreach and demo templates. A few metrics that tell you what’s working instead of what you hope is working.

It doesn’t need to be pretty – just repeatable.

You’re still doing most of the selling, but now you’re doing it systematically. Track your pipeline religiously. Know your conversion rates at each stage. Understand your sales cycle length. Start segmenting leads by quality. This isn’t about being a sales ops nerd (yet) – it’s about creating enough structure that someone else could follow your footsteps when the time comes.

Your goal in phase 2:
Turn “I somehow close deals” into “here is the rough sequence that reliably closes deals with this type of customer”. If you cannot document it, even in bullet points, you are not ready to hire.

Phase 3: Hiring your first real salesperson (and not screwing it up)

You’re finally ready to hire your first real salesperson – an account executive who can actually run a deal from hello to signature. And this, right here, is where many founders manage to set their own hair on fire.

They go too senior: the £200k-a-year VP Sales who wants to “build a team” when the team currently consists of… you.

Or they go too junior: bright-eyed grad who couldn’t close a window let alone a high-value sale.

Some go completely sideways: hiring an enterprise heavyweight when you’re flogging to SMBs. Wrong background, wrong motion, wrong everything.

The outcome is predictable: six months of pain, a cratered budget, and you – exhausted, skint, and muttering “why does nothing bloody work?” – back doing all the selling yourself. Back to square one.

And for the love of God, stop falling for charm, swagger, and shiny CVs. You want evidence. Deals closed. Targets hit. Real numbers. If they can’t show you receipts, they’re not your hire. 

When I hire anyone (not just sales roles), I always look for people who have spent two or three years at the same company and been promoted two or three times. I f*cking love them. Find one of them for you. They still need to be the right fit for your customers and your business, of course, but finding people motivated to succeed is priceless.

But you’re not stepping away yet. Your first salesperson isn’t replacing you; they’re multiplying you. You’ll still be closing big deals, coaching them on every call, and course-correcting constantly. Think of yourself as player-coach, not retired athlete. You’re building a sales culture now, not just filling a headcount.

Your goal in phase 3:
Prove that a non-founder can follow your process and close deals at an acceptable cost of sale.

Phase 4: Building a small sales team (without losing your soul)

You’ve got one salesperson smashing it. Great. Now it’s time to add another. And maybe another after that. You’re not just “doing sales” anymore – you’re building a team. This phase is all about replication: can you take whatever magic worked with salesperson #1 and recreate it with #2 and #3 without the whole thing turning feral?

And this is another point of danger for founders. They hire too fast and the quality falls off a cliff. Or they create a Wild West where every rep is doing their own weird interpretation of “sales”. Or they swing hard the other way and micromanage every email until the reps can’t breathe.

Both extremes are stupid.

What you want is structure that keeps everyone aligned, without sucking the personality and skill out of your salespeople. Same stages. Same milestones. Same basic process. But enough freedom for each rep to sell in a way that actually works for them.

And now you’re bumping into real sales leadership. Not just doing the deals – setting the pace, running proper pipeline reviews, coaching performance, fixing bottlenecks before they blow up. You’ll still jump into the big deals (and you should), but your role is shifting. Less and less playing. More and more coaching.

Your goal in phase 4:
Turn sales from heroic effort into a predictable system.

Phase 5: Hiring a sales leader (finally)

Right then – now you can hire a Sales Director or Head of Sales. But don’t kid yourself: this is not the moment you stroll off into the sunset. Delegation is not abdication. A sales leader doesn’t remove you from sales; it just means someone else is running the machine while you stay plugged into strategy and the deals that matter most.

The right sales leader at this stage is a builder – someone who can manage the team, sharpen the process, scale the operation, and bring predictability into the chaos. That frees you up for the important stuff: product, partnerships, fundraising, and the big enterprise wins.

The wrong sales leader? The one who rocks up wanting to bulldoze everything you’ve built, stack the team with their mates, and freeze you out of your own revenue engine. Avoid those f**kers at all costs.

When you hire, match their experience to your stage. If you’re at £2M ARR, get someone who’s taken a business from £2M to £10M – not someone who’s only ever played the £50M+ game. They’ll be bored, frustrated, and utterly useless.

Your goal in phase 5:
Make more than three sellers successful at the same time. Then you can hire a leader.

Phase 6: True founder-sales leverage (without kidding yourself you’re done)

Welcome to the final phase – the one all founders fantasise about but almost none actually reach. You’re no longer stuck in the day-to-day grind of selling. You’ve got a Sales Director running the engine, a bench of salespeople hitting quota, and a revenue machine that finally hums without you yanking every lever.

But let’s be clear: you’re not done with sales. You’ve just moved up a weight class.

Your job now is founder-led sales — the stuff only you can do. When we scaled Rackspace and Peer 1, the deal sizes went from £99 a month to £50k, from £249 a month to over £1m. Those leaps don’t come from salespeople following a playbook. They come from the founder sitting across the table, looking a customer in the eye and effectively saying: “yes, this is a stretch, but trust me, we’ll pull it off”. Salespeople sell what you tell them they can sell. Only the founder can bet the farm, even if it’s not quite the same as putting your mortgage on 0 at a roulette table. Only the founder can carry that level of risk, tell the story, and unlock the deals that change the trajectory of the business.

The best founder CEOs never “leave” sales. They evolve. They stay close enough to keep the company honest, relevant and growing. They set the vision, kick open executive doors, close the seven-figure stuff, shape the market they want to win, and make sure the sales team doesn’t drift away from the strategy. 

If you want to be the founder who actually pulls this off, you stay in the game – just on the deals and decisions that move the needle.

Your goal in phase 6:
Hire someone who can scale what already works. You stay involved as owner of the revenue system.

There is no handoff

You’re never actually done with sales. Not ever. The job changes shape, the leverage shifts, but founder-led sales runs from the first shaky “please buy this” to the day you sign the exit papers – and even then you’re still selling the narrative that gets the deal over the line.

So stop pretending there’s a clean handover moment coming. There isn’t. Build the process. Hire people who can actually do the work. Coach them hard. Stay visible. Lead the bloody thing.

Your revenue – and your sanity – depend on it.

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Written by business coach and leadership coaching expert Dominic Monkhouse. You can order your free copy of his new book, Mind Your F**king Business here.