It’s a frustrating tale, but one I bet lots of founder CEOs know only too well. You’ve got an amazing sales rep who is smashing every target they’re set. Month after month, quarter after quarter, you see their figures and know that they could probably even sell sun cream in Newcastle.

So you do what seems sensible. You get a team in to support them. Let your sales guru ‘focus’ on the big deals, sit back and wait for the sales to keep on growing.

Then crickets.

Six months pass, and the next thing you know, the sales development reps have nothing to support. The pipeline has run dry. Your outbound sales efforts are crumbling around you. And it was your fault.

You outsourced your salesperson’s biggest skill. The ability to generate leads for themselves. And now they’ve pretty much forgotten how to prospect and you’re starting from scratch with an empty sales pipeline and a demoralised workforce.

I tell that story from first-hand experience, but it comes with a message of hope. Outbound sales isn’t dead. But your pipeline generation is probably on the crap side so your sales process is never going to get going.

This is how to fix it.

Pipeline dreams

Sales pipeline generation is about spirit. To paraphrase Rocky, it’s not about how hard you can hit, but about how hard you can GET hit, and keep moving forward. There will be rejection after rejection after rejection. It’s how people respond to it that tells you the most.

Picture a dejected sales rep slumped in their seat at 4pm (I’m sure none of us are having to use our imagination too much at this point). They’ve made nineteen calls. No-one has answered. No-one has called back. The CRM is full of ‘left voicemail’ notes and bruised optimism.

The 19 ‘failures’ don’t mean a thing when it comes to determining whether this sales rep is good, bad, or mediocre. What matters is whether or not they make the twentieth call. After 19 rejections, the grit that it takes to reach for the phone instead of the whisky tells you everything.

It’s important because founders often wildly overestimate the quality of their pipeline generation strategy. They know their product is great, they know it solves problems like nothing else can, and they just expect others will see that immediately. They get a CRM tool, automate a few sequences, call it lead generation, and sit back expecting marketing to bring in a stream of inbound leads while the sales team sip coffee and high-five each other every time they close another huge deal.

When you’re hiring sales reps, talk to them about their worst ever spells. The times they missed target, the times no-one would take their calls. If they’ve been through it at least once and come out the other side with their enthusiasm undimmed, snap them up. Any good sales leader will tell you that these are the people who will drive consistent pipeline generation for your business.

Concentric circles: start warm, go cold

Sales. Like all aspects of business. Is centred on trust. And the more you know someone, the more likely you are to trust them. If you needed someone to look after your kids for an hour, you’ll take them to a family member or a friend, right? You wouldn’t knock on random doors and ask the first person who answers if they could stick the bairns in front of the telly for a bit, would you?

So why do so many founders assume that business relationships are different? Their first instinct when it comes to sales pipeline generation is to purchase an email list consisting entirely of strangers and then bombard them with cold emails in the hope that they will all magically fall into their carefully constructed sales funnel.

It won’t work. It never works. Why would you not start with people who know you, trust you, and probably even love you (a bit)?

Think of it as a circle, with you at the middle. Start with the people closest to you, and move steadily out.

Circle one: Your personal network

These people will take your call. You won’t need to negotiate your way past a receptionist or an EA; you’re straight in. Your conversion rates here might be thirty percent. You’d be mad to ignore that, especially when starting out.

Circle two: Your investors’ networks

These people might not know you well enough to trust you. But they know people who DO know you well enough to trust you. Portfolio companies, board connections, founder communities. These are places where you will get warm welcomes from people with credibility.

Circle three: Customers of your customers

These are potential customers only one degree removed from you. A familiar name and a shared contact goes a long way towards securing that initial conversation.

Circle four: Geographic proximity

It’s easier to be relevant when you’re talking to businesses who fit your market and happen to be based near to you. It’s also easier to take networking and prospecting away from the keyboard and catch up at a local event, over a coffee or whatever. This is also where social selling can work particularly well. A comment on a local business post or a shared connection at a regional event can open doors that cold email never would.

Circle five: Cold outreach

Ok, now you’ve exhausted every other option, it’s time to give cold outreach a try. Out here, you might well find that conversion rates are only around three percent. That means cold outreach isn’t scalable because it’s an inefficient way to build a sales pipeline or generate qualified leads. For b2b sales especially, cold outreach should be the last resort, not the first. On the plus side, it is a quick way to annoy people you haven’t even met yet. So there’s that.

Following this process saves you time and money, but it also gives you some valuable insights as you go. You’ll become clearer about your target audience, the pain points you’re addressing, and who your key decision makers actually are.

Prospecting is a team sport

Generating a sales pipeline can be a long, slow, lonely trudge. The key to winning at it is to make it an important, communal event.

I advise the founders I work with to make sure their sales teams dedicate one day a week to prospecting. Usually, it’s a Tuesday as that sits well in the rhythm of the week, but every business is different. The day doesn’t matter. The dedication to it, however, does.

It should be the sole focus of the day. All the other things that need doing. meetings, demos, admin. Can be scheduled for other days.

Blocking out the time is only half the reason this approach works. The rest is down to the shared energy it creates. When sales teams are working on the same project, in the same room, at the same time, they become far more effective than each of them doing the same thing alone.

They feed off each other. Small wins are celebrated when someone secures a big meeting and rejections feel lighter when shared with others (‘That’s the third time I’ve been told to bugger off this morning’).

The pipeline generation passport

Of course, you can’t just rock up on a Tuesday, sound an air horn and declare ‘IT’S SALES PIPELINE DAY, PEOPLE’ with the enthusiasm of a children’s TV presenter. To make it work, you need preparation. And that’s where your sales and marketing teams need to work together.

Every Friday, at noon, marketing should deliver a ‘PG passport’ to the sales team. It should be a document containing all the relevant news from that week, company announcements, funding rounds, job postings and industry development for the target account list.

It’s a homework document. Research. When Tuesday rolls around, the sales team aren’t wasting their breath spouting generic observations and platitudes. They should already have specific, relevant hooks for every prospect’s business on their list of calls. That’s what makes sales outreach work.

Note that I said ‘relevant’, not ‘personalised’. Using relevant customer data is what gets replies. If you’re calling because you see they’ve appointed a new CTO and you’d love to talk to them about how your software could save them millions on a specific workflow you know is a problem, you’re getting an appointment. If you just point out you notice you both went to the same university and that you both play golf according to their LinkedIn profile, then the best you can hope for is a restraining order.

Valuable insights beat pointless small talk every time.

The 30% rule

I have a rule that early account executives should be dedicating around thirty percent of their time to generating new pipeline. This is the foundation of a healthy sales process. Whenever I work with a founder who complains to me that their sales reps ‘don’t close enough’, I usually find that they’re spending ninety percent of their time working existing deals and the remaining ten percent prospecting. It’s never a surprise then, that the sales pipeline is dangerously thin and that future sales are at risk of dropping off a cliff. No pipeline means accurate sales forecasting is impossible.

If your reps aren’t sourcing between thirty and fifty percent of their own opportunities, your company will fail. You need full-cycle selling, where a rep generates their own sales pipeline, does proper lead qualification. Including qualifying enterprise prospects. And then closes deals. That’s non-negotiable until you reach significant scale. Without it, your sales process is hamstrung from the off.

The myth here is that salespeople should be fed a never-ending line of high quality leads from marketing. It’s bullsh*t. And dangerous bullsh*t at that. Marketing’s job is to build brand awareness, run content marketing, and to create inbound interest. It’s not to deliver a steady stream of qualified prospects to your reps’ inboxes. Founders that don’t get that tend to find their company in big trouble pretty quickly.

It’s good to talk

Bob Hoskins had a point back in the 90s. It really is good to talk.

I know what you’re thinking. No one answers their phone any more, cold calling is dead. LinkedIn and email are where its at, and the closest most people come to a phone call these days is a voice note.

Bollocks.

Fifty percent of outbound demos can still be booked over the phone. All it takes is the skill to handle the conversation, and the courage to pick up the damned phone in the first place. It forces a real conversation. The prospect can’t ghost you or forget to get back to you. They either want to talk or they don’t, and you have an answer one way or the other in 90 seconds flat.

The reason people say cold calling is dead is because they’re crap at it. They read from a script with all the warmth of a ransom, or they waffle on about the weather so their sales pitches feel generic. Most importantly, they don’t give the prospect a compelling, relevant reason for the call within the first fifteen seconds. Train your reps to do that, then give them a clear value proposition linked to specific pain points, arm them with the right tools to follow up every conversation, and the rest will take care of itself.

The founder’s card

As the founder, you always have a card up your sleeve that no sales rep can play. However good they are. You ARE the business.

When a founder calls a prospect, they take that call more often than not. When a ‘business development representative’ tries the same thing, you’d be amazed how quickly a prospect can find something else requiring their urgent attention.

The title of founder buys attention. It says to the prospect they are not part of some mass communication spray-and-pray operation. It tells them that the person who built the company thinks they are important.

Use that.

In the early days, you should be doing all the sales yourself. Walk the entire sales journey. Make the calls, write the emails, do the demos, and engage prospects at every stage yourself. You won’t be doing it forever, but you do need to understand what works so that you can build a sales strategy you can teach. And even once you have a sales team, you’ll still be needed for the deals that really matter.

The three sentence email

Founders write short emails. Salespeople write long ones. Guess which ones get read.

Your cold email should be three sentences long. Four, if you’re feeling particularly verbose. If they can’t read it on a mobile phone without scrolling, they’re not reading it. State the problem, state the relevance, ask for their interest, done. You’re a busy person, emailing another busy person. Write like it.

Creative outbound: Things that do not scale

When you’re starting out, the most effective outbound tactics are the ones that are impossible to scale. The bottle of champagne sent to a director who just raised funding, the handwritten notes, the personalised video messages.

They’re brilliant, they’re effective, and they cost a fortune. When your target is to book fifty meetings, these touches are your competitive advantage. Fast forward to a target of five thousand meetings, however, and you’re going to need a huge champagne budget, a professional forger on the books, and a film studio you can never leave. At some point, the game has to change, and you have to change with it.

The reverse sort hack

If you have any kind of self-serve product or free trial, there is one outbound move with the highest ROI of anything I’ve ever seen in sales.

Sort your user base by usage volume, descending. Find the companies that have quietly bought twenty or fifty seats without ever speaking to a salesperson. Then call them.

These are the warmest leads you’ll ever get. Intent is proven. They’re already paying customers. You’re ringing to make their experience better, expand into other teams, or have an honest conversation about pricing.

This is where customer success teams and sales teams should be joined at the hip. Customer success sees the full experience. Sales sees opportunity. If your customer relationship management setup is working properly, you’ve got detailed insights on usage patterns, expansion signals, and even website visitors sitting in your own customer data that most companies never bother to analyse.

Stop chasing strangers. Call your existing customers. They already love you.

Building an outbound sales process that never runs dry

Sales pipeline generation isn’t a hack, a tool, or a sequence you can automate and forget about. It separates the founders who build something lasting from the ones who wonder what went wrong six months after their best sales rep stopped picking up the phone.

Everything in this guide comes back to the same truth: the fundamentals of a healthy outbound sales process are not complicated, but they do require commitment. Work your circles. Give your sales teams the time, the intelligence, and the shared energy to prospect properly. Make sure your sales and marketing teams are genuinely aligned. Not just friendly when it comes to Friday night drinks. Use the founder’s card while you still can. Write the short email. Pick up the phone. Call your existing customers before you chase a single stranger. And when your pipeline generation efforts start to pay off, don’t make the mistake of outsourcing the thing that made them work in the first place.

The pipeline doesn’t fill itself. But build the right habits, the right team, and the right sales process around it, and it will never run dry again.

Book a free discovery call with Dominic.

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.