How to win ￡100k+ deals on LinkedIn

Can you really close a ￡100k deal from LinkedIn?

How do you even do that?

I've done this multiple times and my team have helped others do this too, so I'm going to break it down for you and show you what's involved.

Before I do, let me just say, the majority of LinkedIn advice you see about winning business from LinkedIn is total and utter tripe. It's from people regurgitating advice from other people.

Most have never done it.

I saw some advice recently from someone who teaches people how to sell $100k+ deals and advising people not to sell low ticket. Her advice was "stop selling low ticket!!!"

Hypocritically her offer was a $197 promotion.

My first ￡150k deal on LinkedIn actually started with a ￡195 sale. A try before you buy. This leads me to the topic of this article.

Lesson 1: It's easier to upsell than cold sell

My first big deal on LinkedIn was from someone who bough a ￡195 digital course. They loved it so much, saw the potential in it and shared it with their team. My big lesson is that if you are selling to large organisations a low ticket taster can be a great way to get buy in at an early stage.

Often the low ticket offers you make are a feeder for something bigger. So, this begs the question, if a senior exec bought your '￡195 thing' would you know how to move them to the next step?

Even if you don't know exactly right now, you should have a broad idea of how you can help if suddenly you get someone asking for a programme for their whole team. Remember, people expect to pay more for bespoke and personal involvement.

If someone pays ￡195 for your online thing, they will pay a lot more for a personal thing. Low ticket entry point deals can be great, as long as you have a plan to upsell them.

Lesson 2: You need champions

Without my champion it would have been almost impossible to close my ￡150k deal. They saw how it could help them and how it could help the company. They believed in it, trusted it and were prepared to advocate for it. In a corporate environment, which doesn't reward failure, getting someone to put their neck out for you is a big ask. They need to be fully bought into you and your idea.

This is about creating believers. People who ascribe to your viewpoint, your view of the world and your approach to the problem. This is why people buy in, they buy in because you have a stand on a problem, topic or opportunity.

People don't buy in to generic, vanilla and beige. Stand for something and build relationships on that basis. If you want a champion in a business that will spend ￡100k+ with you, they need to be convinced not just in your methods, they need to wholly buy into you and what you believe and stand for.

You need to stand for something, you need to believe in something. Vanilla will not cut it.

PS - An outrageous, wildcard personal brand is not the answer - this is about beliefs, not expression. I've seen how the bold and brash personal brands get swatted like flies in a corporate environment.

Why? Because nobody wants to take the risk to champion you.

Lesson 3: The money is in the Lurkers

The people on LinkedIn who are posting regularly are the money hunters. They are posting to get themselves out there. That's their primary objective. The spenders are the Lurkers.

Many of you are spending time liking and commenting on other peoples posts to increase your reach and engagement. Truth bomb - all the money, ALL THE MONEY is with the Lurkers. The people who don't post.

More than 100 companies who have spent ￡100k+ with me, I can tell you with certainty, the ones that drop the big bucks aren't posting. They don't need to and prefer not to. If you spend too much time on the people who post, you are prioritising your effort in the wrong places.

Lurkers infrequently post original content, often repost their company page posts and job postings. Lurkers like content and comment on content for their colleagues and people they know.

The advice you've been given to engage with their content is wrong.

The people who pay the big bucks don't post. The observe and consume.

Lesson 4: Multiple exposures

No, I'm not advocating you flash your personal parts. The big deals never come from cold, not on LinkedIn anyway. The number of times I get "You've been in my feed for a while now and...." is surreal.

Before someone messages you and asks for your help, they will consume multiple posts and (if you're smart) consume for of your interactive and long form content).

It's not one post or one message, it's a picture built up over time. I was speaking at a conference for Chief Revenue Officers last year and I got talking to a number of them. One question I asked was "how many touchpoints to win a deal?" The consensus was that it was more than 20 touchpoints to land a big deal.

How are you doing that?

Are you relying on your posts to do it?

Do you have a plan to create multiple exposures to your brand, your message and your offer?

I can tell you with certainty, relying on your posts, will leave you with a long wait.

Likewise, if you use messaging to do that, you'll be blocked way before you reach that magical 20.

It's got to be a bit of everything, short form (posts), Long form (audio / articles) and outreach (conversations).

Waiting for your posts to do that is crazy.

Lesson 5: Big pay off, big journey

Don't expect big deals to convert quickly.

If I'm working on a ￡3k deal, I'm expecting 3-4 weeks start to finish. When I'm working on a big deal, we are talking 3-4 months, sometimes even longer.

One of my client has been working with me at a low level for 18 months, in 2024, they increased their spend to ￡120k a year. They became one of my Top 10 clients in 2024, because since 2022, they have had great results.

Big deals take time.

In my business, we have two markets. It's tricky to do for most solopreneurs, but the benefits of a team allow you to successfully target multiple markets at once. My bread and butter is small businesses, my icing on the cake is corporates.

The reason: I can close 10 small business deals every week, but the corporate deals take time.

If I try to pitch big corporates a ￡100k+ deal, 99% of the time I'll be ignored. I have a strategy of how I engage high-value clients over multiple touchpoints. In many cases, I have no agenda to outreach for 6+ months. I want to build the awareness, relationships and belief BEFORE I ever reach out. I'm playing a long term game with my big deals, because I know, even if they did bite from a cold pitch, I have to build the trust first. Nobody parts with ￡100k+ without believing in the provider. So, I do as much of that as I can first. It' much easier to strike a conversation if I've done the prep work.

Once you get into the swing of big deals, you have a pipeline of them, at any given time, we have more than 30 big deals floating. You can't be reliant on one big deal, you need a pipeline of them, because naturally some will take longer than others to come to fruition.

Be patient.

Lesson 6: Gravity is on your side

It might sound disappointing that big deals take time. There is a flip side. The nature of high value deals is that they are considered analytically and evaluated without the emotion of a small business.

Big deals are often decided by people who aren't emotionally connected to the outcome or the expense. This means they think it through more carefully. If you've been selling to small businesses for a long time, you might find this frustrating, but it is a benefit. This means they are more pragmatic about the outcomes, more balanced in their decisions and as a result slower in making decisions.

This is a good thing. Big deals are rarely entered into rashly.

I've spoken to a number of people who sell to small businesses and solopreneurs and one of the big issues they face is the emotional connectivity to the services they offer. This can mean quick decisions to buy and quick decisions to disengage.

Despite what we see online, the promises of money while you sleep, the reality is, long term success doesn't come from quick wins and quick fixes.

In a big deal, the consideration period, the analysis is a good thing. It means clients go into a deal with you with their eyes open, they commit for a realistic outcome.

It also means, that your competitors have that barrier to entry. They need to go through the same hurdles to try to win the business. Trust and relationships are key to keeping those big deals over multiple years.

Lesson 7: ￡100k or ￡1k?

I'd need to close a hundred clients at ￡1k to make ￡100k or I could close one. If you're a small business reading this, you'll have a major problem closing a ￡100k deal because it may make you beholden to one client. That's 100% true.

That's why you need ten of them. If you look closely at how much it costs you in time and effort to win a ￡1k client, then scale that up, you'll quickly see, that you can do less marketing and make more money selling ten ￡100k deals, than a hundred ￡1k deals.

In my world, because I've built out a team, I can have the luxury of selling my Accelerator programme for solopreneurs and small businesses, whilst working on my ￡100k deals. In reality, if you're a solopreneur, it's hard to do both.

That's why it's important to know WHO you're selling to, it's VERY hard to sell to two different audiences, with different priorities at the same time.

For most people on LinkedIn, they shouldn't be selling thing less than ￡2k, as you hit the effort to reward ratio issue. You have to spend too much time on the platform to make it worth your while.

Are you looking to sell ￡100k+ deals on LinkedIn?

Let me know and I'll give you more details strategies to get you those deals.

PS - If you liked this, don't be a Lurker - like, comment and repost.