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Everything you need to know about enterprise sales, but were too afraid to ask

Posted on: December 8, 2021

Reading Time: 6 minutes

Category: B2B sales

Everything you need to know about Enterprise Sales, but were too afraid to ask

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It’s obvious why you would want to start enterprise selling.

There’s bigger wins, bigger kudos and bigger long-term opportunities.

Yet, there’s a good reason that enterprise sales are sometimes referred to as ‘complex sales’. And there’s a good reason to enter the enterprise sales arena with your eyes wide open.

This beginner’s guide to enterprise sales will equip you with everything you need to know to kickstart your journey.

So, if you’re ready, strap yourself in – we’re about to hit warp drive.

‘Complex sales, the final frontier.

These are the voyages of the Starship Enterprise.

We’ll explore strange new accounts, seek out large opportunities and new revenue, and boldly go where our sales team has not gone before.’

James T. Kirk, Captain of the Enterprise

What exactly is an enterprise sale?


We’re going to kick off this quick guide to enterprise sales with a curve ball.


You do not actually have to sell to a large company to be involved in an enterprise sale.

We’ll wait for the dust to settle on that – and now we’ll set things straight.

Enterprise sales are any sale when the stakes are high.

It may be that your solution will deliver a massive business impact, will command a price tag that makes the eyes water, will span multiple years, will involve incredibly complex implementation or entail a lot of risk.

And, admittedly, at least one of these will pretty much always apply when the account sold to is of enterprise size.

What sets enterprise sales apart however is not the target account but the fact that they will involve buying decisions on a business-critical level that require probing questions to be answered, use cases to be demonstrated, multiple players involved in bids and even more decision makers than the usual sales.

Why should I care?

The heightened stakes of enterprise sales can often lead to ‘knock-on’ as well as immediate benefits.

Here’s the top three prizes to keep your eyes on:

  1. Build your brand credibility

In commercial terms, an enterprise sale is the equivalent of the geo-political ‘domino’ effect.

When one falls into your lap it lends you the gravitas and credibility to scoop up many smaller fish and probably another tuna or two.

  • Make yourself a comfy revenue bed for the future

Enterprise deals tend to not only be large but long-lasting.

Once in places they guarantee a consistent stream of revenue on which you can build from. They also place you in the driving seat for taking advantage of opportunities to up-sell improvements and extensions to the solution already lovingly put in place.

  • Develop a profitable partnership

Enterprise deals only really get closed when you add significant value into the mix.

As you increasingly demonstrate your value through the lengthy sales cycle and over the course of the lengthy contract you will build a profitable partnership with your accounts.

Sounds great. Anything else I should know?

 The benefits of enterprise sales can only be attained at a price: the stakes here are high and the hurdles to gracefully leap over are equally forbidding.

Here are the top three challenges that face those looking to explore the final frontier of enterprise sales.

  1. This is a marathon not a sprint

The main feature of an enterprise sale is that it can take a long, long, long, long time.

This deal will not be closed overnight: expect months of pitches, formal bids, demonstrations, use case testing, trials and even the kitchen sink being thrown at you.

It takes a lot of work from all your team – not just the sales people – to make this happen. And it doesn’t matter if your bath tub is half full or half empty – the plug could still be pulled at any moment.

  • The true decision makers can be hidden and after you’ve found them it’s a game of herding cats

Forget sales psychology – it will only get you so far. To win this marathon race you are going to need to understand organisational culture and behaviour, and not just theoretically but of the account you are pitching to.

There will be many stakeholders and decision makers and not all will announce themselves or be announced from the get go.

Even when you have flushed them all out it’s like herding cats to corral themselves all into a meeting or to marshal a unified decision from them.

And keeping that smile firmly fixed gets harder and harder as the process grinds on.

  • You’ll need a good milliner for all the hats you will have to wear

Unfortunately, you won’t just have to get everyone together, you’ll have to speak the language of the finance team, the tech team, the marketing team, the ops team, the legal team and so on.

You need to understand what each decision maker is looking for and make sure you give it to them in words they understand. To do this you are going to need to get the buy in and ‘singing off same hymn sheet’ harmony from your internal team – including Sarah who you stole the last teabag from.

In summary, in just two words, tell me what I need to make an enterprise sale

We’re going to have to think about that – can we get back to you?

<rustles papers, scratches head, glances to top left for inspiration>


Here it is:

A scalable solution.

(You’ll let us have the ‘A’, right?)


If you haven’t tested your solution at scale, you can’t play big.


Enterprise sales can never be replicable, because they are never exactly the same.

These are not your bog-standard ‘quick demo, looks good, there you go’ deals.

They are all about getting into each customer’s shoes and creating something bespoke that meets their specific business challenges, commercial environment and growth plans.

In this process you will be more of a consultant and advisor than a salesperson.

There – how did we do?

“There is a way out of every box, a solution to every enterprise sale.
It’s just a matter of finding it.”
Captain Jean-Luc Picard

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