As a startup at the expansion stage, there’s no doubt in my mind that you will look towards the enterprise market if you haven’t already. And for good reason… there is big business to be done there!
However, as an enterprise sales person for over 20 years, I’ve got to tell you — you really only get one shot at this market. Enterprise accounts have the attention span of a gnat… if you tank it on the first go, well, you’re more or less done.
I want to help you avoid that… because you can succeed at this level if you do the right work.
So whether you are just investigating enterprise sales or are already getting after it, here is the enterprise selling process and the specific techniques that have personally helped me close $100MM+ for companies selling anything from consulting services to HRTech SaaS products.
Start with the right mindset.
Imagine walking into a tailor to get a custom suit made of the finest Italian silk money can buy and having him pull a pre-made jacket off the rack, hold it up in front of you to check for size, and take you to the register.
You’d walk right out of there, wouldn’t you?
You didn’t go there for something that was made to fit everyone… you came to him because you need to look like the sharpest person in the room and you know that fit is 90% of making that happen.
Sadly, this is exactly how most startups treat enterprise-level clients and where most kill any chance they ever had.
See, at the enterprise level, the risk of buying into the wrong solution is MASSIVE for your buyers. So they need to make absolutely sure your solution is right for them before they pull the trigger.
That’s why the most critical thing you will ever do in your enterprise sales process is to get your mindset right. Enterprise deals are big, time-consuming, and driven by quality, not quantity.
They are high-touch, discovery-driven marathons — not a single shot to the finish line. You’re dealing with an average of 6.8 decision makers on deals that often take 12–18 months to close.
But most importantly, they are about fitting a custom solution for each buyer, not trying to fit a customer into your existing product. The perceived risk of purchase for a buyer at this scale will simply be too high without some level of customization in both your sales process and your product.
Yes, this is a ton of work to execute on your end. But you must approach it this way if you want to reap the rewards that the enterprise market has to offer. I’ve never seen a single product or service in my 20 years that was a dead perfect match.
Know your buyers and their needs better than they do.
There’s a reason why the jokes of top comedians always seem to have big audiences laughing so hard they cry… it’s because they’ve done their research on their audience and know them well.
They spend months testing out their jokes on smaller stages and learning what works. So when that special set at Madison Square Garden happens, they can walk out on stage confident they will nail it.
That’s exactly the level of prep work it takes to win at enterprise sales too.
In fact, after getting our minds wrapped around the commitment that enterprise sales requires, getting to know who our buyers are and what they need is priority number one.
Here’s how I do that.
1. Calculate your total addressable market.
This is exceptionally important and deserves an article all by itself. Whether you’re starting from scratch or not, read this article to learn how to do this.
2. Select the accounts that are the best fit to start with.
The power of the pipeline is fierce in enterprise sales. Remember, this is the long game, so prioritize your time accordingly with the accounts that are the best fit from the beginning and be prepared to put a lot of irons in the fire all at once.
3. Get deep inside your prospects’ world.
Once you have your prioritized list of key targets to go after, I set up alerts on company and industry news for each. Things like acquisitions, announcements, changes, new business, and more. You want to be looking for things like:
- What’s happening in the marketplace?
- What challenges are they facing?
- What does Crunchbase, Pitchbook, their annual report, etc. say about them?
- What does their roadmap look like?
This helps me to stay on top of everything in their world. Nudge is one of my personal favorites for this.
4. Map out the organization and find common ground.
Figure out who you think will be involved in the buying process, who your buyer will be, who your influencer will be, etc. and start engaging with them. Just make sure that when you reach out, you’re adding value and that you stand out. I’ve written an entire article on how to do this with social media on Sales For Life. We’ll dive deeper into this in the section below.
Consult, don’t sell.
“Good salespeople sell lots of product, but great salespeople make lots of customers successful.”
– Mark Birch
The truth is, success in enterprise sales really comes down to one simple thing: your prospects need a solution and your number one goal is to help them get that solution.
But if you want a seat at the table with them, you have to bring something they can’t get anywhere else.
These buyers have competing priorities and are getting approached ALL the time. So once contact is made, you need to find new and different ways to add value to what they’re trying to achieve and stand out from the crowd in the process.
This is where your research and further discovery is SO important.
Questions are key — make them count, listen, adjust, pivot, and respond in earnest to hit their nail on the head. LISTEN, pay attention, look for the space in between that nobody else would pick up on and use that fill the gaps they have.
The better you do this, the more eager they will be willing to engage.
For example, at Indeed I turned the idea of a lunch and learn into an exclusive roundtable event with a mix of prospects and current clients on a specific topic that was helpful to them. I had one of my key clients moderate it creating a mega opportunity for meaningful follow-up post-event.
It was so successful and valuable for them that I signed deals shortly thereafter with people that were turned off to Indeed previously. The best part, my existing relationships saw an immediate increase in spending as well.
You don’t always need to do things this high touch and involved. It can be anything as long as it’s helpful and value added. Even something as simple as a book that addresses the key problem they’re solving or making an introduction for them with another contact so they can brainstorm best practices is effective.
But whatever you’re doing to consult and help, make sure it really delivers for your buyer — even if you don’t gain a thing from it right now. It’s like an investment account — you have to make deposits before you make withdrawals.
And the more you invest, the bigger the dream vacation you can take later.
When the ink is dry, your work is just beginning.
The enterprise sales process is a ton of work when you do it right. But while it’s tempting to sit back and kick your feet up when you’ve finally closed that huge deal, the best sellers know the hard work isn’t over.
In fact, the best sellers know that a signed contract is just the beginning… there is often so much more opportunity for further growth that is left untapped in the form of referrals and even further expansion of the solution you can provide for your clients.
Remember, this is the long game — stay on top of changes in their marketplace and in their trajectory. Be that trusted confidant they can come to when they have questions or the proverbial @#!$ hits the fan.
Finding new customers is usually 10x more expensive than keeping existing ones, so staying on top of the relationship long past the end of the deal is worth every penny.
But, there’s also something else to consider — you absolutely must keep your pipeline full at the same time too. What happens if your marquee client pulls the plug or that big deal you’re counting on backs out?
The most successful sellers become ‘go to’ authorities in their respective ‘spaces’. They find ways to continue being helpful, even if it doesn’t benefit them directly. They know being top of mind is the most critical component of their longevity and success.
It’s like I always say — what you put into something is absolutely what you get out of it.
The Key Takeaway
Enterprise sales is about crafting a custom solution to solve a single customer’s problems rather than giving them a “one size fits all” product.
It’s about putting your customer’s need for a solution above your need to make a sale.
This takes a ton of preparation, creativity, and high-level strategic thinking to pull off. But I promise you — if you start with that mindset and do the right work, the pay off will be well worth it.