The enterprise sales market can seem like a daunting world to enter as a founder – especially if you’re new to it.
Many founders solve this problem by hiring someone to sell for them.
And while this can work if you have the budget, runway, and make the right hire… the truth is, you’re better off doing it yourself before scaling a team.
Even if you’ve never done it before.
For example, a founder I talked to recently has spent the last 4 years doing all of the sales himself. He has the pricing nailed down, he knows how long it really takes to sell, what the buyers want/need/feel/etc.
This is priceless knowledge that will help him hire EXACTLY who he needs to take the baton and run with it later… as well as lead them to success in the future!
I talk often with my early-stage founder friends on how to do this… here is some of my best advice from my 20-years in enterprise sales that has helped them pave the way to success.
First things first… your mindset.
“Success is really about your mindset.”
– F. Gary Gray
This is probably the most important element to laying a successful foundation in the enterprise market.
How you approach your buyers and the mindset with which you do so is critical because it directs the approach you’ll take at every step of your sales process.
Here are the two most important areas to make sure your mindset is correct.
1. What enterprise sales is (and is not).
As wild as it may sound, something as simple as the way you define enterprise sales can make or break your success.
It’s nothing like selling to the SMB world… though many don’t understand to what extent.
I’ve written an entire article that breaks down the mindset of enterprise sales to use for success in this market (it’s linked above and something I’d strongly suggest if you haven’t spent much time in this market).
But at a high level, the difference between SMB sales and enterprise sales is this:
“Where SMB deals are all about finding buyers who want your existing product right out of the box, enterprise deals are all about crafting one-off, custom solutions for the biggest buyers.”
This difference is key… it creates a lot of additional complexity that will extend the sales cycle and energy required to close a single deal (think 6-18 months). So it’s important to set your expectations correctly and plan for this.
More importantly, it changes the way you should be approaching your buyers completely.
2. Don’t pitch… embrace discovery.
As founders, we start with a vision of how we want to impact the world and seek to make it a reality.
But that’s often a double-edged sword – sometimes we forget that feedback from our buyers is a gift.
The truth is, at the early stages of selling it’s not about convincing your market to buy something – it’s you hearing what they’re saying and taking that back to your team to make necessary adjustments (even if the team is just your co-founder sitting next to you).
You need to be willing to say “These big dreams we had about building this? People actually want THIS instead. How do we make that happen?”
That’s why the most important “thing” you’ll ever take to your enterprise-level sales meetings is not a well-crafted PowerPoint presentation, but rather your active listening skills.
As Chris Orlob and the Gong.io team showed with their research, good discovery closes more deals than the best closing technique ever could.
Your job early on is to uncover what your prospect’s business truly needs… and then find a way to make that come to life for them.
Common misconceptions founders often have about sales.
There is a lot of sales advice out there that is toxic. Some of it you’ll hear from others, but some of it you might be telling yourself.
Here are 3 I see most often that will hamper your success.
1. “Let’s just show them the product and they will lose their mind.”
If only it were this easy!
It is very rare (think unicorns, not snow leopards) that your product is going to be an instant winner for any enterprise buyer. I have yet to see a product that met the needs of an enterprise client perfectly without customization!
So approach each buyer with a desire to understand what they are facing from all angles. It will take a lot of work to get all of the key decision makers (typically between 6-7 people) on board.
The risks are far too great to expect instant, unanimous buy-in from them!
2. “Sales is a necessary evil.”
“Well, the joke is I started off in engineering and I literally remember saying to my co-workers, ‘I hate these salespeople.’ And every so often that quote haunts me.”
Many founders come from the product/engineering side and have had negative experiences with sales or salespeople. I understand if this is a battle you’re currently facing, you’re not alone.
But the truth is, the people who have shaped your view on this profession do not truly represent what sales is at all.
Alli McKee (founder of Stick.ai) explains this well in her video here:
The most successful companies don’t work with an “us vs. them” mentality. In fact, a siloed approach can lead to startup death.
It’s up to you as the leader to set the tone. As I always say, “it starts from the top down.”
3. “Let me just hire a salesperson and they’ll figure it all out.”
There will probably come a time (maybe it’s now) when the going will get tough and you’ll be tempted to hire someone to take this over for you.
Resist this urge until you have a repeatable process that you know works.
I can’t say it better than several other founders did in this article:
“I think the first thing is that as a founder you have to sell. I saw a lot of founders I know trying to skip that founder step. And they were like, “Let me just hire a salesperson and they’ll go out and sell.” You can’t skip that step. If you as the founder are not comfortable talking with customers, if you’re not comfortable with what your value proposition is, if you’re not comfortable giving a price. You don’t have anything to transition.”
“I think the mistake we made was we hired salespeople too early. I think ours wasn’t necessarily that we had a clear repeatable process and, “Now we need to scale this up.” It was more, “Maybe we should have salespeople,” for no real clear reason. Our board was like, “Should you have them?” And we were like, “I don’t know. Should we? Let’s go hire them.”
Remember, it is a lot easier to transition and grow a sales process that is proven to work on a small scale than it is to try to fix a flawed one further down the road.
Build a process you know works first before you hire people to scale it.
Your enterprise sales process as a founder.
One of the most common misconceptions about the sales process is that you can template someone else’s and apply it to your business to be successful.
Nothing could be further from the truth, especially in enterprise sales!
While you can take pieces and parts, the reality is your sales process shouldn’t look exactly like anyone else’s.
Their buyers aren’t your buyers
Their product isn’t your product
Their KPI’s aren’t your KPI’s
So start with a baseline approach and treat it like you’re discovering it along the way from there on out. You will likely not have it perfectly dialed in the first time and will need to refine it over time.
Additionally, be sure to document everything you do from day one. It will be very difficult to pass on the things you’ve learned to anyone you hire later if you haven’t.
Alright, let’s dig in!
1. Nail down your messaging.
While yes, discovery is the most important piece of what you need to do during the sales process, you’ll still need to have your value prop and associated messaging tight and clean.
My guess is you probably have a business plan or pitch deck – let that be your guiding force.
Focus on why you started the company and what you’re there to do. Nail your story down!
But, keep yourself from getting too far into the weeds. It’s tempting and easy to wax on and on and on about your ‘baby’ that you’re proud of, but you’ll do more harm than good if you take this approach.
You want to speak to your buyers’ needs, but not overwhelm them with self-promotional anecdotes!
2. Get a CRM system.
While it’s tempting to save a few bucks and wing it, it’s critical to stay organized. A good CRM will help you track all the pieces and parts you need to in order to keep an enterprise deal on track and will make it a heck of a lot easier to transition once you’re ready to hire.
There are lots of CRM’s out there (some more affordable and functional than others)… here are a few of my recommendations.
Copper – This is the CRM I use myself. I like it because it 100% integrates with Google/Gmail.
Pipedrive – Very affordable, easy to set up yourself (you don’t need a consultant), and comes with a ton of great features.
Hubspot – Gives you the core functionality you need from a CRM for free.
Each of these have the ‘legs’ to help you scale until you’re ready for a more robust system down the road.
3. Identify targets that you can engage with (prioritize ruthlessly).
After you’ve nailed down your messaging and are acquainted with your CRM, the next (and most important) thing to do is to dial in exactly who your buyer is.
Enterprise deals can take an entire year (or more) to close. And you don’t want to spend that kind of time and energy on a deal only to have it fall through because the buyer wasn’t the right fit.
So at this stage, it’s all about quality.
The better you select the buyers who can really use your solution, the more it will benefit you later.
Real need plus an excellent experience with your brand and solution creates positive reviews and powerful case studies you can leverage into the next deal. This is foundational to gaining traction in the enterprise market.
So make a pact with yourself and your co-founders right now to only work with those who are the best fit.
Also, a word of warning… don’t go after the biggest/best clients first. You don’t want to screw up your first/only chance to make an impression (this is a very real thing at the enterprise level… if you muck it up, good luck getting back in the door).
Instead, start with smaller prospects to nail down your process and create some preliminary results to benchmark from.
4. Engage your prospects with thoughtful outreach.
So you’ve got your messaging, your tech, and your targets… now it’s time to engage them!
There are many ways to do this and it will depend on your specific buyers. But here are some of the ones that have served me best over the years (including a few articles I’ve written that go into much greater detail on “how”).
Create or engage with online content.
There are many ways and places to do this… you can start a blog, guest post on other blogs, share on social media, comment/share other people’s content, and more.
Some of the places and methods that have served me best are in this article on social selling.
Whatever you do content-wise, make sure that it is high-quality and value-added. There is a lot of junk content out there and you must differentiate yourself!
Connect with prospects on LinkedIn.
There is a simple method I use to get the attention of nearly anyone I would like to engage with on LinkedIn. I’ve written an article about it here on the ATP blog.
Regardless of what you’ve heard, the telephone is very much still a viable sales prospecting tool.
Case in point, I used it to engage a client we ended up closing an 8-figure deal with!
Don’t be afraid to pick up the telephone and call… just make sure you follow a process similar to what I did via the link above.
Note, I’m not referring to mass email cadences here or emails that pitch anything. That has no place in enterprise sales.
Instead, I’m talking about highly-personalized, thought-provoking outreach.
Here’s a great example. Let’s say a key prospect just got Series B funding… most salespeople would send an email like this:
“Mike – I just heard the news… congrats on the Series B! So excited for you all. Do you need help building out your sales team?”
But the thing is… this is very assumptive. And self-serving. Who says scaling their sales team is even their first priority with this new funding? Or that they would consider you?
Instead, something like this is a much better approach:
“Mike – I just heard the news… congrats on the Series B! So excited for you all. What does this mean for your growth goals?”
Notice how the question is about him and what he wants to achieve. And how it leaves him room to say “no” without having to actually say it.
This positions someone who actually cares about what he’s trying to achieve, rather than someone who wants to sell him something… a critical difference!
5. Kick off with a discovery call.
Once you’ve engaged your buyer, you’ll want to set up a preliminary call to learn more about their problems, goals, and outlook.
This article does a great job of breaking down the important elements of great discovery calls from Gong.io’s data (which backs what I’ve learned from my years in the sales trenches).
However, there is one important point that I want to call out here… discovery should be continuous, not a “step” in the process.
This is especially important in enterprise sales because each deal has a lot of parts in motion at the same time.
If you’re not constantly doing discovery, it will morph and change and fall apart.
6. Establish how you will demo.
When it comes time to demo, the first item to tackle is to determine up front who will be on the call and what the goals for it are.
This should be directed by your discovery work, not something you cooked up and canned in a vacuum to regurgitate later. Otherwise, you’ll spend too much time talking at them rather than talking with them.
And interactive dialogue is what makes a demo great!
Before the demo starts, send an agenda asking them to fill in any “blanks” with topics they feel are missing.
And finally, make sure you end the time together with clearly defined next steps.
(For more on the details of demos, this article a la Sales Hacker is a great resource)
7. Focus on customer success.
You closed a deal… congrats! That is a huge achievement.
However, this is where I see a lot of startups make a big costly mistake by letting them go dark.
Don’t do this… it is 10x more expensive to get a new client than to keep one you have. So once the deal is closed, stay close to them and be ready to iterate based on their feedback.
Construct a success strategy based upon what you find/what they’re telling you to keep them happy and successful and look for other opportunities. The more entrenched you are within an account, the less risk you have of losing them.
Keep in mind, they can be evangelists for you in the future if you do this well, further aiding you in the sales process with other (bigger) buyers.
This quote sums up the one thing that is most critical to take away from this article:
“Stop selling. Start helping”
– Zig Ziglar
Successful enterprise sellers are viewed as trusted colleagues first and foremost. They never forget how important it is to be students of their buyers in order to understand how they can help best!
So approach your prospects as someone with this mindset (NOT to sell them something) and you’ll go much further.
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