How to do enterprise sales without doing "enterprise sales"

Enterprise Sales. It always sounds great in theory, doesn’t it?

Fortune 500 Logos + Enterprise Reps + Six Figure Contracts = BOOM!

But more often than not, the reality is quite the opposite:

• Lack of cross-functional alignment

• Legions of stakeholders

• Nobody willing to make the buying decision.

• Incumbent vendors with custom features and long term contracts.

• Packs of in-house lawyers after their pound of flesh.

• 25-page security questionnaires.

• The list goes on.

Yet every day another startup founder decides to stand up an enterprise sales effort:

“GUYS, we just closed MICROSOFT! $150k! Inbound lead! This is game changing! We gotta spin up an enterprise team and do more of this!”.

If you are going through this journey, let me share some tips to make it easier, faster and more predictable for you:

1. Find the innovation group. Most big companies are essentially a collection of smaller companies with varying degrees of operating autonomy. The groups with the most freedom are usually the ones tasked with dealing with disruptive market trends, which makes them willing to work with startup vendors. Here are 3 real-world examples:

   1) A company like General Motors, trying to get into a new market like electric delivery vehicles, will often stand up an independent business unit like Brightdrop.

   2) A traditional company like Walmart, going through digital transformation, will usually have a digital group like Walmart Labs, staffed by people who are close to the tech community.

   3) A holding company like Neiman Marcus Group will often have a brand like Last Call that serves as the proofing ground for new ideas before rolling them out to the larger brands in the portfolio.

2. Sell to individual departments. If you can sell into a single department (versus selling across the enterprise), you will always reduce the number of stakeholders to a manageable size and most importantly find a department head willing and able to make the buying decision. Obviously you need a product that lends itself to this type of sale; Slack and DocuSign are good examples of companies that have been successful with this strategy.

3. Fly under the approval radar. Most big companies have a tool that routes purchases for internal approval based on the amount—the higher the amount, the higher it needs to go. In many companies, anything over $100k triggers increased scrutiny, so finding out the threshold and staying under it pays dividends. The last thing you want is some ivory-tower lifer SVP having your $150k PO land in their inbox and start asking questions at the eleventh hour, so if your product costs more than $100k, split it across multiple orders. E.g. $75k now, another $75k in six months.

4. Simplify your contracts. I’ve seen 3 approaches work here:

   1) Ask for a standard vendor contract that you can just mark up with your product, service, fees and payment terms and have your lawyer see if you can live with it. I like this approach because you can compare terms across customers to see what is industry-standard vs egregious, and use the insights in your contract discussions. You can also decide whether to walk away.

   2) If you have to use your contract, make it as short as possible. The less you put in it, the less there is for the other side to react to, and (surprisingly) many in-house lawyers won’t bother to add in extra language. You obviously need a lawyer on your side who can a) create a simple contract and b) educate you on any risks you are taking by leaving things out.

   3) Reference your terms and conditions in the purchase order and have the user accept them as part of the onboarding process. Your buyer may then be able to get the PO approved without having to run it through legal review, depending on how buttoned-up their procurement process is.

5. Avoid legacy systems. If making your sale involves replacing a ten-year old legacy system, run away as fast as you can unless you have a C-level champion with the ability to push through the change. Otherwise, whatever initial excitement you create with your buyer will quickly wane as they start to realize that nobody fully understands the legacy system well enough to be certain something isn’t going to break

I hope these tips make your enterprise sales journey a smoother one. Good luck!

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