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Can Thought Leaders Run the Marathon of Enterprise Sales?

Many authors, thought leaders, and speakers are very good at running their businesses transactionally. They’re great sprinters. It’s not that being transactional is a good or bad thing; it’s the nature of the business they are doing. For example, as a speaker every speech is a transaction. The client has a date set, they either have the budget or they don’t, and they either book you or they don’t. These engagements typically can be consummated relatively easily. Once you’ve been hired to speak, you do a bit of prep, show up, and deliver the goods. Done deal.

Workshops and short term consulting work pretty much the same way. The client likes what you have to offer, they find the budget, they bring you in. Pretty straightforward, but a sprint nonetheless. A short burst of energy and effort are exerted and when the project is complete everyone goes their separate ways.

When it comes to large scale enterprise sales you need to be a marathon runner. It’s a very different set of skills and, in fact, if you apply your sprinting skills to this effort you may inadvertently kill a deal and damage your reputation in the process.

Let’s break down the differences into 4 categories:

  1. Time
  2. Number of “Buyers”
  3. Complexity of Contracting
  4. Things Happen


Getting your content into an enterprise level client at scale takes time. Typically, a good deal of time. Plan for 6 to 18 months. While this may be discouraging, it is actually an opportunity. Use that time to your advantage. Deepen the relationships you have with as many folks as you can inside the organization. Follow your client in the media, learn more about their culture, their business, and their industry. The mere fact that it takes such a long time is an advantage because most authors and thought leaders simply don’t have the patience to endure the lengthy process and move on to other things.


Number of Buyers

The number of folks involved in the buying decision is growing. In a recent article in HBR they noted that on average there are now 5.4 buyers involved in an enterprise engagement. There are a lot of reasons for this—from blurred lines between functions (training and IT, sales and marketing,) to companies doing what they can to insure they are making wise decisions. This is very different from using the “Old Boy’s Network” or getting a client to sign off on smaller deals that don’t have as much visibility or can come from a discretionary budget. You’ll be dealing with more and more people that represent various constituencies in the client’s organization.

Complexity of Contracting

Let’s face it, getting a speaking engagement to contract is very straightforward. The standard agreements rarely run more than a couple of pages and the buyers and sellers are well versed in the process. Not so when it comes to contracting large scale engagements. Clients often don’t understand IP rights, or they will ask for onerous restrictions relative to non-competes, or their payment terms inadvertently put you in the banking business. There’s no easy way through this process; it’s messy and complex, but again this is an opportunity. Many authors and thought leaders bow out at this phase of the race due to frustration or lack of understanding of what the client actually needs to see in an agreement.

Things Happen

So you’ve put in the necessary time, developed some great relationships, and got your second wind during the contracting phase, congratulations. But wait, there’s more. Just as you are about to move forward the client has a terrible quarter, they get acquired or acquire their largest competitor, a new regulation is passed that impacts them greatly, the CEO leaves, there’s a product recall, bad press, or a crisis of some sort. Lots of things can happen that are beyond your control that can kill a deal that you’ve put blood, sweat, and tears into. Sorry; it happens.

While I don’t have a magical solution to guarantee you’ll win every deal or enjoy the process, I think it’s important that you understand why selling into a large organization is different and that you modify your strategy and your tactics so that you can win this very lucrative type of work, and win it often.

Peter Winick has deep expertise in helping those with deep expertise. He is the CEO of Thought Leadership Leverage. Visit Peter on Twitter!

This Post Has One Comment

  1. Hi Peter,

    I like your advice to embrace the length of time it takes to cultivate enterprise sales.
    Thinking about your observation around short attention spans for some thought leaders and contrasting with the lessons of good social business, the long lead time is good for both parties.
    Quick sales are like blind dates: inauspicious for long term relationships.
    On the inside, the long lead times can be excrutiating, maddening and soul destroying. There always seems to be someone with yet another box to tick.
    Whatever the case, good advice. If you’re going to take on enterprise clients, make sure you have some smaller clients to keep your cashflow alive.

    Thanks again for the great content,


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