The Saleship Enterprise


Enterprise.  To explore strange new worlds.
To seek out new life,
And new civilizations.
To boldly go where no (wo)man has gone before.

OK, shameless homage to one of my absolute favorite shows of all time, and totally applicable to the strangely elusive, ever confusing and hugely rewarding enterprise sale.  

This moniker, the enterprise account, is widely misunderstood and misused.  Sort of like the term coaching.  Is it really an enterprise account or just a big logo where one is selling to a small corner of the “starship”?  Merriam-Webster defines Enterprise in a variety of ways.  Interestingly enough, all of them apply to what’s in store for and what’s expected of today’s enterprise sales professional!

Let’s investigate further…

1 A project or undertaking that is especially difficult, complicated, or risky

Let’s face it.  The first thing that qualifies the Enterprise is that it’s big!  Just like our fave spaceship with lots of decks and rooms and technology and process and…people!  Glassdoor defines the Enterprise Account Manager as sales managers and account executives who manage key accounts that generate significant revenue. Well, duh?  I like Webster on this, because these are big honking companies (or spaceships) that have lots of connecting and sometimes conflicting cultures, and in many cases, conflicting goals and values.  It may have a single mission statement at HQ, and let’s face it, we are talking about human nature here, missions can be personal, so the idea that divisions can conflict with that mission and each other is not uncommon and not unthinkable.

2a A unit of economic organization or activity especially  : a business organization

Enterprise accounts are big.  Yes, and there are usually numerous moving parts, namely various autonomous business divisions, many with their own executive structures, ultimately reporting to a corporate headquarters that has its own hierarchy and identity.  So these business divisions or units can be within the same walls of the organization and also located in different and dispersed locations. One thing holds true here: they are a business organization and they are there to make money either for themselves or their stockholders.  All those value propositions that are drummed into your head still apply here, plus a few others you normally don’t consider like political upheaval, global trade challenges and the newly minted ESG.

b   A systematic purposeful activity

This is so important and a critical first step.  To build your route, navigate successfully and conduct business, you need a map with various views of all the levels of this labyrinth: personnel, geographic, marketplace, client base, sometimes cultural and political, and more.  You will most likely have to build that map yourself. When I see Webster’s definition here it’s what comes to mind:  You have to create a process and a rhythm with how, what and why you are reaching out, creating relationships, and examining the possibilities to conduct business together on a long-term basis.  And, don’t forget how, when and who you will lead to assist in engaging these alien life forms, never before discovered in some cases.  Technical teams, sales and executive leadership, partners, legal and financial departments could all play a role here.  And outside the Lone Wolf persona, most sales professionals will need to embrace the team here.

3  Readiness to engage in daring or difficult action : 

I recently attended the Celebrate: The Reality Road Show conference hosted by  As I am always looking for data and analysis of all things client and sales, a few factoids stood out to me.  1) Finding the decision maker in an enterprise account is almost three times more critical than a transactional account. Erosion of the opportunity climbs to 233% when the decision maker is not found and significantly involved.  2) Multi-threading is critical in an enterprise opportunity.  The more people you involve in it, the chances of successfully attaining an agreement go from 13% to 161% by just the second call! 

We have to be daring and call people we don’t know and who might not know us! (GASP!) We have to devise different strategies that can be difficult and sometimes painful; we have to herd cats into the enterprise corporate corral to get all heads nodding together.  This is a slog in many cases.  The elusive unicorn-like bluebird sale is out there and I’ve witnessed it a few times in my long career.  Usually due to an acquisition or a compliance violation.  Otherwise, this is a journey, and not for the journeyman.  One must be ready to go, be well provisioned and have your leadership onboard for the excursion. Because it’s not just the destination that is lighting you up and enticing you, mesmerizing you to dreams of incentive trips and MVP awards on the main stage.  You’ll need to know all the routes that can be chosen, essentially the direction you must take to keep moving to Valhalla.  Happy ears and lousy peripheral vision have been the end of many a salesforce pipeline buster.  GOAT to goat in just a mere phone call is a reality.

There is so much to share here and plenty of sales and coaching gurus to give you the what’s what on the Enterprise. When done right though, it is one of the greatest events a sales professional can be part of the successful, closed-won enterprise agreement.  The recognition, sense of achievement and let’s not forget the commission are just about as good as it gets in this career.  And…when done right, really creates change in your client’s world. You can truly make a difference for their benefit, their future! And that’s what a true Enterprise Sales Professional is all about.

Captain Kirk says at the end of a successful adventure, “Mr. Sulu, chart us a course.” To which his charge replies, “Where to Captain?” “Out there, that-a-way,” orders our fearless leader.  OK, a bit swashbuckling and…DARING!  Engage my brave sales friend.  And bring snacks.

I challenge salespeople to become sales professionals.  I guide managers to become leaders.”  Welcome in 2022 with the wild idea of investing in you!  Here’s a link to start creating that discussion right now!

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