To Win Enterprise Customers, Think Like A Strategist

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Fresh insights can be found by linking enterprise customer acquisition to proactive corporate strategy activities. Our experience reinforces the potential benefits of engaging a strategist to quarterback or coach enterprise selling efforts.


This Strategy Lab considers the selling benefits of leveraging and thinking like an Essential Strategist when undertaking enterprise selling efforts.



First, a definitional construct.  Many companies define their markets as ‘enterprises.’ This definition is, in part, intended to establish an aspiration that the organization has an offering worthy of a large customer. In some cases, ‘enterprise’ is meant to differentiate from a small / medium business (SMB) segment that is considered different.

Very good things come from enterprise focus, and much good can come from considering a company’s offering in this context. There are also some big concerns and accompanying baggage that may come from targeting and landing an enterprise account.

For now, let’s assume that the enterprise account is a well-considered and advantageous target. We offer the following counsel to those companies pursuing their first, or tenth, or 100th enterprise account.

If you’ve got a corporate strategist, use that resource. If you don’t, think like one.

Strategists can frequently act as a proxy for the sophistication and analytic rigor that will be seen in enterprise IT groups and purchasing departments.

The goal, in many cases, is to position the company in a league just beyond current grasp. It’s a play in sophisticated positioning and thinking that often benefits from an outsider’s objective support

Moving forward, the right boots-on-the ground strategist or sales leader can push a process familiar to him/her, maintain the focus of senior leadership, and coach / teach the other players along the way.

Think like a deal team.

Enterprise customer acquisition is similar to M&A work:

  • It’s exhausting, and stretches teams and time frames beyond accustomed boundaries.
  • The sales effort, and prospective implementation, frequently require a new set of skills and responses that are beyond smaller markets and, usually, existing teams.
  • Early in market entrance, companies need to develop and refine responsive material that can be re-used.
  • It’s possible that this is an RFP response situation. If so, it’s a really great — and almost mandatory — time to consider a bunch of items around pricing and costing (pricing waterfall activities). See our discussion here.

Part time efforts will deliver part time results. Putting a deal team in place, and enabling that team to coordinate efforts throughout the company, substantially improves success rates.

Really ponder pricing and value.

In more cynical moments, our definition of enterprise intersects with aggressive purchaser segments. Enterprises are certainly not the only buying groups that can play hard ball. But, they are professionals at it. Smaller companies can avoid becoming grist for this mill by avoiding – as best as possible – these classic pitfalls:

  • Aggressively using price in an attempt to gain entrance to a situation that they a) may not fully understand, and b) are very likely not to realize.
  • Under estimating the a) time and resources necessary to participate in the buying process, and b) the implementation process and associated investments.
  • Assuming that follow-on work will make things right, only to find out later that every sales process is an event unto itself.

Our experience is that positioning value will be a real challenge: It always is, even for the most persistent and optimistic teams.  The prospective buyer may establish a grinding approach to the entire process that — unintentionally perhaps — favors incumbents or larger competitors. Uncharted territory and uphill chases are fine, but in moderate and digestible amounts.

These mistakes are avoidable, and costly to make — so get some experienced eyes and hands to build, evaluate and present the company’s case — to the prospect and inside the company.

Get everyone’s input.

We often see compartmentalized approaches to enterprise selling. Yet, if the project or account is won, success is dependent on the entire organization. This is such a truism that it could be an adjunct to the enterprise segment definition: The company will succeed only together!


Effective strategists, by nature, training and hard lessons, know to reach deep into the company, collecting input and assessing the potential impacts.

And, they are good at engaging senior leadership throughout the entire process. It takes patience and hard work.


Final Thoughts

As an example, our work in automotive retail familiarized us with a lot of companies dependent on capturing – and making good on – OEM relationships. Automotive OEMs go about choosing and influencing their supply chains in very different ways than individual dealerships or even sophisticated dealership groups. Their processes will appear – for self-serving reasons – to be lumbering, maze-like, unfair and hierarchical, all at different times and probably for specific reasons understood only to them. While appearing to offer impressive opportunities, enterprise engagement in this sector brings substantial risk to unprepared companies.

Many organizations eager to expand through enterprise development in other industries face similarly sized influencers and potential customers. In these situations, the strategist truly becomes essential to realize a positive return on the investments that are required.

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