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You Can’t Sell into the Enterprise Overnight

Sales Process

My husband Chris wrote an article recently that paints a picture of a salesperson as the curator of the customer’s purchase experience.  As a professional buyer who has worked with hundreds of companies—from the largest to the fastest growing—having a person I trust, who can help me navigate both their organization and mine, is absolutely essential. You can access Chris’ article here.

Now, I’d like to offer a perspective on what it takes to be that trusted curator.

The first thing you have to understand is that no matter how many short-cuts and workarounds a company has in its arsenal—VC money, board connections, famous founders—you can’t sell into the Enterprise overnight.  If you want to work with the largest companies in the world, you will need stamina. I realize this can be frustrating for salespeople. Contrary to what you might be told, procurement people are not in the deal-prevention business. However, we are in the risk-mitigation business.

Remember—it’s taken years to build our brands. My first responsibility as the steward of the business is to protect it. While you might be able to reduce our costs by 25% or help us reach new consumers on Mars, smart buyers will not make rash decisions or take reckless risks. When a new idea surfaces, it cannot be realized without some amount of change—and change always, ALWAYS introduces some level of risk.

As the deal progresses, it may feel as if the excitement generated at the beginning of the sales cycle is gone forever. Have faith, though—it’s still there. If the process is suddenly starting to feel arduous, it usually means we are taking you seriously. We are carefully considering the benefits of your solution against all of the changes required to realize those gains.

When you are engaging with a large, mature enterprise and you set expectations that it’s a journey, your risk of burnout will go down measurably. In the meantime, here are suggestions that will improve your company’s chances of making it through.

RELATED: How to Close an Enterprise Sale in a Niche Market


Do your homework on our business. A public company shares the most intimate details of its businesses. Take the time to develop an informed viewpoint. Understand what problem you’re solving, how it typically shows up in our business and who has the most to lose or gain by solving it. I cannot tell you how even a little homework on our business will differentiate you from your competition.

RELATED: How to Help Your Sales Development Team Break into the C-Suite


Develop an approach for how you will uncover the evidence of the problem you want to solve and validate a buyer’s willingness and ability to solve it. Calculate the risks that your solution introduces and start planning on how to mitigate those risks.  Develop a timeline and action plan for how you will navigate your buyer’s organization, including the steps of the decision-making process. Have stops along the way to decide whether you should continue on or no longer engage in the pursuit. Don’t just share the plan with your own leadership to manage their expectations—share with your client or prospect to get them on the same page with you. Believe it or not, we also don’t want a buying process that lasts in perpetuity.

RELATED: Deal Breakers: Training Your Reps to Walk Away from a Bad Deal


Keeping the right level of energy throughout the pursuit can be a challenge. As a buyer, I don’t want to be taken to the altar on the first date—and I certainly don’t want you to become neglectful in the middle of the courtship because you might have seemingly hotter prospects on the hook. One way to keep the enthusiasm is to inject different people into the pursuit and introduce us to them in a choreographed way as we move through each phase of the buying process.

I’ve seen every trick to get us to sign a contract on a supplier’s timeline. The fact is that smart clients will not buy before they are ready. As the curator of the purchase experience, you can get us ready to buy by making sure everyone has the information they need to make an informed decision.

Hope this helps. Happy Selling.

Disclaimer – Donna Donato’s personal opinion does not represent the view of American Express Corp.

Also published on Medium.

Donna Donato

Chris and Donna (Dee) Donato are a husband and wife team who sit at the executive table leading, working, and closing large enterprise deals from both the seller’s (Chris) and buyer’s (Dee) perspective. At home, they sit at the dinner table managing life with three teenagers, a few pets, and an extended global family; from the United States to Russia.

Their deep experience and unique perspectives have led to business altering insights around how business gets done. They are sharing their own experiences at