What’s Inside the Box of an Enterprise Deal?

By Jennifer Maul
October 17, 2013

Recently, I facilitated a quarterly business review with my sales team. There are many reasons why we do this, but at the core, it’s because something will always go sideways in an enterprise software deal (likely this is true for any type of sales deal). It’s our job as account executives and sales managers to always be thinking about this, making action lists, thinking through “what if” scenarios, and making sure we have our bases covered. Something will go sideways. Guaranteed.

As I communicated with the team on the mission before us as we work to close the year, I was reflecting on a book I am currently reading, Steven Pressfield’s Do The Work!  It is a great little volume about tackling things head on.  Right at the beginning of the book, Pressfield talks about our enemies and our allies in getting things done. I will blog about enemies and how it relates to enterprise sales another time. Today, I want to focus on allies. Our allies in tackling any big thing are: stupidity, stubbornness, blind faith, passion, assistance, and friends & family. I had to laugh out loud when I read the section on blind faith.

“Imagine a box with a lid.  Hold the box in your hand.  Now open it?

What’s inside?

It might be a frog, a silk scarf, a gold coin of Persia.  But here’s the trick: no matter how many times you open the box, there is always something in it.

Ask me my religion.  That’s it.

I believe with unshakeable faith that there will always be something in the box.”

So, a deal is a box. It has a lid. It needs to be opened and closed every day, sometimes multiple times a day. Every time, there will be something in the box. Each time, that thing inside the box is going to be different. Often, it will be a thing that makes you go sideways. If you have crafted your deal strategy correctly and constantly revisit it, handling the sideways surprises gets easier. The following list will help you “do the work” with your deal box and make you a more effective sales person:

1. Develop a strong coach. Who is that one person at your prospect who gets things done, can influence the final decision makers, and will counsel you every step of the way? No coach, no deal. It’s that simple.

2. Decide early if your solution is a fit. If not, get out. You are not doing your prospect or your company any good by pursuing unfit business.

3. Define and constantly message your differentiation platform. It is a platform, just like every good comedian or politician has. And, they do not waiver on the theme. It’s constant. It is rinse, wash, repeat.

4. Plot a people strategy of everyone involved in your deal. Answer one really important question for each of those people – what’s in it for them?

5. Plot a competitive threat strategy. Loop back to point #3. The differentiation platform you pick has to be one that combats your competitor(s). It will likely differ by competitor – be really smart about this and do not take the “let me get out my last PowerPoint” approach. No!

6. Always qualify. Never leave a meeting or call without qualifying, even if you have asked the budget, buying process, vendor preference, project kickoff, etc. questions ten times before. You have a list of at least a dozen qualifying questions – you have to be robotic about it because this is where the sideways surprises start.

7. Agree to a close plan. There is a time in every deal, likely when you have been selected “vendor of choice,” when you have to present the close plan schedule and get agreement. You then have to march to the schedule like any good project manager (account executive) through regular status calls, pristine follow-up, and a constant review of your deal box.

To get started with this list, just ask yourself or your team, are we missing any of these key “do the work” items in managing an enterprise software deal? I wanted to share these because Vendavo is about helping our customers Sell More Profitably. I know from experience that unless you have a process to govern the sideways surprises in your many deal boxes, you will not Sell More Profitably. Instead, you will waste a ton of time and money. Don’t do that. Instead, open your box and learn to deal with your “frog, silk scarf, or gold coin of Persia.”

  • B2B selling , Do The Work! , enterprise deal , Sales Effectiveness , Steven Pressfield

    Jennifer Maul

    Jennifer holds Bachelor of Science degrees, magna cum laude, in Business Management and Management Information Systems from the University of Maryland. Follow her on Twitter: @jmaul_svp