June 6, 2017

Enlist “Spies” to Help You Win More B2B deals.

It’s the information you have, that your competition doesn’t have, that helps you design the winning strategy.



This article addresses the need for your sales people to understand strategy and tactics at the account level. You can’t plan for everything, but you can keep your eyes open for factors that will impact your win/loss rates. 

Companies who sell complex solutions to businesses often find themselves immersed in lengthy sales cycles, spanning several months if not years. Deals are competitive and a drain on your resources. The stakes are high to win the deals you decide to play in. 

The truth is, there are times when factors outside of your control will impact your ability to win a deal.

Often times, if your sales teams are paying attention, these factors can be identified, and as a result, contribute to the design of your account level strategic and tactical plan.

One way to ensure that you are always on top of these “red flag” type factors, is to enlist the support of a team of “spies.”

What do I mean by “spies”?

Complex sales cycles demand that you gather information that informs your actions.

Sure, much of the information you gather will come directly from your prospect. Could be that you have a trusted source of information within the walls of your buyer, though that is not always the case. 

My advice is to develop trusted sources of information that exist outside the walls of your buyers. These are, in my view, people who function as “spies” that inform your account strategy.

These are people who can tell you what’s going on at the company you are trying to sell to, and inform every move you make to win the deal, even when it appears to everyone else that there is no chance in hell you are going to win.

True Story

Years ago I worked for a company called Peoplesoft. I got a lead for a company that showed a lot of promise. It was a consulting firm near Boston, MA, specializing in providing services to the government. I met with the CIO almost 2 years before the deal finally closed. 

The CIO was a nice enough man. However, he had just hired a project manager to take the lead on the initiative that would fund my sale. The problem was, the new project manager came from my number one competitor at the time, Oracle.

This new project manager gave me every indication that his bias was going to creep into my commission. 

I confronted the CIO to see if this project leads bias was going to creep. Naturally, I was assured it would not, and that all vendors would be given a fair chance of winning the business.

Little did the CIO and his new, heavily biased project manager, know how wrong he was.

The Call from an Unknown

In this particular deal, I got a call from a VP of Sales from a consulting firm in Virginia. I had never heard of the person or the firm, but took the call just the same. My habit was to never turn away what could amount to a valuable resource of information, a spy if you will.

Thank god this was my m.o.

Best Man

Turns out, the CEO of my prospect was the best man at the wedding of the CEO of this firm in Virginia. Or it was the other way around. I can’t recall. What I know is that one way or another, one of them was a best man at the others wedding.

They were so close, that the CEO of my prospect shared with the CEO of the firm from Virginia, that in no way shape or form was his company going to select Oracle. He in fact hated Oracle.

No one but the two CEO’s, the VP of Sales and me as a result of taking the call from the VP, knew what the situation was. Not even the CIO and his extremely biased project lead.

In fact the CEO at the prospect, as part of letting his people do their job, was willing to let his team, CIO included, do their due diligence. If they chose Peoplesoft, good. If they chose Oracle, bad.

Street Fight

Oracle and Peoplesoft were like Brazil and Argentina back before Oracle bought Peoplesoft. In other words, we hated each other. At least I hated Oracle. 😉

I viewed any competitive situation with Oracle as a street fight, because they were down and dirty, nasty and ugly battles.

This deal was no different.

We went at it for over a year, and as I suspected in the beginning, the project lead had a massive bias for the Oracle bus. 

The Oracle Bus was the term we used to define the army of Oracle people they would throw at a deal to suffocate the prospect, and keep the competition away.

Anyway, the bus was in full effect.

In the end, Oracle won the deal…or so they thought, because they executed the deal flawlessly. 

“You can’t win, you just got kicked off the account.”

I was not favored by the CIO or his biased minions. In fact, I was hated. They wanted nothing to do with me, and told me so, and told my boss so. According to them, I was the worlds worst sales rep. One could say that I was outdone by a rep at Oracle who seemed to execute better than I did.

The CIO called my boss at the time and just about informed him that they had a restraining order on me. In my bosses mind, I lost. He was adamant that there was no way I was going to win the business.

He was wrong.

The contract was signed in our favor about a month after I was kicked out.

“How did you win that deal?”

I insisted that my boss negotiate the contract in my absence. He thought I was crazy, mainly because I still had not revealed why I knew I was going to win. I couldn’t. I was sort of sworn to secrecy.

None the less, the contract came our way, and in the end, my boss, the CIO and Mr Bias Creep had no idea what had just happened.

The best part of it for me was when the Oracle Rep called me on the phone, in shock and awe, asking me how the hell I won that deal? He was desperate to learn what had just happened to him, mainly because the the CIO told him to forecast the deal for the Oracle win. In other words, it appeared from just about every angle that he executed a flawless transaction.

I told him simply not to take it too hard. He could not have known what had happened, and really did nothing wrong. Oracle as a company did, long before this deal ever went down. They messed with the wrong CEO and the CEO messed back.

No way a rep could have known.

Develop Your Sales “Team”

I always viewed people, inside and outside of my company, as a partner, collaborator or at a minimum, a source of information.

This wasn’t something I was taught in sales training. It was just something that made a lot of sense to me. So, anyone who picked up the phone to call me about participating in my world was a potential source of help and assistance in bringing a deal to close.

I never ignored people, no matter if I knew who they were or not, because anyone who wasn’t me, was a potential “spy” that I could recruit to help me plan the account strategy that gave me the best chance of winning.


I don’t know about you, but value propositions alone were rarely enough to get a deal over the line.

In B2B sales, where there were a lot of people involved, and a lot of time to consider things before making decisions, much rested on knowing little bits of information that revealed what one person or another was thinking.

It was in those little bits of information that I often found the vision for the winning strategy. In this case, the winning strategy was to shut up, show up, take the beating and collect the check. I laughed all the way to the bank.

And before you go on and assume this was an anomaly, I’ve got at least a dozen stories just like this one, though not as profound, that reveal that recruiting “spies” is a great tactic. 

Think of it this way. The beaches of Normandy were not stormed prior to an attempt being made to locate the German Defenses. Losses were still high, but try to imagine the losses if no attempt was made to gather intel.

See my point?

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