Time and time again, I see situations where an enterprise sales rep is in the late stages of a deal, they’re two to three weeks out from end of quarter, and all of a sudden a deal that’s already been committed starts going south. The prospect starts questioning things, is unsure of the timeline, or maybe just flat-out started going silent. This is bad.

When situations like this occur, and the rep can’t leverage his or her relationships to drive the deal forward, that’s when it’s time to go up in the food chain. Maybe a note from rep’s VP will compel them to say what’s going on. But, the VP hasn’t been introduced to the account yet, which means that without credibility already established he’s going to be viewed as just another sales resource from the vendor trying to save a deal. The response rate and effectiveness of this approach is very low.

Now, had the rep introduced his VP into the sales cycle much earlier on, and maybe had established a meaningful relationship between the VP and other executives in the prospect’s account (executive alignment), those could then be leveraged in the emergency situation.


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If you wait until you have a fire on your hands to align executives, it’s too late. You’re toast.

Why Do I Need Executive Alignment?

Executive alignment is essential as a point of escalation in a deal. When you’re in the weeds of the deal with your day-to-day evaluators, they may not have insight into other departments/divisions or into processes that are outside of their purview. Sometimes they have no clue where things are in procurement, or are unsure where a signature stands, or are taking a hard stance on something that’s crucial and you’re getting nowhere. That’s when you can hopefully write one of your executives and say, “Remember that VP I put you on the phone with a couple of months back? Would you mind sending a note to him to see if you guys can have a quick chat about….”

Executives have very little free time, tell you how it is (straight to the point), and can leverage their internal pull to make things happen faster when you need it. It’s just a totally different level of conversation.

Be careful though. Overusing this dilutes the value of the alignment, so use this only when you absolutely have to.

Which Executives Should I Align?

Whenever possible, try to align titles or functional responsibilities. If I know that my prospect’s CMO is questioning things or showing signs that she’s not fully a supporter, I’ll try to align my CMO, or any other C-level executive if my CMO is unavailable or I don’t have one. If the person you’re dealing with is at a VP level, from the business side, your VP of sales will do just fine. However, if that VP is technical, your VP of sales will likely not work. You’ll want to align him or her with a technical leader from your side.

In summary, if you strive to match seniority, function, and personality to the best of your ability, you’ll be in good shape.

When Should I Introduce My Executives Into the Sales Cycle?

As early into the sales cycle as possible. You never want your prospect thinking that you’re introducing someone just because you’re in a bind. You want to make those introductions and start building those relationships while everyone is still in their honeymoon phase with each other. The more connections you make, the more durable your deal becomes, which will help you weather the storm when the evaluation gets hairy or competitive later in the cycle.

How Should I Position My Request for Executive Alignment?

There’s internal positioning and external positioning. Once you’ve identified where executive alignment is needed, you need to properly brief your executive and ideally craft a ghost-written email that he or she can send off to establish the introduction. Let’s say I’m trying to align my CEO, here’s an email I would send to my CEO.

To: My CEO

CC: My Manager

Subject: Executive Alignment Request


Background: I’ve got a $300k opportunity with Coca-Cola on the table, with a close date of 3/30. We’re about to go into the demonstration phase, but I’m sensing some hesitation from their COO. You both worked at SAP together from 2014-2016. He came from a shop that was using a competitive product and will participate in next week’s demonstration.

Request: May you please send the below email? My goal is to establish a relationship between the two of you so we can begin turning him into a supporter of ours. He’s clearly hesitant, but isn’t being forthcoming about his concerns, so if you can attempt to uncover those during your conversations, that would be meaningful.

To: Mr. COO (mrcoo@coca-cola.comm)

Subject: Steve/Mr. COO Introduction


Mr. COO,

My name is John Doe and I’m the CEO of ABC Software company. It looks like we both worked at SAP together a few years back. I still stay in touch with some of my old team over there. Their M&A activity has been through the roof recently, so It’s been interesting to watch.

(Note about above. Don’t make it all about THIS deal. Insert something personal.)

Anyway, I understand that our respective teams are beginning to engage around your evaluation of our platform. As such, I thought I’d reach out to introduce myself and to offer up my time and support as you evaluate your options.

May we schedule 30 minutes sometime over the next couple of weeks so I can get to know you a bit better? I’m also happy to answer any questions you may have about the direction we’re taking the company and our vision for the future.

Just let me know your availability and I’ll make sure we get something locked in on the calendar. In the meantime, if there’s anything I can be doing to add value please don’t hesitate reaching out. My contact information is below, including my cell.

I look forward to chatting soon.

Warmest Regards,



Assuming this relationship gets established successfully, you should indicate this, visually, in your Buyer Map. That way, as you look at your deal from a 30,000 ft. view, you can visualize where you had gaps and how you filled them with executive alignment. At the end of this exercise, hopefully you’ve got a buyer map filled with supporters and lots of established relationships (multi-threaded).


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