The 2×4 Cheat Sheet For Complex Deals

Founders often have good sales instincts. They can read the room. They can tell a solid story. It’s not always polished or entertaining, but authenticity and passion more than compensate. It works great for one-on-one interactions. Need to convince one person? Recruit one candidate? Court one investor? Most founders are up to the task.

But what happens when a deal is not one-on-one? What if it’s one to many? What if it is highly complex with lines of authority, budget calendars, unclear politics, a procurement department, an RFP process, technology diligence, and/or a legal review? What if multiple people have to sign off to win the deal?

In these scenarios, good sales instincts are important but insufficient. Complex deals are won with process. The kind of process that veteran sales professionals have mastered over years of study, training, and repetition.

You likely don’t have years of sales training. And you don’t have the time to research modern sales philosophies, choose one, and then learn the method in time to impact the deal in front of you.

And at the early stages of your startup’s journey, you can’t yet afford to hire experienced sales leadership. Yet learning via trial and error might cost your company its life.

So what to do?

I present to you Enjoy The Work’s 2 x 4 framework. It’s a super simple structure to organize and move a complex deal forward.

2 x 4 = 2 Dimensions and 4 Archetypes

2 Dimensions: People and Process

  • People — every deal involves a cast of characters who influence decisions, cast votes, sign agreements, raise concerns, and/or passively spectate. Those are the People of the deal.
  • Process — Every business has a methodology by which it makes substantial decisions. That is the Process of the deal.


4 Archetypes

Everyone you meet over the course of a deal can be categorized as 1 of 4 archetypes.

Enjoy The Work Blog post. The 2x4 cheat sheet for complex deals.


The Champion is the person who has come to believe that by buying your product, great things will follow. And those great things directly will benefit her/him. They might receive a bonus. A promotion. See their profile rise. To achieve that fantasy, the Champion will share sensitive information, help navigate the sales process, overcome internal objections, and more. Most importantly the Champion will fight for your deal even when you’re not in the room.


This is the person who signs the check. The larger the company and the bigger the deal, the more likely 1) this person won’t be the same as the Champion and 2) they may be part of a group decision-making body. What this person cares most about is not the Champion’s fantasy, but the cold rational math of the deal.


Have you worked with procurement before? How about IT? Or perhaps security or compliance departments? Let’s imagine you’re selling marketing software. You find your Champion in the Director of Content Marketing. She loves it, understands the potential, walks through multiple demos, checks references, and negotiates a deal. She crafts a story and an economic justification for the CMO (aka the Buyer). But just prior to finishing the contract, she shares with you, “We just need to do a brief technology review to ensure security compatibility…” Welcome to the Blocker. This is the person who can say “no,” but not “yes.”


Large deals tend to happen with large companies, and large companies employ a lot of people… Throughout the process, you will meet some people favorable to the transaction, but only as spectators. They’re watching the contest play out in front of them. They might even have a rooting interest in what the founder is attempting to sell; but, they will extend only limited help (if any at all). They smile and wave from afar, taking no political, reputational, or budget risk of any kind.

* In fairness, there is a 5th category of person, someone irrelevant to the deal who has no influence and neither cares positively or negatively.


Every B2B startup has a sales motion of some kind. You very likely perform some type of qualification, deliver a product demo, evaluate the lead’s needs, offer a proposal, perhaps execute an initial pilot, and then ideally negotiate an agreement.

We encourage founders at even the earliest stages to be thoughtful about their sales playbook. Write it down. Document your ideal customer profile, the hypothetical sales stages, the pitch, and the anticipated objections.

But in large complex deals, the Process about which I also want the founder to obsess is the one the customer employs.

Many enterprise startups have crashed on rocky shores after too long trying to wrangle a large enterprise buyer into the founder’s young sales motion. Legacy companies both have hardened processes coupled with a myriad of more subtle rituals that together determine whether a substantial contract with a third party can be executed. The founder’s role (if not their obsession) is to learn both the process and the rituals.

To do that requires a set of questions and vigilance. Your Champion is your best bet to understand the gauntlet your deal must traverse. However, almost every person with whom you interact might offer a useful nugget. And the more people you can meet the better. The key is to know what questions to ask.

What to ask to uncover The Process

  1. Does your company have experience buying <insert category of your business>?
  2. Is there a committee or a group particularly responsible for approving <insert category of your business>?
  3. If yes, when is the next time that group meets and how often do those sessions occur?
  4. (for the Champion) What information do you need to help that group reach a decision?
  5. Who are all the people or departments typically involved in making this type of decision?
  6. Is there a budget line item already in place for <insert category of your business>?
  7. When does your legal department get involved? How long is the typical process to go from us having alignment on business terms to getting a contract in place?
  8. Do you have a standard contracting approach, MSA + SOW for example, for <insert category of your business>?
  9. What helps deals go through this process smoothly?
  10. When something slows down or hinders the process, what are the most typical reasons?


And here’s the painful rub. You’re likely to receive conflicting and/or confusing answers to many of these questions. Why? Because as a startup founder you’ve developed a new toy with which this big legacy company predictably has no experience. They’ll try and wedge you into their Process but they might have to improvise a bit to get approval. And improvisation for big companies is not easy.

That’s why you’re not going to just ask the above questions once; but in fact, you’re going to ask them constantly and to everyone until you see enough consistency in their answers to know that you’re progressing through the maze.

Enterprise selling is hard. It’s even more difficult when you’re an inexperienced founder with a young product trying to convince a big company to take an expensive risk. The siren call of one deal forever changing the trajectory of your company is often too hard to resist. We’re not telling you to run from opportunity, but rather to look where you’re headed so that you don’t accidentally get hit in the head by a two by four. 🙂

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