So you are looking to move up-market? There are some things that you and your team need to know before you start closing those $100k+ deals.

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Bigger deals are more complex, involve more people from the customer’s side and from your side, they take longer to close, and they require a more sophisticated sales approach. But the juice is worth the squeeze when you can get a customer who pays you $100k+ each year for your product or service.

Enterprise customers are more valuable than just the revenue. These customers don’t churn because the switching costs are so high to move to a new provider. Once you have them, you will have them for 3+ years.

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These customers also have a recognizable brand which makes your company “safe” in the eyes of other enterprise customers. “Safe” means more referrals, more organic inbound, and more top of funnel for your enterprise sellers.

There are many reasons why moving up-market can be the right move for your company, but you must be sure that you are aligning your go-to-market motion and your selling motion with this type of buyer.

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For most companies, if you can close a $100k deal then you can close a $500k deal. There isn’t that much of a difference in the sales cycle or selling motion.

Where people get stuck is when they close enterprise-level logos in the $20k - $50k range. They are planning to “land and expand” into these accounts, but the expand part never comes.

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Deals that hover around $20k - $50k  are usually single-threaded (read: only 1 or 2 buyers) and don’t have enough internal buy in to grow to $100k+. This happens when your salespeople  really haven’t had to navigate a sale with more than 2 or 3 people evaluating the deal.

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Here’s how you coach them through these big deals…

Four Stakeholders to Look for in Every Enterprise Deal

In every enterprise deal, there are four stakeholders that you need to be aware of:

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The Champion

This is your main point of contact on the deal. They are the one who cares the most about buying the product or service. They are coaching you on how to navigate the buying process in the organization. They are going to the internal meetings (that you aren’t allowed to be in) and advocating on behalf of the product or service. They will fight through internal resistance and detractors to get your deal done.

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Remember that Champions are putting their career and reputation at risk by pursuing this initiative. Take care of your champions and they will take care of you. It’s your job to make them look good so that they get recognized, rewarded, promoted, etc. If you don’t have a Champion, you don’t have a deal.

There’s a lot to be written about finding and working with Champions, I’ll save that for another post.

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The Technical Buyer

If you are selling software, this is usually someone from IT who is responsible for implementing the technology. It doesn’t always have to be IT, in some cases the technical buyer is in an operating role but possesses knowledge about how to put the product or services in the hands of the team so that the company can start to get value from it.

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Technical Buyers can be a HUGE asset in the selling process if you help make their job easier. I have never met a Technical person at any company who has free time. They are overwhelmed with tasks coming from all different directions. Maybe they are evaluating a new ERP for the company, or they are going through a system-wide security upgrade. By the time you are introduced to the technical buyer, they are probably trying to figure out how to block the deal or hand it off so they don’t have yet another project on their plate.

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So how do you win over Technical Buyers who are too busy and overwhelmed to take on your product implementation? The key is to help them understand that implementing your product is going to be simple because they have a great partner. This requires your product team to have great APIs and documentation for the customer. This requires that your own implementation team is present, responsive, and helpful. If you have this support, even if you have to do some of the work yourself, you can feel confident that you will be a good partner for your customer.

Technical Buyers love to understand how the product will be implemented and how they can move on to the next project on their crowded plate. That’s it. So keep the conversation simple when you are engaging with the technical stakeholder.

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The Economic Buyer

We all know this stakeholder. Mr. Moneybags. The one that signs the check. It is usually an executive or senior leader that has purchasing authority for the business. It may even be a C-level executive if the project is big enough.

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The economic buyer is usually involved once you have confirmed that the product will deliver value and the product can be implemented. You will not be able to close a deal without the economic buyer signing off.

The challenge with this stakeholder is that they are spread thin across so many initiatives, they are not likely to see your product as their highest priority. That’s where you need to get to work.

I like to use two different methods for engaging the economic buyer.
1. Get them in a meeting - If you can get them in a meeting, you will have the best chance to influence their decision. Face to face is always best. You can learn more about their key priorities for the year and understand how your product fits into their plan.

2. Build an Executive Summary - Whether or not you can get the executive in a meeting, you must build an executive summary of the partnership. This is a 1-2 page document that outlines why this partnership makes sense. It includes the following:

• The status quo and why this is a problem for your customer
• The desired outcome of a partnership
• A summary of the products or services that will address the customers’ problem and deliver the desired outcome for their business.
• Key stakeholders (names and titles) of everyone involved on both sides of the partnership
• Timeline for implementation and a roadmap to success
• Summary of the cost and economics of the deal.

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Economic buyers are busy, they are executives, they don’t want to get into the weeds, but they are also human. So be human with them when you are selling. Understand what will make them look good to their peers in the company. Take the risk away from making the purchase and partnership with your company. That’s how you win over Economic buyers.

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The Legal Buyer

Every enterprise deal requires legal approval. I have seen so many deals blow-up because the seller doesn’t approach the legal team as a partner in the process. The legal team is not evil. Their job is to protect the company from risk, and you are the risk.

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Legal needs to make sure that partnering with your company is not going to expose them to outside loss or liability. Assuming you are not doing anything nefarious with your customers and their data, the real conversation with Legal is helping them understand what your business does and how you will be interacting with your customers (and your customers’ customers).

I always recommend talking with Legal before you send over your contract for review. By this time, you should have already negotiated with your Champion and Economic Buyer to get the right price. The only thing left is to make sure the terms of service comply with your customers’ policies.

Legal cares about indemnity, limiting exposure to financial commitments and financial risk, and in most cases Legal cares about looking useful.  Like death and taxes, legal will always redline a contract. Even if they agree with everything that’s written, lawyers are conditioned to put things in their own words to show that they are providing value to the company. There’s nothing wrong with this, just know that it is part of the relationship you have with the Legal Buyer.

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How to Navigate Dysfunctional Buying Groups

Any time you are selling to a group of two people or more, you are dealing with a dysfunctional buying group. By nature, humans are imperfect at sharing information with each other. If you need any evidence, look no further than the relationship you have with your significant other. The last time you bought anything of value - a mattress, a couch, a car, a house - there are so many emotions, intentions, and observations that are not communicated in the process of making a purchase.

If it’s difficult to communicate with someone you share a bed with, imagine how difficult it is to communicate with the person who signs your paycheck? Or a person you are competitive with at an executive level.

In a business, there are so many hidden agendas, politics, emotions, and priorities that influence how a deal gets evaluated. None of these factors have anything to do with your product or service, but they influence how the buying group makes a purchasing decision.

It’s your job as a salesperson to help the customer navigate these internal headwinds so they can purchase and successfully implement the product or service. To be the best partner to your customer, you have to understand the dynamics of the buying group and get all stakeholders on board.

The Buyer Circle

Every buyer goes through a process in evaluating a product. Neil Rackham, the guy who wrote SPIN Selling, does a great job of illustrating the process that buyers go through when evaluating a product.

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The above image comes from one of Neil Rackham’s other books Major Account Sales Strategy. Most buyer’s being their evaluation at the very top of the circle in a stage I like to call “Business as Usual”. You have heard this before when you reach out to a prospective customer and they turn you down because they are happy with their current solution. As the business grows or the market changes and the buyer experiences some pain or challenge, they will move into a stage called “Recognition of Needs”. In this stage, the buyer is painfully aware that they need to change something about their status quo. From there, the buyer will “evaluate options” available in the market that address the current challenges in the business. They will “resolve concerns” about the available options and narrow down to one or two final solutions. Then they will “decide” which solution to implement by purchasing the solution and they will move forward with implementation. Once the solution has been implemented, there is a new “business as usual” for the customer and they are right back at the top of the buyer circle.

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This may seem simple enough when considering one buyer, but what about when there are 4 buyers involved in the sales?

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That’s what makes enterprise selling so complex, you need to get the entire buying group through all the stages of the Buyer Circle to get the deal over the line. There are no shortcuts, unless you have an executive unilaterally make the purchasing decision. And even in that case, there are challenges with implementation because the other stakeholders were not bought in.

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Take the time to understand how teams make purchasing decisions. This will help you build consensus in the deal and accelerate the time to a decision.

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Pulling it all together: Joint Execution Plan

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Never assume that customers know how to buy things. In most cases, the customer that you are selling to buys a product once or twice a year at most. This isn’t like going to the grocery store for milk. This is enterprise sales, you are asking them to spend $100k or more. This is probably more than your Champion makes in a year. The contract might be worth more than your Champion spent on their home.

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Put this all in perspective when you are working with your customer. They are operating without a ton of experience buying high-ticket items. They are unsure if the product is going to do what you say it’s going to do. They are scared to put their career on the line to buy this product.

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They don’t really understand how to get the product bought in the first place. Who needs to be involved? What are the steps in the process? Do we have the budget?

This is where you come in as the experienced salesperson. You are there to coach them through buying your product or service. You are the steady-hand to help them solve the problems in the business.

The best way to align with your buyer and help them navigate their own buying process: Joint Execution Plan (JEP).

The JEP is a great resource to show your customer exactly the steps to get through purchasing and successfully implementing the product.

The jep is a simple chart that shows the date, the action item and the owner for each stage of the sale. A simple JEP would look like this:

- 9/15 - Demo with CFO, Director, and IT - John

- 9/20 - Meeting to review pricing with CFO and Champion - Angela
- 9/25 - Meeting to review legal - Angela
- 9/30 - Finalize redlines and execute contract - CFO

- 10/3 - Kickoff call - all stakeholders

- 10/6 - Review API implementation - IT, John

- 10/10 - End-User Training #1 - Angela, John

- 10/11 - End-User Training #2 - Angela, John

- 10/12 - Go-Live - all stakeholders

- 10/15 - Go-Live review - Angela, John

- 11/15 - 30 day implementation review - Angela, John, CFO

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This doesn’t need to be formal. It can be in an email. It will evolve as the deal evolves. The most important thing is to build this JEP with your customer. When you create it together, they are more bought into the plan to purchase and implement the product.

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When you couple the JEP with the Executive Summary, you give your deal the best chance to move quickly toward a “yes”.

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Bring the Mini-Van and Beware of Hidden Hillarys

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Enterprise sales is a team-sport. There are no bonus points for going it alone. You don’t get paid more. The company doesn’t make more money. There’s really no benefit to shouldering all of the burden yourself.

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And plus… winning as a team feels SO much better. When you are working an enterprise deal, you want to include as many stakeholders from your side as are involved on the customer side. Maybe even a few more from your side compared to the customer.

If you have 4 stakeholders on the customer side, match it with 4-6 stakeholders from your side. This shows the customer that there is an entire team committed to making the project successful. This also gives your team an opportunity to learn about the customer and how you can deliver success for their business. Your team will notice things that you don’t, they may even find ways to expand the deal that you can’t even see.

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Like a soccer-dad dropping the kids off at soccer practice, enterprise sellers need to put the team in the mini-van and bring them into the deal.

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And finally, every enterprise deal has hidden stakeholders that influence the deal. We call this stakeholder Hidden Hillary. She is a phantom character because she exists but you will never meet her. It could be an executive that isn’t involved in the deal but is influencing the buying group. It could be one of the Champion’s peers who is jockeying for position in the company and doesn’t want your Champion to succeed.

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Just know that Hillary is out their and she does not want your deal to go through. Sometimes you can ask your Champion outright “who does not want this partnership to happen?” But your Champion may not even know who Hillary is. So stay vigilant. Work with the stakeholders you know and help them navigate the purchase decision. After all, that’s your job as salesperson.