Three Biggest Tips for Selling Big Deals

The only way you learn how to sell big deals is by selling big deals. – Ryan “The Machine” Majerle

Ryan produced the above quote after hearing Bill Parcels state something similar in reference to winning big games. Our team’s experience selling multimillion-dollar accounts and helping others do the same has shown us that Ryan’s quote is spot on.

Priority1 just finished another Advanced Sales training this month in Houston, TX. This class was made up of tenured reps who’ve been with the company for 9 to 15 months. The content taught at this event was geared toward helping sales reps better identify what a good enterprise opportunity looks like, including the following topics:

– Best practices for booking meetings with owners and C-suites

-Gathering key info for those meetings from other stakeholders in the business

-Uncovering inefficiencies with different departmental processes inside the business

-Presenting and selling on value (not price)

The teaching material delivered to this group came from sales leaders who have proven track records selling to large volume shippers. The reps in attendance were given everything our leadership team knows about how to be successful in this arena. Despite all of that, the quote referenced above will still hold true for each of these reps and for anyone else who dreams of closing big deals one day. No one ever fully understands how to close big deals until they’ve gone through the entire process of prospecting, developing, booking, meeting, closing, activating, and managing a big deal for themselves.

With that being said, anyone reading this article can learn how to sell big deals, but they will also need a good leader who will show, teach, and coach them through each step of the process. See below for my 3 biggest tips for selling big deals that everyone must know.

1. The hardest part of closing a big deal is just getting in the room. Booking a meeting with the “true” decision maker (i.e., owner, president, CEO, CFO, COO, VP, etc.) will always be your greatest challenge. If the person you’re trying to close has manager or even director in his or her title, then most likely that person won’t be the final decision maker. Further, your leader should hold you accountable for booking enterprise-level meetings with the right decision maker. They shouldn’t allow you to book these meetings with shipping managers, directors of supply chain, logistics managers, etc., as it will only set you up for failure. Those people can still be champions for you in the deal, but you shouldn’t try to sell the deal to them. Holding yourself accountable for booking meetings with the true decision maker at a company is the single most important thing you can do to set yourself up for success when learning to close big deals. The first question I always ask when someone comes to me for help on an enterprise opportunity is this: “What’s the name and title of the person you’re meeting with?”

2. The second hardest part of closing a big deal is getting all the data you’ll need to assess the financial impact on the client should they move their business over to you. You can’t close a big deal without getting the buyer to trust you enough to give you their internal financial data. This is an absolute must, and, again, your leader should not let you proceed until this requirement is met. Further, if you’re unable to attain this information from the prospect, they are either not ready to buy or they just don’t want to buy from you.

If you succeed with the first and second parts, you have set yourself up for success, and your chances of closing a big deal have dramatically increased.

3. Finally (my favorite point), you need a leader who will do everything in his or her power to help you land your first big deal if the top two points are met. Furthermore, you need a leader who will help you learn and develop your enterprise selling skillset by showing, teaching, and coaching you through every step of the process. The number one reason people leave a sales job is because they stop learning and developing in their role.  It’s important to find a good leader because no one should ever feel this way at his or her job.  If you think this is the reason why you’re not closing big deals, you should address this issue right away with your executive leadership team. They should be able to give you and your manager the support you both need to continuously grow in your respective roles. It’s important to know that we all need help from others to get better, so don’t ever think that you can’t reach out to any of your leaders (even the higher-ups) for help. It’s their job to help you, so let them do their jobs and let them help you learn to sell big deals even if the leader you report to directly doesn’t have all the answers.

In closing, I want all of you to ask yourselves these questions:

-In the next 12 months, do I want to learn how to sell big deals? If I answer yes, then what is holding me back?

-Lastly, what support do I need from my leadership team to make sure that I don’t fail to hit my goal?

As I said earlier, anyone out there, including all of you reading this article, can learn how to sell big deals, but do you really want to? Are you sure? Really? Just so you know, going through this process will be the hardest thing you’ll ever do, and you’ll most likely fail hundreds, if not thousands of times before you ever see your first win booking a meeting with a true decision maker at the right opportunity.  Even then, success at closing that decision maker and landing that big deal is in no way guaranteed. Now that you know this, are you still 100% positive that you want to put yourself through all of the mental and physical anguish of learning this skillset?

Well… if your answer is still yes, please do this for me right now. Grab your iPhone (it’s probably already in your hand), find your camera app, open it up, click the reverse camera icon, and then just stare at that beautiful image you see on your screen. That strong, smart, super attractive person you see staring back at you is literally the only thing holding you back from turning your dream of selling big deals into a reality.  Does that make sense?  Great!  So whenever you’re ready (take your time), I want you to tell that person on your screen that he or she is not going to hold you back anymore, and let’s go do this thing!


Recent News

Three Biggest Tips for Selling Big Deals

The only way you learn how to sell big deals is by selling big deals. – Ryan “The Machine” Majerle Ryan produced the above quote after hearing Bill Parcels state […]

Read More
Freight Technology: EDI vs. API

Freight Technology: EDI vs. API

Anyone with a software background, or even technology enthusiasts, are familiar with the term API. It’s a pillar of modern web development that has become so commonplace its often overlooked. […]

Read More
LTL Data and Pricing 

LTL Data and Pricing 

LTL Bids and Taxes As we start the new year and we scurry about getting our tax information together, I am reminded of Benjamin Franklin’s famous quote: “In this world, […]

Read More


Priority1 is thrilled to announce Jacob Clanton as our esteemed Employee of the Quarter. Jacob, serving as an Instructional Designer II, has been an integral part of our Learning and […]

Read More

Navigating the Green Highway: A Deep Dive into the US EPA SmartWay Program

In an era where sustainability is at the forefront of global discussions, the transportation industry plays a pivotal role in shaping a greener future. One notable initiative leading the charge […]

Read More

Phillip Scholtes as Chief Technology Officer

FOR IMMEDIATE RELEASE   Priority1 Announces Phillip Scholtes as Chief Technology Officer   Little Rock, AR – December 20th, 2023 – Priority1, a leading innovator in logistics solutions, is proud […]

Read More