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My strategic accounts sales team met me in our NY office for a final briefing before our big meeting. After my usual grilling questions, I packed up my laptop and some choice tools for the job.

I loaded a pair of red Vic Firth Drumsticks in my briefcase and taped up a box of a dozen bright orange “Made to Stick” books written by the Heath Brothers. These were the props for what my sales team lovingly called, “The Belizaire Show.” When they brought me, the CEO, into a meeting, it was game on.

The Belizaire Show” usually included just the right mix of strategic vision, audience participation, storytelling, product demo, and finally, the magic moment.

Nancy Duarte, best-selling author of Slide:ology and Resonate, likes to call it a STAR moment, Something They Always Remember.

We presented to a room full of senior executives during their strategic offsite. There were several vendors slated to deliver pitches including some direct competitors. It was our chance to shine.

We delivered a stellar presentation about transformation, including rich customer case studies and an eye-popping demo.

We did not stop there.

At the close of the presentation, I did something unexpected. I opened my briefcase and pulled out my set of drumsticks.

I asked for a little more time and indulgence from the audience. The host was reluctant to give it but intrigued enough to say yes.

I paired up two of the senior executives in the room. I gave one of them the drumsticks and asked him to tap a tune I had written on a card. (It was the happy birthday song.) The second person’s job was to guess the song.

After a few attempts, the participant assigned with guessing failed to “name that tune.” I then stopped the exercise and explained the point.

“To truly transform your company, you must think differently. Otherwise, you’ll miss the music,” I said.

I then opened the box (quietly sitting in the corner of the room) and handed each person a copy of the bright orange books. I explained how a chapter in the book was the inspiration for the exercise.

That Magic Moment helped open the door to this account wide open, winning us a multi-million-dollar deal, one of the largest in our company’s history.


There is a lot of content out there focused on B2B SaaS sales strategies for companies primarily selling to SMB markets.

Large account enterprise selling is different. It is an art.

Enterprise selling is all about finding pain, connecting with people and delivering magic moments.

The number one salesperson in any company is the CEO. If you are the CEO, you need to understand this crucial principle, among others.

In this series of blogs, I will share some of my experience and lessons. Topics will include getting in, building relationships, selling, building sales teams, and differentiating your company.

Today, we’ll start with the basic framework.


1. FIND PAIN
I can not overemphasize how important it is to find pain.

Connecting a solution that solves a specific, significant pain is the key to enterprise sales.

In my first company, TheoryCenter, we focused on helping Fortune 500 companies build e-commerce applications faster. We provided our customers with “lego blocks” for 75% of the most common application components they had to create for new Internet-focused applications.

It was a real challenge for traditional brick and mortar companies and new dot-coms alike. They needed to get to the web fast, and our solution provided a turbo boost.

At FirstBest, my second venture, we helped companies transform their underwriting operations to drive scale and “entirely better” underwriting. Their distress was born from their highly manual processes and lack of data in the decision process. (A summary of the process we used to find the pain is here.)

How do you know you have found pain?

Well, for one, the customer should be looking for aspirin, not a vitamin.

In other words, the pain should be so acute that they must have a solution today or continue to endure this aggravating discomfort. Products that address a real pain, with rapid ROI, are bought, not sold.

Ideally, you find pain before you even write a single line of code. When you do, stop at nothing to deliver a dazzling solution 10x better than anything else.


2. START WITH VITO
VITO refers to the Very Important Top Officer. They could be a CEO, CIO, CRO, CFO, SVP of a business unit. Usually, the most senior person in a target company that viscerally connects with the pain you solve is the VITO.

I often say to entrepreneurs, “if you are not talking to a VITO, then shut up and start looking for one.”

VITOs are also the folks who are either the budget owners or release the budget to other parties. They ultimately become your champion and lead you through the rest of the organization.

They help to form selection and decision committees, and they are the primary advocate on your behalf.

In my second company, our VITO was the Chief Underwriting Officer. This person felt the pain every day as they got out of bed.

In my first venture, the top officer was the CIO or business unit head, responsible for delivering a rapid transition to the web.
Developing a relationship with these senior folks is key to the success of any enterprise software company, hands down.

If you end up working with a broader group of folks at different levels of the organization, it’s OK. But, always start with the VITO.


3. GIVE THEM A MAGIC MOMENT
The magic moment I described earlier might seem like a bit of showmanship. It might even seem a bit gimmicky.

Trust me. It is not.

What if I told you that I had done this consistently using a variety of personalized “moments” for each audience opportunity with nearly 98% success in advancing the relationship?

(I have done it for every audience from customers, to venture capitalists, to conference audiences, and even to employees.)

The magic moments allowed my companies to stand out in a sea of vendors when it counted.

VITOs see pitches every single day. They are hunting for the one company that can make a connection that leaves a lasting feeling in their gut. They need a good story they can get behind.


According to Yuval Noah Harari, author of Sapiens: A Brief History of Human Kind, we are all predisposed to need stories. “The wandering bands of storytelling Sapiens were the most important and most destructive force the animal kingdom had ever produced,” he explains. “How did homo sapiens manage to cross this critical threshold, eventually founding cities comprising tens of thousands of inhabitants and empires ruling hundreds of millions? The secret was probably the appearance of fiction. Large numbers of strangers can cooperate successfully by believing in common myths.”


As Nancy Duarte puts it, “a [STAR] moment should be a significant, sincere and enlightened time during a presentation that magnifies your big idea — not distract from it.”

I believe this technique works for me because I am always sincere. I take the time to understand my audience through direct and indirect research.

I study what makes the audience tick, their wiring, what keeps them up at night. I hunt for their resonance frequency and what exactly I need to do to make my message stick.

By the way, magic moments can be anything from a memorable dramatization (like my drums sticks shtick) to repeatable sound bites (like “I have a dream…”). It could be incredible visuals (like a charity:water video), case studies delivered through rich storytelling, and data or statistics that blow them away.

Remember, your customers, prospects, and employees are people.

People are excited by making a real connection and are wired to crave experiences that move them. Give them a magic moment.

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4. BUILD THE RIGHT TEAM
Sales teams are the lifeblood of any growing enterprise software company. A sales team’s DNA determines its success.

In fact, I believe the best way to elevate your venture is to think about its DNA from the very beginning and hire as if your life depended on it.

Some of the best enterprise salespeople I have ever met worked for BEA Systems, the company that acquired my first venture. They were patient, aggressive, and process-oriented all at the same time. And, these sales professionals worked as a team like no other.

These folks were sales machines. They could enter a building cold and convince everyone they should stop breathing oxygen and breath nitrogen. They were long-term thinkers and strategists that always set the stage for a multi-million-dollar sale.

Hiring the right sales leader and team is like putting the proper fuel in your car. If you want it to perform at the highest level, you must load it with the right octane. Make sure you have the right “sales boss” and the right team members.


Here are some things to keep in mind when building a sales team:
(1) Hire athletes — Literally. The best sales bosses have been superior athletes in college and are driven to win. They’ve been trained to value teams and work as a member of a team. Most importantly, they have been trained to practice and perfect their craft.

(2) Consider a counter-intuitive approach — If you are a vertically focused company, in FinTech or InsurTech, for example, you might feel compelled to hire a sales team from the sector. This approach could seem sound, but it could also be misguided.

In our insurance-software company, we learned the best model for a winning team was to combine sales athletes (with limited or no domain knowledge) with deep subject matter experts.

This two-in-a-box approach was counter-intuitive and costlier. But, it worked much better. Before you start hunting for former “bag carriers” from legacy companies in your chosen market, consider a different approach.

Hire sales athletes, teach them the domain, and then hire users (people who connect to your pain) to be your subject matter experts and pair these two together.

(3) Specialize — People who love to open doors are not the same as people who prefer walking around the house once the front door is open. Hunters are different than farmers. I am sure you’ve heard this concept before. It turns out this idea is valid for every role on the sales team, inside sales, BDRs, sales support, account executives. Make sure you hire people who are experienced and specialized.

(4) Check their wiring — We are all wired differently. Sales people especially are “coded” with certain traits including competitiveness, independence, urgency, process-orientation, communication, self-confidence, and more.

When building a team, check the wiring of each person and make sure they match the roles you are putting them in. There are many tools out there to help with behavioral diagnostics, and most of them are good — you just have to choose one. One of my CEO friends swears by the Predictive Index.

(5) Match their experience to your stage — Don’t hire a sales leader who just ran a $500M business at a large global company if you are in the early stages of your venture.

(They wouldn’t likely come work for your company anyway, but I use this example to make a point.)

You want to hire a sales team that matches the stage of your company. Ideally, they have just completed the same phase of growth you are about to enter. While this means you’ll likely outgrow them later, you won’t be frustrated by someone who no longer wants to drive growth at a lower level.


5. BUILD A PLAYBOOK
Whatever you do, don’t hire a sales team until you have sold your product at least five times.

Why? Sales teams are skilled at taking a successful sales approach and scaling it. Plain and simple. If you don’t know how to sell your product, no one else will.

Why? You are the best salesman or saleswoman.

I recommend to new founder-CEOs that they learn the art of selling themselves.

If you don’t have the wiring to do it, then find someone, a single person, and make them your business development partner. This person is a “lone wolf” whose job is to balance your weakness in sales and help you get deals to closure.

Once you’ve sold your product several times and it does not feel like a herculean effort every time, you are ready for a playbook.

A playbook answers a simple question: “How the heck does someone sell this thing?”

Questions like: who your target customer is, who is the user, what pain do you solve, how do you price, how do you get in, how you do compete. The playbook also answers questions like: how do you conduct an evaluation or pilot, and what are the most common objections.

There are some decent firms out there that will help you develop your sales playbooks. Most importantly, you need to have one. Then you must develop a boot-camp style training course to ensure your teams master it.


Stay tuned for part two of this series, where I will share more lessons including compensation, using your network, when to show up, the importance of looking bigger than reality, and more.


#CEO Podcast: You’re a CEO, But Don’t Think You Need Sales Skills Huh? (with Jim Hemmer)