So you’re tired of transactional selling, it’s burning you out and you are not hitting your financial goals. You want to move into the enterprise segment - fast. 

Here’s how you do it:

There are typically three ways the transition happens:

1. Your current company decides to go upmarket for the first time and assigns you ‘enterprise accounts’ whatever that means in your context. Typically they give you no upskilling or new tools. It’s sink or swim.

2. Your current company has an enterprise team already and you kill it as a mid market rep, have a story of doing an uncommonly large or complex deal and you get an internal promotion.

3. You get a new role at a new company and they think you have what it takes to sell to the enterprise.

Let’s focus on what you can control today to start behaving like an enterprise seller. Right now. In one of your accounts.

1. Plan out your strategy up front

Slow down and think through your approach to a potential deal. Navigating a larger account or a larger deal will have levels of complexity that you aren’t used to. If you want to catch a fish you can take your fishing pole and some bait, walk to the pier and cast away. If you want to hunt a whale, you’ll need months of planning, a whole village of kayakers and a bunch of gear.

2. Deep research-enabled customer-specific messaging

Don’t use pre-made email sequences. Before you send the first outbound message, research the account much more deeply than you do for mid-market accounts. Customer specific messaging is the only way to break through the noise of 400 emails coming in daily to a decision-maker’s inbox. 

Here’s the switch from bad to good messaging:

Bad: “Do you suffer from credit card fraud? I have just the thing for you,” to: 

Good: “As (account name) addresses G-WEN fraud detection in its ‘One-Touch’ checkout campaign, below are three areas we can support its CIAT and CIAF processes…”

Referencing your account’s current pains and ambitions using their nomenclature will set you apart from the tens of thousands of reps who just don’t do the work to get smart.

3. Involve your executives and give them a specific role

Many mid-market or commercial reps don’t involve any of their management team in their deals except their first line sales manager. When you have a coherent plan, include a relevant executive in it, give them a specific role and let them see how you operate, magic can happen.

At the beginning of a new fiscal year I once had a new manager and a new VP of Sales. They didn’t know me. I briefed my manager on a small deal I was working on and invited him to a working session. His only role was to listen and give me feedback. I had a detailed agenda and was super prepared. After the session we debriefed and my manager was floored. “Jamal, I’ve only sold apps my whole career but the session you led went way into their tech architecture and infrastructure. I’m amazed at how you used that as support for using our app as the best fit for their applications landscape!”

A month later I was given the global account that became my first mega deal. When my new VP gave me the account he said, “Jean-Mark kept telling me about how you manage your sales cycles. We need someone like you on (big account name) because it’s a super complex situation there. That’s why you’re on it now. Good job. Don’t get cocky.”

No more small accounts from then on.

4. Pro Tip: interview like an enterprise seller

The biggest, fastest jumps in a career tend to happen by getting a new role. It’s not that hard to separate yourself from run rate sellers if you can demonstrate you know the path to big deals in big accounts.

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Danny Higdon used to do $20k deals at an early stage startup making $160k all in per year. After we worked together he went for an interview with a more mature scale up. After one interview with the CRO, they abandoned the typical 6 interview process, and told him they would have HR get an offer out to him that day.

In the first interview with the hiring sales manager, Danny laid out how he would approach large banks. He walked the hiring manager through the steps of the Two Mountain model, the framework I teach. Toward the end of the call the manager said, “I’d like to move on to the offer phase. None of the other candidates are talking like you are. We need someone who thinks bigger on our team who actually has a plan. I’ll have my HR person get back to you later today.”

Now his average deal size is $250k and rising. His has gone from $160k to over $300k this year.

You can absolutely go from a mid-market or commercial rep to an enterprise seller in 12 months or less.

To help you execute that I host an upskilling experience, the Elite Sellers Playbook.

It delivers a complete toolkit of everything you will need to excel as a strategic seller - live coaching sessions, a library of on-demand training, templates and assets.

To learn more book a call here.

If you are stuck in the land of transactional, run rate selling, let's pull you up and out fast.

Your current selling reality is way too hard.

And your goals are too important to just let things ride.

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