Here’s a fun fact: just 10 percent of all minor league baseball players make it to the majors. The minors are full of exceptional athletes who’ve excelled at every level, but only a fraction can handle the sharper curves, bigger crowds, and intense pressures of a big-league season. For sellers, making the shift from selling to SMBs to Fortune 500s is just as hard—but it doesn’t have to be.
There are a lot of new factors to account for at the enterprise level, and if you’re not prepared, you could quickly find yourself in over your head. Here are the curveballs you need to look out for and how to knock them out of the park.
What to Expect at the Enterprise Level
Whether you’re an ambitious SMB seller switching teams or a sales leader looking for more prestigious logos, here are the realities you face once you take the plunge.
Longer sales cycles
The sales cycles are going to be long—like, really long. If you’re used to selling to SMBs, this can take some getting used to. The ultimate pay day might be nice, but it’s going to take some time to get there, and you have to keep the deal moving and prospects interested and engaged from start to finish.
This means understanding what matters to every stakeholder in the process, from end users all the way to procurement, and being able to structure your narrative to address each party’s pain points. You’ll also need to find ways to keep the conversation going, which can range from using content strategically to finding new ways to add value.
Nebulous org charts
Selling to SMBs usually means convincing one or two people that your solution is what they need. Once you go up market, you’re looking at convincing an average of almost seven people per deal. To make matters even more challenging, you can’t rely on an org chart to point you to the decision-maker. While the VP or CXO should be final authority, the reality is rarely that simple. There are all sorts of influencers and cranks in the mix, too, so you’ll need a bit of inside help to navigate successfully to a close.
Once you’ve turned your prospect into your champion, he or she should be able to clue you in to who’s who, but going into the first meeting with insider insight can be a game-changer. A little debrief from a current or former employee who’s familiar with the team and the company’s buying process can help you get to closed-won a lot faster and without having to dodge so many obstacles along the way.
At the enterprise level, you’ll be met with more and fiercer competition than you’re used to from your SMB days. Everyone in your space is going after the same Fortune 500s, but there’s only so much business to go around.
The competition will be breaking out their big guns to woo buyers and the buyers themselves will be savvier as a result. The tactics you’ve relied on before may no longer be enough to help you stand out from the crowd, so you’ll need to rethink your approach to differentiation.
Enterprise buyers are so inundated with outreach that just taking the time to ask them questions about their current business challenges—rather than just steamrolling through you pitch deck—can be a breath of fresh air. This will help you understand their needs and enable you to craft a deal designed to address them. Or even better, do this research beforehand, so that you can tailor your messaging from the get-go. The bigger the business is, the more this personalized approach will help you stand out.
More End Users
Training one or two end-users on how to use your product is a lot different than training the dozens—or even hundreds—that your company will have on its hands after landing an enterprise contract. If your training strategy doesn’t scale effectively, users will soon grow dissatisfied with your solution and eventually stop it them altogether or complain loudly enough that your contract becomes a churn risk. Each user needs to be able to harness the full power of your solution, and while it’s not your job to train them, you definitely have to factor that into the implementation plan and overall customer success journey.
During the enterprise sales process, make it clear that your organizations will gladly host training sessions at your client’s workplace, and schedule quarterly reviews to stay on top of any challenges they may be having. Conduct webinars or provide computer-based training modules that dive deeper into one or two specific features that, once mastered, could really address your buyer’s needs.
Expand With Ongoing Value
Keeping business at the enterprise level will be just as hard as winning it. The deal may be done, but the real work is just beginning, and you’ll have to put in extra effort after closing to maintain and grow your accounts.
With so much competition, you need to constantly stay on top of what’s working and what isn’t to emphasize your product’s strengths and eliminate its weaknesses before they can wreak any real havoc on your ability to retain customers.
One way to do this is by going straight to the source: your clients. After compiling your first cadre of blue-chip buyers, sit down with the key decision-makers to learn what motivated them to sign a contract. Go into everything from the main pain points that your product is addressing, it’s weaknesses in their eyes, and even who else they evaluated from the competition before choosing you.
If account expansion is already on your mind, you need to make it impossible for your clients to miss just how much of an impact your solution has had on their businesses. That means defining a clear set of KPIs that measure and illustrate how your solution has improved on the areas that matter most to them.
Today’s buyers have made it clear: they want better partnerships with their vendors—not one-time transactions. And if you stay engaged with them, you’ll not only be providing a better customer experience and positioning yourself to expand within the account, you’ll also be gaining insight into what has made you successful at the enterprise level thus far—and that’s knowledge you can use to help you set the course on future sales.
Break Through With Inside Insight
Selling into the enterprise isn’t always an uphill battle. Sometimes it’s as simple as knowing who to talk to. No one knows all the quirks and hidden snags of their company’s purchasing process than someone who’s actually worked there.
If you’ve been working with an advocate inside your prospect’s organization or are in contact with a recent former executive, lean on them for insight into common issues at all stages of the sales cycle to avoid them and keep the momentum going.
Inside insight can also help you get a better idea of which decision-makers you should be targeting. This can be a huge advantage. While your competitors may be able to put on a good show for buyers, if they’re performing for the wrong audience, they’ll never get a deal done.
The key to standing out at the enterprise level is all about personalization. So once you learn who to target, find out what to target them with. Your inside contacts can help guide you in the right direction about the pain points you should address, the pet peeves you should avoid, and what time of year is best to reach out.
Chances are, your competitors will be overlooking these critical details, so the more you can tailor your approach to align with exactly what your buyers want to hear, the better. This personalized approach has the power to make a real impact—regardless of the size of your prospect’s organization.
Making the move up market is a big and exciting step, but you need to be prepared in order to make it successfully. When selling into the enterprise, you’ll be met with longer sales cycles, bigger contracts with higher stakes, and fiercer competition. Due diligence and inside insight can help you conquer these challenges. By knowing what to expect from the buying process and understanding the message that your big-time buyers’ want to hear, you’ll be able to cut through the noise and move up market without a hitch.