Are You Ready for Enterprise Selling?

Dan Smaida – Wednesday, December 07, 2016

Over the last several years, I’ve watched (and tried to help) literally thousands of salespeople in multiple industries attempt the transformation to enterprise selling. And in many cases, I’ve seen good sellers fail to make the leap.

Why? Because the day-to-day reality of the enterprise seller is much different than most of us anticipate. And, of course, enterprise selling is harder – in some obvious and non-obvious ways.

The Underrated Differences in Enterprise Selling

Notice – I said “underrated.” This is not a primer on the obvious differences – you’re ready for those! It’s the underrated differences that get you. (Well, not you, because you’ll be prepared in another few hundred words or so.)

Massive, continuous learning curves. Every function in the organization has its own metrics, deliverables, norms, protocol, lexicon, and values – in other words, its own culture. And they vary by customer – each has its own dialect. You have a lot of learning to do, comforted by the knowledge that some of these folks may grudgingly admit that you aren’t so bad…for a salesperson.

Discussing things you don’t understand. You’ll never know what everyone is talking about. There’ll be some days you’ll feel like you don’t know what ANYONE is talking about. And that will never really change – you’ve got to learn to make peace with the feeling, hone your listening skills, and take excellent notes.

Bean-Counters who don’t “get it.” By definition, enterprise selling requires customization, innovation, and out-of-the-box thinking – in other words, things finance and ops often hear as “costly,” “risky,” and “unprofitable.” It’s not their fault – they’re paid to provide a check and balance, even at the risk of being labeled as the Deal Prevention department. Be prepared for a different level of internal selling than you’ve ever experienced.

The ROI Challenge. And I mean “challenge” – the more dollars, risk, and reputations at stake, the more customers challenge you to prove your solution works. Your customer stories and feel-felt-founds won’t help you now – you’ve got to help your customers do the math on the value of your solutions. And that’s a lot harder than it looks.

Turning data into insight. This one is easy to underrate – you’re excellent at, and you know your way around a spreadsheet. But now you’ve got new dependencies and interrelationships to consider – what’s the field for that? And how do all the different opinions and facts you’ve collected turn into a value hypothesis all those different stakeholders will buy? You were doing algebra, and this is calculus.

Management pressure. Even if you’ve already dealt with too-frequent inspections and micromanagement, it takes on a whole new level when the stakes on every deal are so high. I’m not sure you’re ready for the sheer amount of reporting on what you’ve done and explaining why nothing has changed since the VP asked you about it 36 hours ago.

Drought and famine. Even if you successfully navigate these other pitfalls, you’re going to go through long stretches of no progress. The customer is going to go dark. The consultants and procurement are going to keep you in the dark. There are a billion more steps. Even when it goes well, it just takes so loooooooong. You’re going to need financial, operational, and mental strategies to stay solvent, productive, and strong during the dark stretches.

Review: Why Enterprise Selling (Potentially) Sucks

You’ll get hungry. You’ll get lonely. You’ll get frustrated. (And judging by my previous paragraph, it gets dark.) You may even get desperate – I’ve seen sellers pitch some absolutely horrifying concessions in the hopes of bringing one (anyone!) over the goal line. All this in a climate of internal resistance and management pressure. And spreadsheets. And meetings about the spreadsheets.

Reality Check: Are You Ready?

In case I haven’t said this yet: Enterprise selling is not for everyone! It may be for you, though, if you can answer these questions. (Note: This set of questions has evolved from hundreds of coaching conversations I’ve had with enterprise sellers.)

· Am I ready and do I have a plan to put in the work learning new cultures and functions?
· Do I know what I don’t know about my solutions?
· Can I comfortably function from a place of ignorance in front of customers?
· Can I deal with my own impatience with finance and continue to sell for “us,” not the customer?
· Am I prepared to help my customer do the math on ROI?
· Can I construct logical, rational business arguments for actions that change the course of business?
· Will I be able to withstand pressure and criticism from executives who need deals to happen faster?
· Can I really go for long periods without validation without questioning my own self-worth?
· How am I going to keep myself going when nobody’s saying yes and there’s “nothing I can do”?

Summary: If You’re Ready, It’s Worth It

I hope I scared you a little, but not enough to discourage you if enterprise selling is what you want to do. At its best, enterprise selling is extremely rewarding – you’re affecting customers’ lives more profoundly, breaking new ground, and usually getting paid a little more.

Just be honest with yourself, and be ready for some of the underrated challenges that have tripped your colleagues as they’ve attempted the transition to enterprise selling. Good luck!