How to Get Into Enterprise Sales: Skill Sets, Transitioning Tips & More

“This year, I’m hoping not to see any growth in my career! What about you guys?! #squadgoals!”

… said no one ever.

In truth, an employee’s work must involve some amount of challenge if they are to stay motivated—and increasing your salary can definitely be seen as a challenge. Studies show that the financial factor is actually only one of many motivators, and may not even be the most important.

Personal growth and relationships with other people move the needle just as much, if not more, than money and reputation.

So what does this have to do with you? Well, you may enjoy the sales process, and may love the rush you get when closing deals, without growth there’s little to come to work for in the morning.

Add to that the typical daily grind – tons of prospecting and outreach, endless demos, small deals quickly signed and forgotten, always on to the next thing – and you have a recipe for dissatisfaction and boredom.

This is why many sales reps aim to break into enterprise sales—closing large corporate deals that often take months to secure.

Not only is it more of a challenge, and more satisfying when a deal does close, but the daily routine takes on a very different shape.

Now it’s all about:

• Really in-depth prospecting research
• Fewer outreach calls and demos, which are more intense when they do occur
• Speaking to lots more people in a company before a decision is ever realized
• Big (BIG) payoffs when a sale does happen

There’s a ton of opportunity here ... and good news: that’s what we’re gonna talk about today. We’ll take a look at what this niche is, how to break into enterprise sales, tips for making the transition smoothly, and how to get started today. No more new year’s resolutions that involve, ya know, NOT succeeding.

Ready? Read on.

What is Enterprise Sales?

Enterprise sales refers to high-value contracts with large companies, involving bigger deal sizes, complex negotiations, and long sales cycles.

They typically only occur at the corporate level, though other large organizations (a nonprofit, say) can also be candidates for enterprise deals.

The enterprise sales model differs from more traditional SMB sales in that it brings with it a higher level of risk, both for the salesperson who has worked so hard on the deal as well as the company that’s investing so much in it.

Some of the most common industries that engage in enterprise sales include:

• Software as a Service (SaaS)
• Manufacturing
• Insurance
• Financial Services
• Medical Services

In addition to bearing more on some fields than others, enterprise sales has some very specific stages that vary a bit from the typical SMB sales process.

The Stages of Enterprise Sales

While there exist many paths to a successful enterprise sales deal, here is the basic sales process for most enterprise sales:

• Prospecting
• Discovery
• Proposal
• Delivery
• Post-Sale Onboarding and Support

Before you can learn more about how to get into enterprise software sales, or any other type, we need to take a look at what an enterprise sales team usually looks like.

Enterprise Sales Team Structure

Enterprise sales isn’t a solo effort. A full enterprise sales team—sales managers, SDRs, account executives, and customer success—works together to close big deals.

In fact, sales organizational structures can take a number of forms, but for enterprise teams, it usually looks something like this:

• Sales Manager: Leads the team, organizing the sale process and the entire team’s activities
• Sales Development Representative: Responsible for lead generation and prospecting
• Account Executive: Handles the main chunk of the sales process and oversees many business development and enterprise sales strategies. For a deeper understanding of the differences between business development and sales, check out our "Business Development Vs. Sales: What’s the Difference and Why You Should Care?" article.
• Sales Engineer: Assists with tech support and is an internal product expert who helps fit your product into the customer's tech stack
• Customer Success Specialist: Continues to build the relationship post-sale, helping increase the lifetime value of new customers and supporting them over time with customer success strategies

What Does it Take to Be an Enterprise Sales Representative?

Enterprise sales is a sales position, that’s true. If you went to work in this field, you wouldn’t leave all your skills behind, you’d just use them on a much bigger scale.

We like to think of it as the difference between hosting a really sweet party and taking the One Ring to Mordor. Sure, hobbits can totally do both, but one is way more challenging. (And, assuming you don’t incinerate in the fires of Mount Doom, much more rewarding as well.)

Let’s take a look at the main differences between a regular sales position and one in enterprise sales.

Enterprise Sales Job Responsibilities

Enterprise sales does mirror that of SMB sales in the sense that you’re still engaging in prospecting, outreach, relationship-building, nurturing, and closing contracts on a daily basis. Because the stakes are lower in traditional sales, though, reps don’t spend nearly as much time on the same leads and prospects.

By contrast, enterprise sales reps must deeply understand each target organization—its decision-makers, buying process, and pain points. They need to know all the moving parts at that organization, who answers to whom, how decisions get made, and which departments will ultimately have a say in whether they will get a “yes” or a “no.” That involves a lot more time and research.

Enterprise Sales Career Experience Requirements

Ideally, an enterprise sales rep will already have quite a bit of experience in general sales. This gives them the know-how and confidence they need to approach really big accounts. It’s true that such experience isn’t always required, but it does go a long way.

The Payoff: Typical Enterprise Sales Salaries

One of the main benefits of being an enterprise sales rep is that you don’t have to chase down new prospects or decision-makers as frequently. Because enterprise deals constitute more complex sales, business development takes longer – i.e. the enterprise sales process in general – but the results also last longer, with typically longer contracts and less lead gen in between.

Another of the big benefits? You get to add some big brand names to your book of business, which is great for your own personal selling reputation and future career prospects.

Plus, the salary is nothing to sneer at. Enterprise sales reps can pretty easily earn six figures, according to the data. Glassdoor gives an average salary of $141,000 annually, while ZipRecruiter estimates about $76,681.

If you average the averages, we’re looking at about $108,333 per year, give or take a few pennies. Sound good? Here’s how you can work toward your new career today.

How to Become an Enterprise Sales Representative: A Step-by-Step Guide

So you’re ready to move away from SMB sales, and into enterprise sales. Here’s how.

Step 1: Pick Your Industry

If you’re changing roles, this may be an opportunity to change industries to something you find more interesting than your current field. Enterprise sales reps are expected to have all the answers—or at least know how to graciously request to find out and follow up.

Regardless, it’s absolutely essential to be totally up to speed on the industry you’re looking to sell in, if you aren’t already. You need to know it like the back of your hand, so that when you come across a worthy prospect, they’ll see you as worthy as well.

The takeaway: Study your chosen industry. Read trade magazines. Go to seminars or conferences. Talk to mentors and decision-makers, even when you’re not hunting down a deal. Learn like it’s your job … because it is!

Step 2: Up Your Education Stats

If you want to run with the big dogs, you need to live and breathe sales. But that starts with knowing the full fundamentals. Even if you have an innate knack, it can’t hurt to underline your credibility with a certification program or two, such as the ones offered by Northwestern or Columbia.

Step 3: Gain Hands-On Experience and Build Skills

Ideally, you’ll have at least a few years of experience under your belt before going for an enterprise sales job. That gives you time to gain and sharpen your sales skills. But if you’re looking to brush up on those skills now, here’s what we recommend:

• Enhance your communication: Communication is a natural skill for some, difficult for others. If you struggle to speak confidently, you’ll need to actively improve your communication skills. Courses such as Toastmasters or simple university speech classes can help.
• Practice active listening: Active listening is hard, because we always want to jump in with the counterpoint or the sell. Don’t. Instead, promise yourself you’ll always count to 2 after someone finishes speaking before you jump in. You’ll be surprised at what you let yourself hear.
• Identify pain points: Pain points are the keys to the kingdom. Learn to hear what your prospect is struggling with, and you will have all the material you need to solve their problems.
• Show, don’t tell: Promises, promises. We all know sales reps can be convincing. However, it’s not until we see something work with our own eyes that we’re actually convinced. Build presentations and demos that show the worth of your product firsthand and bring them to every meeting.
• Cultivate brevity: Why spend an hour on something that you can accomplish in 20 minutes? Not only do you save yourself time to work on more important activities, you communicate to your prospect that their time matters to you as well. Edit your content ruthlessly: sales scripts, presentations, demos, business collateral, you name it.
• Build relationships: Yes, it sounds obvious, but some reps aren’t that good at relationship-building. Enterprise sales is all about it, however, so work on those skills. Practice your pitches endlessly, look up a few jokes, do your due diligence to learn all about your prospect, and generally treat your relationship with them like it's worth its weight in gold. Because it just might be.

Step 4: Create an Eye-Catching Resume

Your sales resume matters, and all companies will want to see it before they consider offering you an enterprise sales job. When you need to send off a CV, make sure it:

• Draws attention to your main accomplishments up top
• Includes big brand names with whom you’ve worked in a visible location
• Uses numbers and stats prominently
• Is tailored to the specific company you’re applying at, highlighting the successes meaningful to them
• Uses keywords judiciously, especially if you’re using your resume online (e.g. LinkedIn)
• Speaks to the prospective employer’s vision of what they’re looking for in a new rep

Also, make sure to include a cover letter that is concise, highlights your skills, and is easy to read.

Step 5: Nail the Interview

Most hiring managers are looking for enterprise sales reps with charisma, self-motivation, and a history of success. They want to know you have a range of sales skills and aren’t afraid of the down and dirty tasks, like cold calling. But mostly, they want you to sell them on you, because you’re the main tool they’ll use to land big contracts.

You can prove your worth with open smiles, confident handshakes, ready sales reports, and a willingness to answer all questions without hesitation.

It also helps to prepare some anecdotes ahead of time. Think that moment you almost lost a sale but didn’t; the time you snaked a big contract from a competitor; or how you discovered XYZ Megacorp was ready to make a change before they even started looking.

Tips for Making the Transition to Enterprise Sales

Once you’ve landed the enterprise sales job, it’s up to you to ensure you’re worthy of it. If you want to rock your new role and continue to level up your sales career, it’s time to kick things into high gear. Here’s how.

Be Laser-Focused on Your Goals

It’s important that you always make sure you and your sales manager are on the same page. Know what your goals, metrics, and KPIs are at all times. Find out how the sales process works in your new role, what top sellers in your department do, and how it all fits together.

It’s also important to make sure you and everyone else on your B2B sales team stays motivated - after all, you can’t land an enterprise deal all on your own. If a winning sales commission structure doesn’t yet exist at your company, reach out to your sales manager and see if you can help to build it! That benefits everyone who’s a part of the sales process.

Look for the Right Prospect

In enterprise sales, it’s more important than ever to find the right prospect, because you spend so much time on them compared to SMB sales. This is especially true if you’re an enterprise sales rep for a startup, because resources are very limited.

Zero in on the most ideal enterprises in your industry, then work to really uncover everything you can: the people at each company you’d ideally end up speaking with, what each person is responsible for, and what each person’s pain points are.

Of course, using a good CRM will help you keep detailed notes about the decision-maker, their company, their existing solutions, and anything else to know about their large-scale company—but we may be a little biased there.

Prepare for New Needs, Priorities, & Goals

Large enterprise sales are different from regular SMB B2B sales (acronyms, much?). If you want an enterprise deal, then be aware that enterprise customers will expect more of your time, require more meetings, ask the same questions more often, drag their feet longer, require greater legal due diligence, have a longer sales cycle, and so on.

Salespeople who aren’t cut out for that will be frustrated at best.

Expect a Longer Sales Cycle

Again, you’ll want to expect a long sales cycle. It’s not you; it’s just the buying process for enterprise deals and for decision-making at such an elite level.

If you go into your new role knowing that the overall process simply takes longer, you’ll have an overall much easier go of it. And if you learn how to shorten the sales cycle, all the better!

Perfect Your Relationship Skills

As we’ve said above, building relationships is crucial for enterprise sales. Consultative sales is key to this, because it turns a simple sales pitch into a conversation that has worth for your prospect even if you don’t close the deal. That makes them less wary of you and helps to generate trust.

The best way you can build that trust is to ensure you keep all the information at hand, which is why you’ll need a good customer relationship management (CRM) tool.

Be Willing to Talk to Anyone

This is true generally speaking in sales, but in enterprise sales, you'll have more than one contact at a company. You'll be passed from department to department, stakeholder to stakeholder. True sales professionals will expect this out of the enterprise sales cycle and will stay cheerful, happily answering the same questions on repeat. Bonus points if you manage to tailor your responses so that they speak to a solution for each department’s problem areas.

Be Extra Prepared to Show Your Product’s Value

In enterprise deals, it takes more than just a few nice-looking progressive growth charts or raving customer testimonials to close the deal. No, to be an effective enterprise sales rep, you need to come equipped with detailed case studies, white papers, news clippings, and more showing your business as the front-runner for your industry.

More than just telling them the solution to their problem, or even showing them how your product solves it, if you can back it all up with cold hard published facts, you’ll certainly leave a lasting impact.

Get Your Enterprise Sales Career in Gear

It’s a lot, we know. That’s why you need somewhere to organize all your contact information, customer insights, notes, thoughts, and feelings. (At least three of those, anyway.)

That’s where a CRM like Close comes in. It’s the perfect addition to enterprise selling – or really a sales career of any kind. When you work with enterprise companies, it’s critical you don’t lose track of a single detail relating to such a huge deal – and Close will help you prevent that.

On a final note, if you want to learn more about enterprise sales so you can close deals like a boss, even at the highest levels, our free resources and tips for enterprise sales will get you there. Get our book on enterprise sales: