The Enterprise Prospecting Guide: 6 Tips for Better Responses


Prospecting in the enterprise environment is just different.

Enterprise is generally behind the times and slow to move on new ideas. Their calendars are blocked with 76 meetings. And finding time is tough compared to an SMB executive. On top of that, you have multiple decision makers to be looped in.

And to make it worse, everyone and their start-up cousin is calling them, which makes it tremendously difficult to stand out.

On the flip side, however, the Enterprise segment offers a vast number of decision makers to go after, and, as we all know, there is a big payoff if you can win the deal.

So, today, we’re going to cover four prospecting tips for breaking into Enterprise Accounts (plus some bonus tips at the end).

  1. Shifting your mental game
  2. Building rapport with prospects
  3. Leveraging information to become your prospects doctor
  4. Leaving every call with new pieces of information

Tip #1: Shifting Your Mentality

Before you approach an enterprise account, you need to get the space between your ears ready to go for the day.

Let’s take a look at NFL quarterback Russell Wilson’s pregame routine, for example:

  1. He watches past videos of successful plays (Visualization exercises)
  2. He listens to music with positive lyrics only (Eliminates the self-doubt & fear)
  3. He then goes through a series of neutral statements & affirmations (Focusing his mind on positives)

Russell prepares to win by preparing his mindset.

Look, Russell Wilson might be an extreme example because he’s spending thousands of dollars on performance coaches. However, Russell only plays 16 – 19 games every 365 days. As a sales rep, you have game days every day, with only a few sprinkled in practice sessions.

Luckily, there are a few things you can do today to start improving how you go about the rigorous, rejection-filled prospecting days.

Believe in your product

Chances are you’ve heard the advice, “Don’t sell something you don’t believe in.” And while this is great advice, you probably wouldn’t have taken the job if you weren’t fired up about the product or service.

The trick is that believing in your product isn’t some one-and-done thing. It’s a mindset you need to get into every day.

You need to go into your day KNOWING that your product is the best thing for your prospect.

Before you start your prospecting blitzes, try a few of these to shift into the state of believing in your product or service:

  1. Write down 3 reasons you joined the company (i.e., I joined X company because of the amazing culture, I joined x company because of the earning potential.)
  2. Write down 3 problems your product solves (i.e., Our product alleviates the need to send out direct mail to collect payments from customers.)
  3. Read 2 customer stories or testimonials (i.e., Go to your company website and find the testimonials. Or find a customer video on YouTube to watch.

Sell time on your calendar

If you’re in the Enterprise space and can close in 1 call, please leave a comment below and teach me your ways. You can even write the next blog. For the rest of you, listen up.

Selling a product in the Enterprise space takes time. Lots of time. And many many calls and meetings.

That means your number 1 priority, especially early on, needs to be getting those calls.

Early on, you’re not selling your product. You’re selling time on your calendar so that you can build a relationship with the prospect and have the opportunity to sell your product later.

This takes a mindset shift.

There are usually two types of sellers who struggle with this. The first type of seller knows the product like the back of their hand. They tend to feature dump and forget the purpose of a cold call.

The other tends to overthink the situation. The thoughts are racing, and negativity starts to pour in.

Trust me. I’ve been there.

To solve this, take a step back, focus on your mindset, and believe in your product (like I mentioned above). If you truly believe in your product, you won’t feel the need to feature dump right away. And if you prepare your mindset, you’ll get rid of a lot of those negative thoughts.

Now that your mentality is shifted and you’re ready to dial until your fingers fall off (please get a dialer), what should you do when they finally pick up?

Tip #2: Build Rapport in 15 Seconds

Everyone wants to win business with the big fish. Every company wants these big logos listed on their company website. As a result, most qualified prospects in the Enterprise space are also being prospected by every other SDR or AE around.

This million-dollar question becomes, “How do you stand out from the rest?

Building a rapport with them is one of the best ways to do that.

Building rapport is important in every segment, but in the Enterprise space, it is even more vital. Other segments can come down to a numbers game. With enough calls and emails, you can usually find a way to break through.

That’s not the case with Enterprise.

The next question you may have is, how do you start building rapport when you only have 30 seconds to make an impression on a cold-call? Where do you draw the line between beating around the bush and getting right to the point?

Here are a few simple tactics to use when trying to bring down a prospect’s guard:

Making the conversation about the prospect

It is very common for salespeople to forget the point of a conversation. As a result, a salesperson will naturally jump in and tell the prospect why they are calling.

The problem is that It’s not about you. It’s always about the prospect.

Instead, ask simple questions like, “How’s your day going?” or, “How have you been?” This is a simple fix that can gear the conversation towards the prospect.

From there, it’s great to add a little humor. When the prospect responds back with “Fine, how are you?” hit them with a simple, “You know I was doing alright, but now a lot better since I’m talking with you!

The moral of the story is this: make the prospect feel appreciated, and don’t make them feel like you’re using them.

Show gratitude

People are busy. They don’t have time for cold calls. Maybe that’s why when you pick up the phone and start to pitch, prospects will hangup or say they are running into a meeting.

Again this comes down to making the prospect feel appreciated. Simply thanking the prospect for taking the time to answer your call will go a long way.

People love to make other people’s days, so if you make it seem like the prospect made your day by picking up the phone, they will be much more receptive to the conversation at stake.

Show empathy in sensitive times (COVID-19)

I learned this one the hard way. Pretty soon after the COVID-19 outbreak in March, offices shut down, businesses were going through layoffs, and no one knew what to expect. The world was in a complete standstill.

I had the worst week in my sales career and thought I was doomed moving forward.

This led to a lot of confused and angry prospects calling me insensitive for making cold calls.

I didn’t know whether to acknowledge the elephant in the room or keep doing what I had been doing for the last year.

I had to adjust. But cold calls are my prospecting strength, and I couldn’t just replace what was generating 90% of my meetings.

As a solution, I learned how to empathize with my prospects about the current world and selling climate.

On every call, I’d ask my prospects if they were staying safe and healthy, how they were coping with the move to a remote atmosphere, and how they were staying sane being in the same house all day.

All of this is to show the prospect they are not alone in these tough times.

Tip #3: Become Your Prospect’s Doctor

Personalization, personalization, personalization. Every sales rep has heard this once, twice, or a million times in their careers.

Personalization is a necessity in every level of sales. It’s what catches the prospect’s attention. An author would call it “the hook”. But there are right and wrong ways to use personalization, especially in the Enterprise space.

The days of leveraging someone’s college, hometown, favorite sports team, etc., are out the door.

Now, as a salesperson, you need to go one step further and make your personalization relevant to their current business initiatives or pains.

How do you do that?

Know how to navigate a 10-K & Annual Report

10-K’s are undoubtedly my number one source of personalization when prospecting VPs and C-Level executives.

ONLY VPs and C-Level executives.

The reason for this is that frontline managers are often too far removed from what takes place at the executive table. They care more about their day-to-day and their current initiatives than fiscal planning.

So, why use a 10-K report?

Every public company is required to publish a 10-K each year, mandated by the SEC, and it consists of a comprehensive summary of a company’s financial performance.

Within a 10-K you can look at fascinating revenue numbers, company initiatives, industry trends, and other wonderful nuggets of information that you can use for prospect personalization.

Now, if you go look into a 10-K, you’ll likely feel overwhelmed. Imagine trying to read through a whole document of 200+ pages just to find one small piece of personalization.

You’d probably think it’s not worth your time… Oh, but wait… IT IS.

The key is to engage smarter.

First, use keyword searches. All it takes is a simple “Command F,” and then it’s plug and play.

Obviously, each salesperson looks for different information, but for me personally, I look for words such as “competition,” “technology,” “revenue,” “initiatives,” “third-party,” “vendors,” etc.

From there, just quickly reading the various snippets in relation to those key terms might lead you to the information you are looking for.

Next, look for the 1A: Business Overview. This is the gold section where you should spend the majority of your time learning and educating yourself about their business.

There are several subsections you should focus on:

  • The mission statement
  • Sales
  • Marketing
  • Distribution channels
  • Partnerships
  • Competition
  • Growth strategy
  • Manufacturing
  • Subsidiaries
  • Business unit overviews

Take what you need, and implement the information into your emails & cold calls.

A great example of examining a small portion of 1a business overview is Intuit. You can see this in the picture below.


Next, dive into the 7A: Management’s Discussion & Analysis. This section is where company executives analyze the company’s performance.

A salesperson can find extremely valuable information regarding risks, new projects, goals, and future plans. What better way to personalize than to use their own executives’ words against them?

My favorite example of leveraging 10-K research came when reading through the Management’s Discussion & Analysis of one of my Target Accounts.

I noticed that over the last fiscal year, the company had pumped in an additional $188 M (33% increase) of marketing dollars in their go-to-market initiatives as they were looking to bring new products to market.

Lastly, look at the press releases and news sources. Here, you can uncover financial statuses, market research reports, internal news about their strategies, new hires, and more.

Take a look at this article that I’m currently using to prospect executives at WeWork.

I uncovered that the CEO is focused on profitability in 2021. The way they planned to accomplish this is through added-value services and amenities, better payment options, extending internationally, and increasing the average lease term to 13 months.

I used this messaging in my emails to executives, attached potential hurdles they could be facing to achieve these goals, and shared how my company could potentially help.

I challenge you to search your prospect’s company right now and see what you can uncover. It might open a door for you.

But please don’t spend more than 20-30 minutes finding the information you need. You can always come back to Google or a 10-K report in a few months to find new information if you still haven’t opened a door with what you have.

Tip #4: Leave Every Call With New Information

If you have a prospect who isn’t playing ball or is giving you a referral rather than a sale, you have one goal to consider the call a success — leave that call with new, relevant information to leverage in your next call.

The reason this is so important for Enterprise level accounts is because it takes time to open doors in the Enterprise space. And if you can get a warm referral, mention a conversation, and uncover new information along the way, you’re just giving yourself a higher batting average.

Diving into Google news and using LinkedIn to uncover information on an account is helpful in your pre-outreach. However, wouldn’t you rather get that information directly from your prospect?

On top of that, breaking into Enterprise accounts can be a lengthy process. I’ve had accounts with no traction for upwards of 6 months. So anytime I got a prospect on the phone I make sure I use my time wisely.

There’s a few things you can do here to ensure you always leave the call with new information.

Ask the right questions

Make a list of your top 3 value-driving questions by persona.

What does your customer want from your product to make it a no-brainer?

What would make them consider your product as a success or a failure for them?

The exact questions will be different depending on your product, your prospect, and your relationship.

These are the kinds of questions that you can maybe answer yourself through intensive research, but if you can get a prospect to answer for you, that is a big win (even if you don’t make the sale yet).

Getting a referral

If your prospect just left the company, or their responsibilities don’t align with what you offer, it is crucial you ask who you should be reaching out to.

Ask, “Is it a bad idea to ask you who I should be contacting for a chat around (insert problems you solve for)?

And follow up with, “How should I approach (prospect name)?” and, “What will be top of mind for them?

Bingo. Now you have a warm lead. Make sure you reference the previous conversation with the new prospect. It will help put your new prospect at ease.

Prospects not playing ball

This is very common today. Which is one of the reasons multi-channel approaches are so important. You allow your prospect to respond on the medium they choose.

But regardless, you’re going to experience tons of rejections and prospects who don’t want to deal with you.

It’s just the reality.

Other than your amazing objection handling skills, how can you combat this to come away with information?

Ask a super short and specific qualifying question.

Hey real quick, and I’ll let you go. Is your team using X product?

What’s top of mind for your team right now as it relates to (insert problems you solve for)?”

Use this information in your follow up with this prospect or others in the account.

Bonus Tips


One of the difficult parts of selling in the Enterprise space is that there is rarely one person that makes a decision. Typically, multiple individuals within various departments and business units need to be involved in a complex deal in the Enterprise space.

While you may have gotten a meeting with one Marketing leader, you are still going to need more people involved to help progress the deal.

Make sure you have a solid, multi-thread strategy in place along with successful account mapping so you can take your deal to the finish line.

RELATED: The Tactical Guide to Multi-Threading Sales

Make Use of Those Around You

Fun fact, every person in the world is connected by 6 Degrees. Just because you aren’t connected with a prospect doesn’t mean the person sitting right next to you isn’t.

Even better than the person next to you, imagine having your CEO reach out on your behalf. I’m sure that would catch the attention of someone you’re prospecting.

I find it that most people don’t take advantage of these resources because they believe they are being a nuisance, or they are intimidated by their leadership teams.

We already do it everyday when prospecting leaders at other companies, but all it takes is a simple ask to your own leadership teams.

Sell Fearlessly

Enterprise sales is an intimidating beast to break into. But if this guide has taught you anything, I hope it’s this — the fundamentals of sales are the same at every level.

You probably noticed that a lot of these tips are important when selling to SMB as well.

When you’re doing enterprise prospecting, it’s just a matter of tweaking your thinking, making small adjustments to your process, and going in with the right mindset.

So, have faith in yourself, and go catch yourself a whale!



Brennan Vaughn

Enterprise SDR at


Kyle Herman

Sales Development Team Lead, Enterprise at



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