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Enterprise Selling: Guide to Closing 6-figure Deals (2024)

For SDRs accustomed to SMBs/mid-market sales, enterprise selling is daunting.

The companies are bigger. You have more people to talk to. And there isn’t just one decision-maker; there are whole tribes of decision-makers you must win over!

That said, we’re here to tell you that enterprise sales isn’t impossible; it’s just different.

To help you make sense of it and to get you started on your own enterprise sales journey, we’ve called on the expertise of Al Zia Pervaiz and Simon Waller, two of Cognism’s top AEs and Josh Knipe, Cognism’s former Head of Enterprise Sales.

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What is enterprise sales?

Enterprise sales involve selling products or services to organisations considered to be at an enterprise level. Factors such as the number of employees within the organisation may determine this.

Selling to enterprise customers involves working with large companies with many employees and decision-makers. Salespeople in this space must navigate complexities and build relationships to close deals.

What is the difference between SMB and enterprise selling?

Enterprise selling has longer sales cycles than SMB and mid-market sales. Why? 

Because deals with enterprise-level organisations can take months or even years to close. This is due to larger budgets, more stakeholders, and complex decision-making processes.

So, how does the B2B buying process differ between signing 15k deals and signing 200k deals?

We asked Josh Knipe, whose team, during his tenure with us, smashed record after record - including signing Cognism’s biggest-ever deal!

“The sales cycle for smaller deals is a lot easier. It’s shorter, and there are fewer people involved. In an SMB/mid-market deal, you might deal with one person, maybe two - the CEO and the CRO.”

“It’s very different in enterprise. To close a 6-figure deal, you’ll be talking to people in all parts of the business at all levels. You’ll talk to people in legal, procurement, IT, and finance departments. At the SMB level, those departments don’t always exist.”

“So discovery is critical in enterprise. You have to understand the challenge you’re trying to solve for every one of those stakeholders.”

“It’s also vital to keep on top of the timeline. You have to ensure you have a schedule the client agrees with. That will help to keep you focused during a long enterprise sales cycle.”

Why do enterprise sales?

Why bother with enterprise sales if it’s so complex and time-consuming?

The answer lies in the potential for massive revenue growth.

Enterprise deals typically have higher contract values. Each deal closed can result in substantial revenue increases. Additionally, landing a few key enterprise clients can provide stability and long-term success for your business.

There are also opportunities for upselling, expanding your product offering, and building long-lasting relationships with influential clients.

While enterprise sales may be more challenging than SMB or mid-market sales, the potential rewards make it a worthwhile endeavour for ambitious sales reps.

Implementing an effective enterprise sales process

To succeed in selling to enterprise-level organisations, you must deeply understand their businesses. This involves thorough research, asking the right questions, and providing tailored solutions.

It’s not just about selling a product; it’s about building trust and adding value to your clients.

So, how can you implement an effective enterprise selling process?

It starts with discovery 👇

1. Cold call discovery 

Josh said: 

“Don’t start by overwhelming your client with product features! Instead, dig into what their expectations are.”

“What do they want to get from using your product? What’s important to them? Then align their expectations with what you offer.”

“Do this by asking a lot of open-ended questions. I call this ‘peeling the onion’. The prospect may say they have a problem with something, but what’s the cause? You don’t just dig into the first layer. You have to get to the root of the problem.”

“If all you’re doing is staying on that surface level of discovery, you won’t close enterprise deals. Additionally, you must understand who else in the company must be involved in the deal.” 

Here’s a list of questions to ask:

  • What do the company’s internal processes look like?
  • What other decision-makers must loop in to close the deal?
  • What’s the company’s procurement process?
  • How long might the legal process take?
  • Have they ever closed a deal of this size before? Is this process new to them, too?

2. Lay the foundations for relationship-building

Relationship-building is crucial in enterprise solution selling. Building strong connections with key decision-makers helps navigate decision-making processes and close deals.

But what if you can’t always get straight to the main decision-maker? 

You’ll need to create an internal champion.

These are people who don’t have decision-making power but have company influence. Internal champions act as your salespeople on the inside, banging the drum for your product and persuading decision-makers to take action.

Josh said:

“For me, this process starts right at the beginning with the prospect’s first interaction with your brand. It’s usually through engaging with your company’s marketing materials or talking to an SDR. These things are important because they educate prospects about your company; they lay the foundations before conversations happen.”

“It helps if you have a great B2B marketing team. We’re fortunate enough to have this at Cognism! There are many resources at the sales team’s disposal - so by the time I get involved, people already know what Cognism does.”

“My job is to start a dialogue  and discover the prospect’s pain.”

To cultivate internal champions, Al Zia Pervaiz likes to offer them something:

“When I find a good internal champion, I ask them: who are you struggling to get hold of? Give me five people you don’t have details for. I’ll give you the data in return for an intro to the decision-maker. It’s a nice freebie that can get you in front of the decision-maker quicker.”

Of course, he’ll then face objections: 

“Sometimes, people can be reluctant to give out their boss’s name, even if you offer them a freebie.”

“In this case, try not going up the chain, but sideways! See if there’s another individual in another department who can help. Gather as much information about the company as you can.”

Another common sales objection he sees is:

“Send me an email. I’ll show my boss, and we can go from there.”

The way Al handles this objection is to say:

“Given that you’ll be an end-user for the platform, would it be worth seeing it?”

“You’ll see it in action. You’ll get a much better understanding of how it works. You’ll also be able to sell it to your boss and answer any of their questions yourself.”

The key to creating an internal champion is to show them the value the tool can give to them as an individual. Once they recognise the value, they’ll work alongside you to promote your product to others in the company.

3. Do your research

How do you navigate enterprise organisations and deal with a slew of prospects at once?

Here’s Josh’s advice:

“You have to understand how global companies operate. The biggest corporations in the world, like IBM or Dell, always operate in silos. What you have to do as a salesperson is to interact with each silo, discover who has decision-making powers in each and then find out who they report to.”

“Leverage the networks inside those silos to give you more information about the different units. This means you can branch off into different departments or even business territories. It’s a multi-threaded approach; you’re prospecting to potentially dozens of people simultaneously.”

“You also have to present those silos with specific use cases for your product. For example, how sales will use a product might differ greatly from how marketing will use it. You must get buy-in from each department head before you move upwards to the final decision-maker.”

“If you have those internal champions on your side before you reach the CEO, closing the deal will go much more smoothly.”

4. Take care of admin

Being on top of timekeeping and admin is always crucial in a SasS sales role, but never more so than in enterprise prospecting.

Al relayed some excellent tips for enterprise time management:

“Get rid of all the white spaces in your calendar! Block out everything. Block out hours for calling, sending emails/follow-ups and sales admin.”

“It’s imperative to be structured. In mid-market/SMB, you’re mostly on the phone all day. That happens less with enterprise, but you’ll do more research and fact-finding. It’s more admin-intensive, so you must be prepared.”

10 tips for enterprise strategic selling

Successful enterprise tech sales requires a strategic approach. These can include many factors. We’ve narrowed it down to ten 👇

1. Find good-fit companies, not just famous names

This is the crucial first step in Al’s enterprise selling process.

“As in B2B prospecting to SMBs/mid-market, find a good-fit company for your product or service. Resist the temptation to just go after big names or famous brands.”

“Instead, have some criteria in mind, then check your target orgs against your criteria. Do they match?”

Here are some example criteria used by Cognism’s B2B sales team:

  • Is the company hiring more sales staff?
  • Is the company expanding into EMEA?
  • Is the company using a competitor?

2. Map the company’s internal structure

Al stressed the importance of taking this step.

“After you’ve found a good-fit company, what you have to do next is map that company from bottom to top. To make enterprise sales successful, you must speak with people across the company - from SDRs to managers, directors and the C-suite.”

“You’ll need a good understanding of the company structure, who sits where and who reports to who. And you have to go deeper than just job titles because job titles can be misleading.”

Al shared an example:

“You can have Sales Directors who are actually just Senior SDRs. So you must understand not just who that person is and where they sit, but their responsibilities too.”

3. Prospect to juniors first

Once you’ve mapped the company and the people inside it, the next step in enterprise strategic selling is to start prospecting!

But where to start?

Easy - at the bottom!

Simon Waller explained a unique outbound sales approach:

“Start with fact-finding missions. We start from the bottom up and talk to SDRs and middle management. We get to understand the company’s processes and pain points.”

“Then we tailor our pitches to different stakeholders - it’s the company’s own information that we’re using and, because of this, it’s information that has real clout with the decision-makers at the top.”

Simon shared a practical example:

“If an SDR tells us they’re using a competitor of ours, but they don’t like the data, then we can take that pain point and use it in our messages to the leadership team.”

Simon recommended this as a good course of action for enterprise fact-finding:

“Start by contacting 20-30 junior people in a sales cadence. Start by cold calling them initially, then expand your cadence with emails, LinkedIn messages and videos.”

“I’d recommend using multiple channels to prospect. Enterprise orgs are large and contain multiple layers. It can take dozens of LinkedIn notes, emails and phone calls to break into a company!”

4. Focus on pain points

Uncover their pain points when you’ve got a junior on the phone.

Information-gathering and metrics fuel Simon’s discovery questions:

  • What tools are they using to generate new business? Are they using a competitor?
  • What’s your least favourite thing about the tool? This gives you a pain point you can use in your pitches.
  • What impact does that have on their performance and their team’s performance? This gives you a metric to strengthen your pitch.
  • Who’s responsible for implementing the tool? With any luck, the junior will give you the name of a decision-maker to prospect to.

Simon told us:

“We take the junior’s answers, then we go to their manager or director. We use the information from those answers to form a pitch.”

An enterprise sales pitch will look something like this:

“We’ve spoken to (junior name) in your team. We know you’re using (competitor name). We know they’re struggling with (pain point), and we know that’s causing a drop in (metric). Here’s how Cognism can help…”

Simon gave us some more tips:

“Discovering pain means you can match that pain to a specific department.“

“For example, if you find out from a junior that bounce rates are a problem, you must speak to the Head of Marketing. If you discover that GDPR compliance is an issue, you must knock on the Head of Legal’s door.”

5. Get buy-in from different departments

When prospecting to an SMB, you might only speak to one person - the Sales Director or CEO. Prospecting into enterprise, you’ll talk to many people in different departments.

The trick here is to get buy-in from all those departments simultaneously. If you’re speaking to sales, marketing, and RevOps, you must align them with your product before you initiate a demo.

Al shared his advice on how to do this:

“Learn how people in different teams respond to things. For example, if you’re contacting Legal, don’t send automated emails - they’ll see through it.”

“Let’s say the company is using a non-GDPR-compliant competitor. You can then email their legal team to ask if they know that. The idea is to approach people in ways that are most relevant to them and will make them sit up and take notice.”

6. Prospect into multiple territories

What if those different departments aren’t just on different floors but in different countries?

This is common with enterprise organisations, which often have over 1k employees working in offices worldwide. All those offices may have their own budgets and control over their sales tools.

How do you navigate that? 

Simon said:

“What we do is target stakeholders in multiple territories. If you can book meetings with different people across different locations, that gives you much internal sway.”

Simon uses those stakeholders to create more openings in the company. Like this:

“We spoke with (name) in (office location). They love the tool and are adopting it. Would you like to see it?”

He went on:

“It’s about leveraging the internal networks inside those companies. If you can get your name talked about internally, then that creates a real buzz around your product. People will start coming to you for a demo!”

7. Know your competition

This can be challenging when selling enterprise software, especially if your client already uses a competitor.

For Josh, it’s all about finding your niche.

“Sometimes it’s not about replacing the competitor, but showing the client how your tool can work alongside them. Using Cognism as an example, some of our clients use LinkedIn Sales Nav in tandem with Cognism.”

“It’s okay for clients to use multiple solutions simultaneously; this is standard in many enterprise orgs. So it’s not about supplanting the competitor but highlighting what you’re better at.”

“If it’s a straight head-to-head scenario, it purely comes down to what the client is trying to solve. Are they looking to buy multiple solutions? Do they have the budget for it? That’s all you have to answer - are you a good fit for solving their problem?”

8. Keep your activity high

When selling SaaS to enterprise, not every conversation you have will be to book a meeting.

That said, don’t think you can get away with keeping your activity low. To succeed in enterprise sales, you must start as many conversations as possible.

Al said:

“Activity is essential in enterprise sales targeting. There’s so much information gathering. You must pick up the phone every hour, find out who works in which department and then call those people. You have to learn the tech they’re using and discover if they have an issue with it.”

He had some advice for keeping activity high in enterprise selling:

“Reach out to as many people as possible. It’s an obvious point, but enterprise orgs are big. The chief execs at those big companies get bombarded with pitches every day.”

“The best way to break through the noise is to create a groundswell of interest from the junior employees - which means contacting them en masse. All you need is one or two of them to respond.”

9. Book multiple meetings from one meeting

Let’s say you’ve followed our first eight tips and reached the enterprise sales Holy Grail - you’ve booked a meeting with a stakeholder!

Simon shared a great tip for maximising your chances of success:

“When you’ve booked a meeting with a decision-maker, try to bring more people from the company along with them.”

If you’ve booked a demo with the company’s Sales Director, you could approach the Heads of Marketing and RevOps with a message like this:

“I’ve got a meeting with (name) from sales next week. The tool has a perfect use case for (marketing/RevOps). Would it be worthwhile for you to hop on that call, too?”

Simon explained the reasoning:

“You use that initial meeting to open up conversations and book even more meetings. Pull in more decision-makers and align them.”

10. Give your AE as much info as possible

The final step in enterprise selling is ensuring the AE has everything they need before their demo begins.

Simon gave us a list of the key points AEs need:

  • The pain points that the company and individual decision-makers face.
  • The B2B technology that the company uses - specifically if they’re using a competitor.
  • The names of all the people signing off on the deal, including their job titles, responsibilities, and relations to each other, as on the company org chart.
  • Any legal complexities encountered that will likely become a negotiation issue.

Simon said:

“It’s up to the rep to manage this handover well. If in doubt about a piece of information, include it. You can never have too much info in enterprise sales.”

All of this said, selling enterprise software can be challenging, but it’s worth it! 

To make it easier, consider investing in a leading B2B data provider for more conversions and increased revenue👇

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