It’s time to answer this enterprise sales question:
What do you do once the SDR has passed the prospect onto the AE?
For this blog, we called upon the expertise of Josh Knipe, formerly Cognism’s Head of Enterprise Sales. During his tenure with us, his team smashed record after record - including signing Cognism’s biggest-ever deal!
Who better to ask about the art and science of closing 6-figure enterprise sales deals?
Scroll 👇 for Josh’s insights or use the menu to jump to a section.
Closing 5-figure deals vs. closing 6-figure deals: what’s the difference?
Our first question for Josh was how the B2B sales process differed between signing 15k deals and signing 200k deals.
“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 be dealing 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 be talking to people in departments like legal, procurement, IT, finance - 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 make sure you have a schedule in place and that the client agrees to it. That will help to keep you focused during a long sales cycle.”
Enterprise sales discovery: top tips
We asked Josh how he makes the most of discovery calls in enterprise sales.
“Don’t start by overwhelming your client with product features! Instead, dig into what the client’s expectations are.”
“What do they want to get from using your product? What’s important to them? Then you have to align their expectations with what you offer.”
“You can do this by asking a lot of open-ended questions. I call this ‘peeling the onion’. The prospect may say that 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 need to understand who else in the company needs to be involved in the deal.”
Josh gave us a list of questions that he likes to ask:
- What do the company’s internal processes look like?
- What other decision-makers need to be looped 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?
Cultivating internal champions
Bearing in mind that enterprise deals have multiple stakeholders involved, we asked Josh how he goes about creating internal champions.
“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 even happen.”
“It helps if you have a great B2B marketing team. We’re fortunate enough to have this at Cognism! There are lots of resources at the sales team’s disposal - so by the time I get involved, people are already clued in about Cognism and what we do.”
“My job is to then start a dialogue and discover the prospect’s pain.”
Managing multiple prospects
How does Josh navigate enterprise orgs and deal with a slew of prospects at once?
“First up, 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’ll be able to branch off into different departments or even territories of the business. It’s a multi-threaded approach; you’re prospecting to potentially dozens of people at the same time.”
“You also have to present those silos with specific use cases for your product. How sales will use a product might be very different to how marketing will use it, for example. It’s vital that you 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, then closing the deal will go a lot more smoothly.”
Managing admin
One thing that Josh impressed upon us when dealing with enterprise was the importance of staying on top of your sales admin.
“By far the most critical email is the first one you’ll write - your first follow-up email.”
Josh gave us a breakdown of what this email must accomplish:
- It must recap and define the business challenges you’ll be solving for the client.
- It must confirm an ongoing timeline for the deal to progress through.
- It must obtain written confirmation from the client that they agree to the timeline.
“As a SaaS sales rep, you never want to be working to your timeline. You want to be working to the client’s timeline. So it’s important to set expectations early on, based on their internal processes.”
“That first email is so crucial because then you’ve got a written document you can refer back to as you work on the deal. You have certain dates that things must be completed by, that both you and the client have agreed to.”
“That way, if dates start slipping and important deadlines are missed, then you can hold the client accountable. If you find yourself in that situation, you can say something like…”
“We agreed that the first round of evaluations would be completed by (date). I’m concerned that we’re behind our agreed timeline.”
“How do we adjust this so that we make sure we’re moving forward?”
“Another thing you can do to smooth the process along is to put together strategic presentations for your prospects. This is when you create bespoke decks or presentations for your internal champions to present to the decision-maker.”
“The benefits of doing this are that it saves them time and makes them act as your internal salespeople. A sales pitch is always going to be more valuable coming from someone the decision-maker knows and trusts rather than a stranger.”
How to avoid a closed-lost
In Josh’s opinion, the biggest reason for closed-lost deals in enterprise sales is no decision. He told us:
“If the timeline slips and the deal continues to get dragged out, then you’ve already lost that deal. All you’ll be doing is chasing a deal that’s never going to close.”
“The best way to overcome this is simply to stick to the timeline and keep your prospects accountable. Communication is key.”
Josh asks his prospects a question to help him set a timeline:
“Have you ever closed a deal of this size before?”
“If the answer is yes, try to understand what that deal looked like. What timeline did they follow for that deal? When you know that, then you have a framework to follow for your deal.”
“If the answer is no, then understand who else from the company needs to be involved in the deal.”
How to deal with competitors
This can be a challenge in enterprise sales, especially if your client is already using a competitor and getting value from it.
For Josh, it’s all about finding your niche. What makes your product different?
“Sometimes it’s not about replacing the competitor, but showing the client how your tool can work alongside them. Using Cognism as an example, a lot of our clients use a competitor for US data, but they use us for international data.”
“It’s okay for clients to use multiple solutions at once; in fact, this is standard in many enterprise orgs. So it’s not about supplanting the competitor but highlighting the things that you’re better at.”
“If it’s a straight head-to-head scenario, then 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 really all you have to answer - are you a good fit for solving their problem?”
How to get the client to sign
What’s the number one thing that enables Josh to close 6-figure deals?
“Enterprise deals are won or lost on whether the client sees value in your product or not. If they see the value, budget doesn’t often matter that much. You should be able to get the deal over the line because they see and understand the value in what you’re offering.”
“If they don’t see the value, then closing the deal will be an uphill battle. So you have to prove the value first and foremost.”
“This goes right back to discovery. If you don’t get it right, then you’ll have to go back and do it again - and that usually leads to the deal stalling and a ‘no’ decision.”
How your team can help close the deal
Josh is a firm believer in a team approach.
“Your SDRs and marketing team educate businesses on what you do and your value prop. Never underestimate them. They warm your clients up.”
“In an enterprise deal, when you get to the ultimate decision-makers - the CEOs, CMOs, CROs - when you reach those people, it’s more about positioning the deal as a long-term partnership, rather than just a one-off sale.”
“Showing them that there’s a whole team of people behind the deal goes a long way in terms of closing it. Why? Because it proves commitment. It shows that collectively, as a business, you’re keen to develop that long-term relationship and work alongside each other.”
4 key takeaways
Josh abides by these rules when working on 6-figure deals:
- Make sure you understand the problems that the client wants to solve.
- If you can solve their problems, then and only then is it worth starting a conversation.
- Always agree on a revenue goal and timeline and hold the client accountable for it.
- If you can’t solve the client’s problems, then it’s okay to walk away from a deal. Don’t be afraid to say no!
