Building an Enterprise Sales Strategy: Tips From Experts

Longer cycles, more stakeholders, more complications. These are just some things that make enterprise sales different.

Written by Brian Nordli
Building an Enterprise Sales Strategy: Tips From Experts
Image: Shutterstock
Jessica Powers | Aug 31, 2022

When it comes to enterprise sales, chief sales officer Cameron Orr has a mantra that his team rallies around when things are looking bleak.

“You have to get through two ‘No’s’ on every deal before it will close.”

That’s because no enterprise sale is without its snags. With sales cycles that can last anywhere from three months to more than a year, anything can happen to derail the sale. A key stakeholder may leave the company, a new CEO may have other budget plans or a pandemic might disrupt everyone’s lives.

Enterprise Sales Definition

Enterprise sales, also known as complex sales, usually refers to selling to large companies. Sales can also become enterprise sales when a product has a big enough impact, when there is a multi-year contract or complex implementation and risk.

Still, there are ways to find stability in marathon-length sales cycles. It starts with a detailed sales process and transparent conversations with the customer.

Enterprise Sales Tips From the Pros

  • Develop a detailed sales process. Without one, it can be difficult to make changes if your team isn’t hitting its numbers.
  • Identify a champion within a company and work with them to find more. Every sale needs at least three champions to push the deal across the finish line. 
  • Create a mutual action plan and share it with stakeholders. Having a detailed action plan helps build trust with the buyer.
  • Expect to hear “No” at least two times. It’s the enterprise seller’s job to find creative ways to solve for hesitations and make a deal.
  • Communicate with the customer — a lot. Enterprise sales is a marathon, so taking the time to check in with the customer regularly can go a long way in getting a deal done.  


Enterprise Sales Strategies From Experts

To learn more about how to get a foot in the door with enterprise companies and how to close an enterprise sales deal, we spoke with four experts, whose responses have been edited for length and clarity:


Enterprise Sales Leadership

What Does an Enterprise Sales Leader Need to Establish an Effective Enterprise Sales Strategy?


Brady: It’s going to sound funny, but the first step is to actually have a strategy. A lot of people think that because enterprise sellers have a lot of experience, you can just let them do their own thing and they’ll close the business. That’s how you wind up with a lot of tribal knowledge, and it becomes very hard to identify what’s broken. If you don’t have a set sales process, you wind up with a problem that you have to fix one individual at a time, versus making a tweak to help the entire sales team. Just because you have enterprise sellers, that doesn’t mean the process goes out the window. In fact, it’s more important than anything.



Tribble: One thing we did was narrow down our prospect list to the top 100 accounts that match our ideal customer profile perfectly. Those are the top 100 accounts that we would want to bring in this calendar year. Then we made sure that those were all divided equally among sales team members so that we have that covered perfectly. This helps us prevent a situation where you might find that a rep has 17 of those ideal customers in their patch of accounts and someone else only has three.



Hedley: It’s very important to have a structured process that everybody knows and that the role and responsibilities at each stage are specific. We’ve developed three pipelines — the lead generation pipeline, the nurture pipeline for customers on hold and the active pipeline. Within the active pipeline, we have six stages that the sales rep needs to go through with the customer, including prospecting, discovery, due diligence (which includes demos and case studies), decision pending, negotiation and then close. It’s a fluid process, and if a customer stays in one stage for more than 90 days, we’ll move them back. The process needs to be your back-pocket book that you live and breathe by to create accountability and forecast needs.

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Enterprise Sales Tips for New Teams

How Can New Enterprise Sales Teams Work With Larger Companies?


Orr: We have a land-and-expand enterprise strategy. So we’ll use LinkedIn to figure out whether anyone in our organization has connections within a company and leverage those. We’ll also have a rep call into the sales department of a company and talk to their inbound team about their sales process and challenges. Lots of times, reps at the non-management level are very open to telling a prospective vendor where they’re having challenges, and that’s really helpful to us. We can use that information to engage the decision-maker and have a conversation that is specific to their situation.

Tribble: The first thing that you need to work on is having solid case studies. We have incredible customer advocacy, folks who are not only willing to talk about their results with PathFactory, but who also offer to do reference calls. That’s the most powerful asset that we have working for us. It’s imperative to getting your foot in the door that you’re able to say to a company like Microsoft, “Here’s what I’m doing at IBM, and here are the core stats and results,” with a quote from the CMO. Microsoft will be far more willing to take that meeting.

Hedley: We’ve hosted virtual roundtables with companies. These roundtables aren’t about UrbanBound, but what’s happening in the relocation arena. We have prospects send us questions, and then we’ll ask those questions to the roundtable. Then we have a writer who takes notes and develops 10 key takeaways, which we’ll send to prospects in the nurture stage. What that does is give us content that is directly relevant to our ideal customer profile because it’s coming from them. It’s helped us increase our number of quality meetings because companies know we’re on point with what’s happening in the industry.

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Identifying Champions in Enterprise Sales

How Do Enterprise Sales Teams Identify Champions to Support a Product?

Brady: In SMB sales, you can usually find one champion who can evangelize your product to the buyer and that’s enough. In enterprise sales, a sales rep needs to find, at minimum, champions in three lines of business. So I’ll want to build a relationship with someone in marketing, sales and customer support, so they can go to leadership and explain how the product impacts multiple aspects of the business.

It can be difficult to navigate those relationships in larger enterprise firms, but one way to do it is to establish a strategic relationship with your first champion. Ask them who they think needs to be involved to push a deal across the finish line. The more buyers and teams are involved in the buying process, the more likely you will be to get a deal done. And because more teams are committed to the product, it can be easier to get the buy-in for renewal.

Orr: The discovery process is so important. You need to have a lot of curiosity and interest around how the organization works, what tools are currently in place, what are the company’s challenges and who are all the stakeholders. In SaaS, the discovery process gets shortened because there’s such a focus on a quick sales cycle. We really dig in on qualification and discovery to identify sponsors. Mapping is also really helpful to figure out the different areas where you can provide value, and who you need to talk to on those teams.

Hedley: We start with finding one champion at the company and partnering with them throughout the whole process. We’ll stay with that individual and ask them to find out who the decision-makers are. They have to internally pitch us to that decision-maker or buying group, so we try to set them up for success by making sure we give them the materials and coaching they need to succeed. Our goal is to make that champion look like a superstar. Then we always loop that champion in at every step in the process.


Establishing Trust in Enterprise Sales 

How Do Enterprise Sales Teams Establish Trust With Stakeholders?

Tribble: Have a mutual action plan. The mutual action plan is my biggest labor of love. Buying marketing technology, or any software, is often a risk for enterprise companies. A buyer needs to be certain that this is the right platform for them, and that they can trust the salesperson. The mutual action plan is all about tracking and showing the customer what has been completed at every point in the process. It says that you’ve completed the discovery calls, you’ve gone through use-cases, you’ve done team demos and they’ve spoken to references and completed an infosecurity check. It’s something you share with the customer and refer back to at each stage of the process.

You’re building trust because you’re not just selling them a product to fill quota, but an entire plan of how you’re going to help them achieve their goals with your technology. By the time you get to the end of it, it’s not only a contract signature, but a plan for the first year of business.

Hedley: It’s important to establish that trust in your early meetings. Once you’ve done the entire needs assessment, you need to have a candid conversation with all of the stakeholders so you agree what the next steps are and what the due dates look like. Then at any time during the process where we veer off and the deal isn’t a priority, we both agree to put everything on the table so we know where each other stands. When you state those facts upfront, it becomes a partnership rather than a sales group selling to buyers. 

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Enterprise Sales Cycle Tips

What Are the Challenges With Enterprise Sales Cycles?

Brady: Snags happen all over the place, but the most likely problem is that there was not enough value shown to spend the budget. Most of the time, if you hear, “No budget,” that means you haven’t proven enough value. Early on in the conversation, make sure that you have the appropriate decision-makers in the room and go back to the basics of budget, authority, needs and timelines. If you don’t, you can make it all the way to the end of the sales cycle only to find out that they have a procurement team that will want to renegotiate the entire deal, wasting three months of work.

Tribble: During infosecurity review, if you are unclear about how you integrate to their systems and data privacy, it can cause a snag. You need to be upfront with your buying committee and share documentation with them on your compliance and integrations. Having a one-pager with that information prepared for the buyer’s infosec team is a good best practice to have. You can also hit a snag if you have a weak compelling event or a squishy value statement. You will never sell to an enterprise company if the reason is, “Jane wants our offering,” and you don’t have a back-up on why she wants it, or what ROI it will bring her team and the company as a whole.

Orr: Speaking very recently, COVID-19 is certainly an issue that’s causes lots of companies to pause purchasing decisions on new technology. So we’ve kind of prioritized industries and verticals where there’s been a neutral or even positive budgetary effect due to COVID-19, which has helped us navigate those situations. But when there is a snag, we continue to engage with the customer, and, lots of times, those delays aren’t very long. Finding ways to continue to add value and be engaged with the customer instead of checking back in in six months is so important. Be supportive and keep talking with those customers so that when those budgets come up, we can show them how we can help them save money or be more productive.

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Tips for Long Sales Cycles

How Do Enterprise Sales Mitigate Risks that Happen During Long Sales Cycles?

​Brady: There’s a lot of risk in enterprise sales to that happening. The first thing is to understand what a customer’s typical timeline is for making a purchasing decision. If the company can be honest and say, “It’s going to take us at least six months to get it through,” then you can build your sales process to span that amount of time or keep in touch so that the prospect doesn’t get cold. So asking for that timeline is really important.

All that being said, sometimes you can do everything perfectly, and the deal still drags on. People go on maternity leave or they go on vacation or they switch jobs and things just start to happen. The only thing that you can do is ask permission to be persistent. If you start to see things are dragging, you can check in and remind them that they had said this issue is a priority and that they wanted to solve it with you. Then you can ask if there are any questions you need to go over, and ask them for permission to follow up a little more aggressively and get the deal done, since you both recognized it is a priority.

​Orr: We go into every opportunity with the expectation that the customer is going to tell you flat out, “No,” at least twice before they say “Yes.” The “No” is not the end of the process, and a lot of times it’s the start. As a team, we’ll get together and strategize on how to overcome it. So we have a positive association internally with hearing “No,” and that mindset helps keep our team resilient and navigate those scenarios. That’s more important than ever during COVID-19, but it’s always helpful in an enterprise sales setting.

​Hedley: Enterprise sales is the toughest sale. An average enterprise sale can take seven months to a year and a half. It’s a marathon. What makes a difference is when a salesperson over-communicates with a customer and has a rhythm with the prospect where they agree on next steps after every meeting. If your decision-maker is furloughed for three months, you continue to communicate with them. Have a three-week check-in and send them a Dunkin’ Donuts gift card, or message them about the Cubs game if they’re a baseball fan.

Every salesperson knows these things, but I’d say that 80 percent of salespeople will tell a customer, “See you in three months,” and not check in. The other 20 percent are hustling and keeping in touch with all of their customers throughout the lengthy process. That’s how you can build a relationship and gain a lot of momentum to get a deal across the finish line.

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