After spending eight months working with an organization, aligning on business objectives and building champions among numerous stakeholders, Chris Jennings encountered a common — yet excruciating — pain point many enterprise account executives experience in their careers: the primary executive was let go.
Fortunately, Jennings had spent ample time with stakeholders across the business, ensuring more than one person understood and valued the solution SaaS operations management platform BetterCloud was offering. He closed the deal a few weeks after the replacement was named.
The lesson? “Expect the unexpected,” Jennings said.
Enterprise sales requires polishing some different skills than SMB roles. Identifying key decision-makers across a business is just one of them.
Jake Farmakis, an enterprise account executive at corporate travel company Navan, said time management and learning how to challenge potential buyers are equally important abilities to master.
Jennings and Farmakis shared their top tips for AEs breaking into the enterprise space with Built In SF. Some themes we recognized: Do in-depth research before reaching out to clients, speak with peers and clients in the enterprise space before taking the leap, and learn how to multi-thread deals.
To Chris Jennings, a strategic account executive at BetterCloud, the sign of a productive AE is the ability to determine what’s important to the decision-makers on enterprise accounts. Doing so allows his colleagues to map their ROI in a strategic manner. As a result, enterprise clients are able to make collective decisions or defend company purchases to a board as necessary.
What skills have you found to be critical to your success as an enterprise salesperson, and how do they differ from the skills you needed to sell to smaller companies?
Many of an organization’s top-tier logos and influential accounts tend to fall in the enterprise space. Selling into these accounts requires a great deal of due diligence and planning. One of the most critical skills required to be an enterprise account executive is the ability to map out a complex account and strategically outline the course of action required to start a sales cycle.
At smaller organizations, the buying power or influence tends to be concentrated in a specific group of individuals. At enterprise companies, it can be spread across multiple different divisions, departments and figureheads. With that in mind, an enterprise AE needs to spend time identifying decision-makers, outlining a strategy for your product’s value proposition and building relationships to connect the key players in the account.
What’s different about the sales process when selling to enterprise clients?
Enterprise organizations typically have far more stakeholders involved in any one decision, which can draw out the process and the sales cycle. Get into the habit of doing research on every individual you speak with at the account. Seek to understand their role and responsibilities. Hypothesize what their goals might be for the business.
In order to adjust and refine my process, I spent a lot of time learning from my peers with experience working accounts at this scale. I also talk to former customers I had relationships with who are now working with enterprise organizations. I have been able to learn about what processes had changed in their world, the new challenges they faced and how their organizations engaged with vendors.
I also started spending a significant amount of time digging into the businesses of my accounts. I read 10-Ks, listened to earnings calls and analyzed their public announcements so I could understand what was driving their growth and the challenges they were facing.
It’s completely realistic for your primary champion or key executive to leave the organization mid-cycle.’’
What’s one really valuable lesson you’ve learned in enterprise sales?
Expect the unexpected. During a sales cycle, you can put in all the hard work to develop all the right relationships and make a strong case for your product. But it’s completely realistic for your primary champion or key executive to leave the organization mid-cycle. You have to build strong relationships across the organization to prevent your deal from hinging on one or two individuals.
For example, last year, after having spent eight months working with an organization, aligning on business objectives and value propositions and building champions across numerous stakeholders, the primary executive was let go. It appeared the deal would fall apart. Fortunately, because I had spent so much time with each stakeholder across the business and ensured everyone involved understood our solution, we closed the deal a few weeks after the replacement was named. The deal would have died without the support of champions across the business fighting for us in uncertain times.
Jake Farmakis, an enterprise account executive at Navan, does his homework before he gets on the phone with a client. Farmakis said that doing necessary research often involves being able to say “no thanks” to any items that may distract you from becoming familiar with the company’s objectives and pain points, as well as who’s who in the organization.
What skills have you found to be critical to your success as an enterprise salesperson, and how do they differ from the skills you needed to sell to smaller companies?
Time management, multi-threading and learning how to respectfully challenge the prospective buyer are some of the top skills that come to mind when I think about success in enterprise sales. I mention these three because they’re relatively obvious, yet at the same time, harder to master than you might think. Of course, anyone who strives to be successful in enterprise sales should have a great understanding of their product, their industry, their competitors and their customers.
Time management is critical. You only have a certain number of at-bats with each client. You need to ensure you’re putting in the proper amount of time before each call to research the account and understand their business model, their latest earnings reports and company priorities. That doesn’t happen in a 10-minute cram session. Given the complexity of each account and the number of stakeholders you’re likely going to meet, this is especially true for enterprise sales. Think about how many other vendors enterprises speak to throughout the day. You need to do the work prior to your meeting so you can tailor the conversation and differentiate yourself from the pack.
I map out each account, multi-threading to more than one stakeholder so I can keep deals moving forward when one or two contacts go dark. By leading to your solution as opposed to leading with your solution, you’ll notice a major difference in the way prospects respond to your consultative approach.
You only have a certain number of at-bats with each client.’’
What’s different about the sales process when selling to enterprise clients?
It goes without saying that enterprises often move through the buyer journey slower than smaller-sized businesses. It’s typical to have a great intro call only to get led down the path of multiple stakeholder meetings that result in misaligned priorities. The worst thing you can do is set yourself up for a “slow no” by starting with a lower-level stakeholder and hoping that he or she will fight for your solution internally. Over the years I’ve learned this lesson the hard way. I have had to adjust my approach.
I start by making sure I research each account before I begin outreach. Instead of targeting any enterprise that has sizable travel volume, I’m specifically looking at company size, demographic, geographical footprint, industry (maybe we have one of their biggest competitors as a customer?) and personal connections via LinkedIn Sales Navigator. That way, I can leverage multiple touchpoints once I’ve determined a great fit.
I also make a conscious effort to ensure the C-suite is involved as early as possible. This is harder than it sounds, but account-based outreach and targeted messaging will make a difference, especially if you get senior stakeholders engaged early on. After the intro meeting, say something like, “Typically when we engage with a customer for this sort of solution, we need certain key stakeholders to be involved in the purchasing decision. Is that the case here?”
If the customer says “yes,” ask them if you’ll be able to meet with those executives. If the customer is unsure, push back and say something like, “If you can’t guarantee time with key leaders, we’ll be unable to check if everyone is aligned on the value of our solution. Therefore, it doesn’t make sense to continue engaging in further discussions.”
What’s one really valuable lesson you’ve learned in enterprise sales?
No matter how long you’ve been in enterprise sales, keep pushing yourself to learn from others. Don’t get stale or complacent. I’ve become obsessed with podcasts and blogs from thought leaders like David Priemer, John Barrows and Scott Ingram. They include “Cerebral Selling,” “Make It Happen” and “Sales Success Stories,” respectively. And if you need a motivational boost, just watch one Gary Vaynerchuk video on YouTube and you’ll be set.
I’ve also made focusing on my mental health these last few years a habit. If you spend time focusing on healthy eating, quality sleep, meditating daily and exercising as much as possible, it will pay off when dealing with the inevitable stress that comes with enterprise sales.
