If there’s anything enterprise sales is not, it’s a one-and-done deal. Supporting global organizations requires always thinking two steps ahead while maintaining potentially dueling expectations.
The following six NYC sales professionals handle the responsibility by properly aligning product-based solutions with the client’s vision and gathering feedback early and often. For example, Laura Meintel, a senior enterprise account executive at software company Neverware, asks for verbal confirmation after she references any detail she thinks might be open to misinterpretation –– with every person she speaks to on the account. She and Kristin Myros, Yext’s director of enterprise sales, both compare their roles to solving an intricate puzzle.
That said, not all puzzles require identical solutions or production timelines.
On sales calls, Myros abides by author Rob Fitzpatrick’s “mom” test. Instead of simply pushing solutions she believes might work best based on experience, she tries to get to the root of what matters to the person on the other end of the line. That way, results aren’t clouded with her ego or perceptions surrounding the software company’s product.
The complexities of enterprise sales aren’t limited to internal client structure. For transparency’s sake, Dan Thompson, VP of sales for the Americas at Peakon, said his team created a mutual action plan that details who does what and when from the time a project is approved to the time the client starts to realize value. At Peakon, that value comes in the form of quantitative employee feedback.
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?
The main difference I’ve found between selling enterprise accounts and SMBs is the number of stakeholders involved in the process. This creates additional complexity, since each individual or team may have slightly different concerns, goals and agendas. You need to be great at discovery, active listening and building consensus. You are also less likely to have direct access to the C-suite in these accounts, so identifying potential champions and helping them justify the value to the economic buyer is key to getting your solution approved and funded.
What’s different about the sales process when selling to enterprise clients?
Larger companies will generally be more concerned with de-risking the decision than their smaller counterparts and have a greater need to sell the project internally. In order to address these challenges, we’ve made it a practice to map out the various stakeholders involved in the buying process and engage them early to ensure we’ve understood all of the customer’s concerns, not just the project owner’s.
Most enterprises haven’t purchased a solution like ours before, so it’s important that we help them identify the right titles and departments to involve, rather than hoping they’ll get it right on their own. From there, it’s all about linking our capabilities to their goals and working with our champions to quantify the impact into a business case before presenting our proposal –– something that’s often overlooked when selling to SMBs.
Healthy skepticism beats optimism seven days per week.”
What’s one valuable lesson you’ve learned in enterprise sales?
Healthy skepticism beats optimism seven days per week. I’m a naturally optimistic person and a firm believer in the power of positive thinking. But it’s common for salespeople to let that optimism cloud their sense of reality. When that happens, they don’t take the actions needed to win the deal.
Whether I am working on a strategic initiative, helping out on a deal or simply coaching one of my reps, I ask these questions: Do we know this to be true or are we making assumptions? What happens if the customer does nothing? Why won’t this deal happen?
It’s also important to look at your customers’ actions to ensure they are consistent with their words. Anything else is a red flag that needs to be addressed.
At Yext, Director of Enterprise Sales Kristin Myros thinks outside of the box when it comes to client outreach. For example, her team recently secured a deal with a prospect’s CEO by tweeting out a custom video about how the cloud-based search platform could benefit their business. She understands that, especially in enterprise sales, tailored messaging goes a long way.
What skills have you found to be critical to your success as an enterprise salesperson?
I view every sale as a puzzle. I know I have a solution, but I need to understand the client to map their pain points and stand out in the process. I am obsessive about putting myself in our clients’ and prospects’ shoes. I can’t expect them to take the meeting or put their reputation on the line if I wouldn’t do the same. For example, my co-workers and I shot a video about how we could help a then-emerging company and why the company inspired us. We tweeted it to the company’s CEO and within 20 minutes, she accepted my meeting. That approach had more passion and power — and results — than anything I could have conveyed in an email.
In that vein, it pays to simplify everything. Be curious and creative from the first outreach to the final pitch deck. If it doesn’t pass the “mom” test, I need to simplify my message again.
What’s different about the sales process when selling to enterprise clients?
With enterprise clients, negotiation, procurement and contracting are detailed and complex. I have been fortunate to have coaches at Yext to help me develop in these areas.
I believe you should dedicate the same time and strategy to every client regardless of the dollar value. You never know what company could evolve to be one of your biggest partners. That said, enterprise deals require a lot of time, skill and attention to detail. You can’t leave a negotiation thinking you have won. Both sides need to leave the table feeling content and confident that the relationship will be successful.
Everyone loses deals. If you can learn why a deal didn’t go through, you can improve.”
What’s one valuable lesson you’ve learned in enterprise sales?
If I lose a deal to a competitor, I call or email my prospect and ask for feedback. What could I have done better? What were the missing pieces? If it was price, how much were we off?
Everyone loses deals. If you can learn why a deal didn’t go through, you can improve. You just need to be humble enough to ask.
Laura Meintel, a senior enterprise account executive at Neverware, credits her growth in the role with a deep understanding of people. That quality, among others, can often make the difference in closing a sale. Meintel said that she talks to a range of individuals involved at different stages of the sales process. So she makes a point of understanding everyone’s role in the project, how they work together and what they care about.
What skills have you found to be critical to your success as an enterprise salesperson?
I’m of the mindset that many of the skills that make a successful enterprise salesperson also make a successful salesperson, regardless of the deal size. There are, however, a subset of skills that you have to perfect for an enterprise sale, including collaboration, active listening, patience and resilience.
You are nothing without your team. And as the owner of the deal, you are also a project manager. You must make sure every person who touches the deal aligns with the mission. To accommodate the real demands of large organizations, you must think outside of the box and collaborate with other teams to find that solution.
I’m not competitive with my team but rather with myself. So I take all the advice I can from my team, listening to those who have more experience. I never believe that I know enough or am done learning. That’s when you’ll get in trouble.
Lastly, enterprise sales is not for the faint of heart. The key to excelling is finding the right balance of resiliency, patience and persistence. There’s a fine line between pushing too hard and not pushing hard enough. Some deals close in a month and some deals can take a year. If you try and rush something, you will end up making mistakes.
What’s different about the sales process when selling to enterprise clients?
Before entering enterprise sales at Neverware, I was in institutional equity sales. The sales process in finance was more about convincing the customer why our product was better than our competitor’s. Once they were sold on the idea, the sales cycle closed itself.
I’ve found that in enterprise sales at Neverware, our product speaks for itself. A large part of the sales process is not convincing someone why they need CloudReady but more around confidence building. Switching to a new OS is new for most people. I have to work with the customer to think about different angles, understand how doing so would affect different parts of their business, talk them through change management and ensure everyone from their organization is on the same page. Details need to be clear and concise. My value proposition must be undeniable.
Always make sure to drive home the vital information, even if it feels like you’ve explained it too many times.”
What’s one valuable lesson you learned in enterprise sales?
Always make sure to drive home the vital information, even if it feels like you’ve explained it too many times. Also, make sure you always have the decision maker’s ear. I learned early on that just because you think you and the customer have had a conversation doesn’t necessarily mean that everyone remembers that conversation the same way. Much like in any relationship, people have different perceptions. Continue to reaffirm vital information around the deal regardless of how repetitive you feel you might be.
You never want to get to the end of a deal and have an essential part of the puzzle slow things down, especially when you had thought you had discussed it. On each call with a customer, I make sure I know where the conversation can get cloudy and I ask for confirmation. On the next call, I repeat the conclusions we came to on the previous call to ensure everyone is on the same page.
At Via, Partnerships Lead Olivia Blahut has found that the key to helping partners rethink public transportation in their city is understanding that each metropolis requires different resources. Blahut and her colleagues at the rideshare company aim to provide commuters equitable access to transit where it’s needed most. Doing so means getting buy-in from people like government officials and transit authority CEOs.
What skills have you found to be critical to your success as an enterprise salesperson?
I actually didn’t have a sales background before joining Via, but my previous role as a consultant helped me foster what it takes to build meaningful, successful relationships with both established and prospective partners. As a consultant, I helped my clients develop their sales strategy, field proprietary customer research and define their long-term vision and strategic priorities. In many ways, enterprise sales at Via is really similar to consulting. It requires good listening, creative problem-solving and collaboration.
We spend months getting to know our potential partners in order to understand their needs so we can co-create innovative public transit services that will actually work for their specific communities. I think that’s the key. There’s no cookie-cutter solution that makes public transportation work in every city. We certainly provide recommendations and best practices during the sales process, but ultimately, we are successful when we combine our partners’ community knowledge and experience with our operational expertise.
What’s different about the sales process when selling to enterprise clients?
You must do your due diligence to understand the key stakeholders who need to be aware of the process from the very beginning. Because we’re often building relationships with government entities, you might need support from the mayor, the city council, the CEO of the transit agency and leaders of local community organizations, among others.
We make it a priority to ensure all involved decision-makers are informed and updated throughout the deal process. The more you research and ask questions to understand the approval process, the better equipped you are to help your partner navigate it.
It’s essential to have a genuine passion for your industry.”
What’s one valuable lesson you learned in enterprise sales?
It’s essential to have a genuine passion for your industry. Within public transportation, I’ve found people tend to care deeply about mobility and the importance it plays in equity, accessibility and sustainability.
Whether at a conference, networking event or community meeting, it’s clear when representatives from the public or private sector are excited to collaborate on solving challenges in public mobility. That excitement inspires others to think creatively as well. Cultivate that energy by staying curious about the broader industry, not just your specific company or product. It sounds simple, but constantly engaging with and learning from conferences, webinars, academic work and thought leaders is invaluable as you look to build trusting, long-term partner relationships.
While the foundation of SMB sales and enterprise sales might look alike, Comply Advantage’s Michael Orrick notes the differences between the two roles. According to the fintech SaaS company’s president of the Americas, enterprise sales require a much deeper analysis, discovery and insight process to determine clients’ multidimensional needs. And that’s just the tip of the iceberg.
What skills have you found to be critical to your success as an enterprise salesperson?
In enterprise sales, you need to be a sharper listener, do deeper analysis, have tighter success metrics and far stronger end-to-end project management abilities. Enterprise sales bring in more complexity, depth and long-term opportunity than transactional SMB sales. The role demands greater patience, higher-quality communications and negotiation skills and a strategic planning approach to multiyear, multilayer selling.
If you can meet these demands effectively and repeat this process across different business units or geographies, you can build a client for life.
What’s different about the sales process when selling to enterprise clients?
Enterprise clients typically bring forward more complex use cases, higher business values and volumes, more complex technology ecosystems and more demanding regulatory environments.
I found that I had to adjust my expectations regarding the time it would take to properly identify the right elements of procurement, data security and project decision-making. I had to open my network of influence within the client's company wider and deeper. I also put far more effort into true critical-path planning to constantly reassess and review my assumptions and ensure that my program plan aligned properly with the client. I would hit their time and budget milestones by reporting back and refining my plans on a frequent basis, even in the choppy and remote COVID-19 economy.
Never assume you know a new client’s pains and problems...”
What’s one valuable lesson you’ve learned in enterprise sales?
Every use-case is as unique as a snowflake or fingerprint. Never assume you know a new client’s pains and problems or that those pains and problems are equally reflected across their different business units and geographies. Even within the same industry or market segment, every enterprise client has a different algorithm underlying their business.
I involve pre-sales early in the sales process, work product experts in as we uncover different use cases and nuances and begin work with our customer success team on the project operations plan well before we close a sale. This approach gives our enterprise clients greater confidence in our sales process and gives us more leverage within the prospect base.
Jake Farmakis, an enterprise account executive at corporate travel company 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 familiarizing yourself with the company’s objectives, pain points and who’s who in the organization.
What skills have you found to be critical to your success as an enterprise salesperson?
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 five- or 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, multithreading 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.
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.
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.”
No matter how long you’ve been in enterprise sales, keep pushing yourself to learn from others.”
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.
