The oft-quoted American businessman Arnold Glasow once said, “The key to everything is patience. You get the chicken by hatching the egg, not by smashing it.”
To make sure sales reps are ready for enterprise clients, Austin tech companies can take a page from Glasow’s book. Success with enterprise clients isn’t so much about discovering brand-new skills as it is about adjusting attitudes and expectations — as well as watching the client for important patterns and responding accordingly.
“These deals take time,” said Apty VP of Sales Randy Bernard. “Patience is key, along with learning the process set forth by the buyer and optimizing for any compelling events along the way.”
Some of the skills necessary to sell to an enterprise company are the same as what’s needed for smaller ones: Reps need to understand and communicate the value of their product, build rapport with their points of contact and roll with whatever the client throws at them. The differences come in the form of scale and stakes — with an organization that big, there are significantly more steps between the start and finish line. Patience, diligence and listening skills — along with decisive action at the right time — become more important than ever.
It’s up to sales managers to make sure that their representatives are ready before sending them on the daunting task of selling to enterprise clients. Luckily, sales managers from several local companies have tips for preparing sales teams. Built In Austin sat down with leaders from Enverus, Adia, inKind, Shipwell and Apty to learn how the reps in their care succeed at selling to these large companies — and how they level up their process and patience to get these valuable eggs to hatch.
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
No matter what you’re selling, the customer’s buying journey will be fairly consistent. Just like in SMB, in some instances the buyer may have already done their homework and made their decision — and in other cases it’s a totally cold lead that you have to warm up. However, things differ greatly at an enterprise level with the number of buyers and buying groups involved in the purchasing decision, which will require a more complex enterprise selling motion. The bigger the sale, the more that sale infiltrates the organization and aligns to a corporate strategy or a material challenge they are trying to solve. Thus, more people will likely be involved, and more departments and personas lead to managing competing priorities and opinions. It’s a great puzzle and it’s a lot of fun to try and solve each individual’s problems to give the entire account a comprehensive solution that matches everyone’s needs with a compelling value-exchange (ROI) for the customer.
How can sales managers prepare sales reps to handle those differences?
A key aspect for us is having a standard sales methodology that managers can use with their teams to align the sales process to the customer’s buying journey. While having this set of standards is key in building a scalable organization, it is also important to give our sales leaders the ability to set the tone for the teams they lead. Each group will have a slightly different culture than another depending on the segments they are pursuing — if it is more transactional, enterprise, selling into an install base or pursuing more greenfield. At Enverus, we really empower our leaders to own their team’s culture while embracing our standard sales playbook and keeping to our core value of #Oneteam. The trick is reinforcing the positives and the strengths and providing hands-on coaching and job aids in the areas someone might need them the most.
If you know how to communicate value, ask the right questions, build rapport and position your products and services to what the buyer needs, you’re never out of your league.”
How do you know when a sales rep is ready to start selling to enterprise clients?
This is really a question about the fundamentals and falling back on foundational sales skills, while also recognizing their ability to handle a more complex customer buying journey that includes multiple stakeholders. If you know how to communicate value, ask the right questions, build rapport and position your products and services to what the buyer needs, you’re never out of your league.
In the end though, it’s all about mindset. If the sales professional has the intangibles to adapt to different circumstances, critically think through complex situations, be coachable by peers and leaders and have the grit and self-motivation to persevere, they’ll be successful no matter the type of sale.
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
The amount of time it takes to close a deal with an enterprise organization is one of the biggest differences a sales rep will experience. When closing a deal with a small- to medium-size business, you typically will need buy-in from one, maybe two people. Due to this, a deal can be closed the same week. When dealing with an enterprise client, you will need buy-in from multiple departments and different levels of seniority within those departments. This can take anywhere from a month to over a year.
How can sales managers prepare sales reps to handle those differences?
Helping sales reps understand that having patience will be their key to success is crucial. No one wants to be forced to buy anything they don’t need, so being pushy or impatient can often lead to a client losing trust. When a client feels like their space and time is being respected, you are more likely to get the deal.
When a client feels like their space and time is being respected, you are more likely to get the deal.”
How do you know when a sales rep is ready to start selling to enterprise clients?
A sales rep is ready to start selling to enterprise clients when they can clearly and methodically navigate through a large company, find the initial point of contact, build a relationship with them and get additional meetings with other departments within the company. This sales rep should be equipped to handle questions outside of what is being sold — think purchase orders, finance, accounting and reporting. If this sales rep can do all of this on their own, they are ready for the big lights!
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
The most significant differences tend to center around the expectation and customization needed to appease an enterprise organization and the increased stakeholder buy-in necessary to close any deal.
While it is challenging to master, an enterprise sales representative must find the balance between customizing their product to specific enterprise needs while not over-promising anything that is neither possible nor scalable. Enterprise organizations will expect a more tailored product fit than any SMB organization, which increases the risk of sales representatives over-promising and under-delivering.
Additionally, while an SMB or growth sales representative may also be comfortable selling to one or two decision-makers, most enterprise organizations require sign-off from numerous executives before moving forward. As a result, enterprise sales mean not only a much longer sales cycle but also a need to tailor any pitch to target the needs and pain points of each stakeholder.
How can sales managers prepare sales reps to handle those differences?
There is a common misconception in enterprise sales that to be successful, each sales representative must have complete mastery of each facet of the business they are trying to sell. While it is imperative to know your product well, sales managers can improve the knowledge base of their sales force by encouraging team members to converse with members of other departments. This will save time and money in training by teaching their sales representatives to bring other key team members into the conversation when necessary and appropriate to sell to enterprise organizations.
It isn’t essential to know everything — instead, it is more important to know who knows everything and who to include in the conversation. It is imperative to have a sales force that understands when the marketing, tech or product team may add value. Naturally, by bringing in the most knowledgeable team members, the sales representatives will then learn more themselves, teaching them every nuance without slowing down enterprise sales.
It is vital to have confidence that any sales rep selling on the enterprise side is a positive reflection of your brand.”
How do you know when a sales rep is ready to start selling to enterprise clients?
There is substantial reputation risk when selling to enterprise organizations, so it is vital to have confidence that any sales rep selling on the enterprise side is a positive reflection of your brand. While mistakes can be made that will not have more significant brand implications on the SMB side, a failed sale or a negative reflection of your company from an enterprise client can have substantial consequences. Thus, the first question is whether this representative demonstrates the type of customer service and skill necessary to show that inKind is a dependable and trustworthy organization.
Another metric I consider when evaluating if sales reps are ready for enterprise sales is their ability to distinguish themselves through the timeliness of their sales cycles. As the enterprise sales cycle can be substantially longer than that of an SMB, any efficiencies or inefficiencies that sales reps may have in their processes are accentuated. While patience and perseverance are two essential qualities that a sales rep must have on the enterprise side, it has to be coupled with an urgency to close the deal and the ability to capitalize on momentum whenever possible.
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
What I typically see in supply chain and logistics sales is that the primary contact for the enterprise organization has more experience and understanding of the industry than someone who has been in smaller organizations. Many times, the people running a large enterprise customer’s highly complex supply chains have been in the industry for quite a few years and have seen multiple transportation cycles. The sales rep needs to be prepared to have a different level conversation with these enterprise organization contacts.
How can sales managers prepare sales reps to handle those differences?
Outline the issues that enterprise customers could be seeing on a daily basis, then discuss with the sales reps what those issues mean to their business and how we are able to help address and mitigate said issues. From there, sales managers should be on calls and meetings with sales reps to show them how these conversations can play out and how to navigate the expectations of enterprise companies.
Outline the issues that enterprise customers could be seeing on a daily basis, then discuss with the sales reps how we are able to help address and mitigate said issues.”
How do you know when a sales rep is ready to start selling to enterprise clients?
Typically I’ll know a sales rep is ready for enterprise customers after their close ratio of smaller customers rises dramatically. They will also have moved away from needing assistance on meetings for the smaller accounts and able to close them independently. You also know when a sales rep is ready when they look to get a better understanding of the industry by reading market trends and sharing out to the team.
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
The core concepts of selling into the enterprise are not that different from mid-market or SMB in the sense that you still have to uncover pain, prove value, build relationships and be liked, knowledgeable and available — typical standard things that it takes to communicate with people and sell.
The big differences are that you are typically working in a much longer sales cycle driven by the process set forth by the organization who is buying — which means that those relationships have to stand the test of time. Additionally, you are typically selling to a broader set of personalities and titles in the enterprise.
With different titles comes different interests and evaluation criteria, which means that sellers need to help prospects understand how the product benefits the users and provides value back to the organization — in the form of true ROI — rather than understanding it just from a feature and functionality perspective.
How can sales managers prepare sales reps to handle those differences?
One of the most important ways to prepare reps is to help them understand all of the different personas they will encounter. Across the enterprise, there are many different people who solve very different challenges and care about very different things. For instance, there are some people reps work with during the sales cycle that care about how easy the product is to use and what features come with it, whereas others only care about technical specifications or ROI. Getting your salespeople exposure to all of these personalities can help your reps deliver value to each and every one.
Sales managers also need to teach newer sales reps how to gain access to others on the buying committee. Too many salespeople have only one champion during the sales cycle. Many times, that person does not have access to the budget or the decision-maker — which will eventually stop you dead in your tracks. Learn to multi-thread.
Salespeople have to win some and lose some before they can manage the entire sales cycle front to back.”
How do you know when a sales rep is ready to start selling to enterprise clients?
Most large enterprise deals are lost two or three times before they are won. Maturity, attitude, work ethic, organization, persistence and experience all prepare a sales rep for selling into the enterprise. Salespeople have to win some and lose some before they can manage the entire sales cycle front to back so that they can learn the art of staying close — but not too close — to the prospect along the way.
Patience is key. Enterprise selling has many ups and downs, and you rarely talk to the true decision maker until very late in the process. Individuals that have held roles as sales or business development representatives can help, since they’ve learned the art of prospecting, qualifying and holding people accountable. Also, those that have closed-won a dozen or more smaller transactional deals at smaller price points with shorter sales cycles will be really prepared for the long and bumpy road that is selling to the enterprise.
