Guiding Sales Reps Into the Depths of Enterprise Sales

In a sea of competition, selling to large organizations can be an intimidating proposition.
Written by Jeff Kirshman
March 8, 2022Updated: March 8, 2022

If you’re going to go fishing, you might as well catch a lot of fish. But why stop there? Why settle for minnows when you can reel in a largemouth bass?  

The answer, of course, is that bigger fish are harder to catch. Simply casting a wide net isn’t enough. Bigger fish require a more spirited fight, with a wide assortment of lures and bait to hook them in. 

The same goes for sales reps looking to leave the shallow waters of midsize clients for the depths of their enterprise counterparts. Enterprise sales, like deep-sea fishing, has more moving parts and requires high involvement from both buyers and sellers. Send an unprepared sales rep into choppy waters, and they risk getting lost at sea. 

“It all comes down to fundamentals,” said Chris Dinkler, chief revenue officer at fintech company Enverus. “If you know how to communicate value, ask the right questions, build rapport and position your products and services to the buyer’s needs, you’re never out of your league.”  

As Built In Colorado learned through conversations with four local sales leaders, there’s no reason to be intimidated by the prospect of pursuing enterprise clients. Sometimes it’s just a matter of adjusting your technique to hook a big one.

 

Trisha Loy
RVP, Enterprise Sales

 

What are the biggest differences a rep used to working with small and mid-sized businesses will experience when selling to enterprise organizations for the first time?

Enterprise sales ventures have more decision-makers, influencers and key players who will determine and set the project timeline and pricing. C-level executives may directly or indirectly be involved in your project, and this opportunity will help strengthen executive presence and collaboration. Some projects can feel lengthy, so it’s important to understand whether the project has been budgeted or scoped in order to accurately forecast and move the project forward. In the enterprise space, it’s not all about pricing; understanding a company’s financials, return on investment, total cost of ownership , and private or public trading status are all key components. Doing your research goes a long way.

Lastly, there are typically fewer — yet larger — accounts to call on. Your messaging must be targeted, but also personal. It’s important to maintain human connection, even with larger orgs. Along with consistent networking, establishing personal connections is important not only to nurture the business relationship, but also to get a warm introduction to others in the organization.

It’s important to maintain human connection.”

 

How can managers prepare sales reps to handle those differences?

In today’s age, virtual presence matters. To prepare for the transition into enterprise, practice makes perfect. Practice your messaging, as well as your video presentations. Anticipate questions ahead of time and practice your responses to keep prospects engaged. Managers can not only help prepare sales representatives to handle these differences, but also to empower them to be successful through learning and practice. 

At RingCentral, a key pillar in our training is “selling through curiosity.” It’s important to ask questions that dive deeper into a customer’s needs, goals and pain points in order to solve problems and be successful. 

Another way sales managers can help reps prepare is to establish personas for each client. This way, reps are able to outline targeted messaging to help lead conversations in a meaningful way. Lastly, it’s important for managers to continue to empower and support sales reps when entering any transition, empowering them to lead conversations and offer guidance when needed. 

 

How do you know when a sales rep is ready to start selling to enterprise clients?

As sales reps continue to grow, their financial literacy and knowledge will expand as well. Understanding the uses and meaning of general terminology like capital expenditure, operational expense, amortizing, deferring capital and cash flow can be a factor in readiness. Understanding the prospects’ financial situation and position in the company life cycle are also important. Additionally, presenting well in role play with managers, directors and internal C-level executives is a good indicator of when reps are ready. 

As a sales rep builds and nourishes their career, they’ll also begin to build their network. Taking the time to identify specific personas and verticals they will be selling into and creating meaningful relationships and rapport with their connections are all important. 

 

 

Scaled Agile office
Scaled Agile

 

TiNilya Thomas-Scott
Director, Sales Operations

 

What are the biggest differences a rep used to working with small and mid-sized businesses will experience when selling to enterprise organizations for the first time?

As a result of their size, enterprise organizations are more complex, they have more decision-makers and their sales cycle is usually longer. Sales representatives must also get energy from and be competent at planning and collaborating with others internally and externally. Finally, a characteristic that is often overlooked is the importance of relationship-building. Having more decision-makers dictates that an enterprise sales representative must spend a lot of time developing relationships with multiple buyers within the same organization.

 

How can managers prepare sales reps to handle those differences?

Sales managers at Scaled Agile focus on both selling skills and soft skills. In my experience, most sales representatives walk in the door with the traditional selling skills typically derived from experience and attending selling programs such as the Miller Heiman or Challenger Sales methodologies. Evaluating and ensuring that sales reps have those intangibles, the soft skills, is often overlooked. They include the ability to listen, the ability to interpret nonverbal communication, patience, and the ability to identify and respond to red, green and yellow flags. Sales shadowing, role-playing and a sound enablement program can prepare the sales rep to handle the differences associated with selling to an enterprise organization.

Evaluating and ensuring that sales reps have those intangibles, the soft skills, is often overlooked.”

 

How do you know when a sales rep is ready to start selling to enterprise clients?

Selling in general is both an art and a science. You know your sales rep is ready to start selling to enterprise clients after they have completed your sales-specific onboarding and enablement programs, have demonstrated the ability to develop an account plan based on internal best practices and can present it internally. They’ve demonstrated their mastery of soft skills through shadowing and role-playing. If they’ve checked all of those boxes, they are ready, but they also need to keep learning out in the field. We’ve found that a great enterprise sales executive is always learning about their prospects and clients. The sales relationship is fluid and responsive and allows us to collaborate on what we might achieve alongside our client.

 

 

Chris Dinkler
Chief Revenue Officer

 

What are the biggest differences a rep used to working with small and mid-sized businesses 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 as with small and medium-sized businesses, there will be instances where the buyer has already done their homework and made their decision, and other cases in which you have a totally cold lead that you have to warm up. 

However, things differ greatly at an enterprise level with the number of buyers and groups involved in the purchasing decision, which will require a more complex enterprise selling motion. It no longer becomes a single decision-maker, but several. The bigger the sale, the more that sale infiltrates the organization, likely aligning to a corporate strategy or a material challenge they are trying to solve — thus more people will likely be involved. 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 return on investment for the customer.

It no longer becomes a single decision-maker, but several.”

 

How can managers prepare sales reps to handle those differences?

A key aspect for us is having a standard sales methodology, or playbook, 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 to 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 depending on the segments they are pursuing and the types of opportunities they are pursuing, from the more transactional to selling to an installed base to more innovative, green field segments. At Enverus, we empower our leaders to own their team’s culture while embracing our standard sales playbook and keeping to our core value of #oneteam. It’s reinforcing the positives and the strengths while also providing hands-on coaching and job aids in the areas where salespeople might need them most.

 

How do you know when a sales rep is ready to start selling to enterprise clients?

In the end, it’s all about mindset. If the sales professional has the intangibles to adapt to different circumstances, ability to think critically through complex situations, flexibility to be coachable by peers and leaders, and grit and self-motivation to persevere, they will be successful no matter the type of sale.

 

 

Becky Howard
Vice President, Operations

 

What are the biggest differences a rep used to working with small and mid-sized businesses will experience when selling to enterprise organizations for the first time?

There is a larger group of decision-makers, the purchase process is usually defined and you may need signoff from three or more executives. This could result in needing multiple demos, meetings and contract discussions. We use a high-touch approach at Documoto and require multiple sales calls to gain an agreement to purchase, and the process can take months. But the size of the contract makes it a worthwhile investment.

The size of the contract makes it a worthwhile investment.”

 

How can managers prepare sales reps to handle those differences?

Sales managers can educate reps to understand how to work with complex organizations, including getting multiple key stakeholders involved in the process as soon as possible and ensuring that their presentation skills are more polished and targeted to the buyer’s business. They will need to understand that an enterprise sale is a long-term project and commit to staying with the customer and engaging them throughout the process.

 

How do you know when a sales rep is ready to start selling to enterprise clients?

When they have started to understand that they will need to involve more than one decision-maker in the process. In addition, their presentation skills have become polished, and they are comfortable speaking with every level of stakeholder, whether it is a team member, manager, director or executive. They will also need to understand how to empathize with the prospect and convey that they understand their pain points.

 

Jobs from companies in this blog

Colorado startup guides

LOCAL GUIDE
Best Companies to Work for in Denver & Boulder
LOCAL GUIDE
Coolest Tech Offices in Denver & Colorado Tech
LOCAL GUIDE
Best Perks at Colorado Tech Companies
LOCAL GUIDE
Women in Colorado Tech