Every enterprise sales rep remembers the first big account they closed. While securing any deal is exciting, there’s nothing quite like seeing weeks of hard work pay off in the form of a shiny new contract with a household name.
But that feeling of excitement isn’t just tied to one impressive deal: It’s directly tied to how some reps grow their careers and serves as a testament to all the new skills and tactics they had to learn in order to win deals with large, industry leaders.
After all, for many small-to-midsize business reps, stepping into an enterprise role is a natural next step on climbing the career ladder. But getting there isn’t always easy. After all, even nailing down the correct point of contact can be difficult, let alone navigating the complex contracts and intimidating demos that follow that first warm lead.
And while reps can do a lot to prove they’re up for the challenge, they’ll likely need support from their managers to prepare for the world of enterprise account management. To find out how managers can best help their teams level up and successfully tackle large accounts, Built In connected with two tenured sales leaders. They outlined their best strategies for identifying when talent is ready to make the jump — and how to ensure they succeed.
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
There are three differences that stand out when it comes to making this transition. First is the expansion in the size of the buying committee that reps must navigate when trying to sell to an enterprise organization. They will still be able to leverage their champion, but they must spend a lot more time mapping the organization to understand who will be involved in the sales process and who will be influencing the buying decision.
Second, there’s the length of the sales cycle. With more people involved in the buying decision, and a more complex tech stack to navigate, the time from opportunity creation to close is going to be at least 50 percent longer than reps would have experienced before. Finally, we have seen team selling become highly effective in SMB. It is absolutely critical when selling to a large organization that the sales rep partners closely with internal teams, such as solutions consulting and leadership, to build the strongest case possible as to why that company should purchase our software.
It is critical when selling to a large organization that the sales rep partners closely with internal teams.”
How can sales managers prepare sales reps to handle those differences?
The best thing a sales manager can do is to develop a training path for reps three months in advance of their transition into the enterprise segment. Making a late transition for a rep doesn’t set them up for success, so we try to avoid that.
Key components of a rep’s training path can include assigning them an enterprise sales rep as a partner (what we call a RollMate); having reps shadow at least three deal cycles and creating a call library for them to digest important calls; and allowing reps to work one to two accounts in the enterprise segment ahead of the transition so they can learn on the job.
How do you know when a sales rep is ready to start selling to enterprise clients?
When assessing if a sales rep is ready to sell to enterprise clients, I look closely at their current and past performance. Specifically, I am looking to see examples of complex organizations they have sold to, how their average deal size is trending and if it is above average in the growth segment, and what the package type is and length they have been selling to their largest opportunities. These three things give us a strong indication that a sales rep can be effective in working with larger enterprise organizations.
What are the biggest differences that a growth or SMB sales representative will experience when selling to enterprise organizations for the first time?
When selling to enterprise organizations for the first time, the biggest difference that a growth or SMB sales representative will experience is understanding and identifying the hierarchy of the right persona titles.
Given the difference in size and scale of enterprise organizations versus the SMB space, it is critical to understand the right roles and personas, and plan accordingly. For example, in the past, reps may sell to one to two people. Now, it may be an entire buying committee of people. Representatives must also have a solid co-selling, upselling and nurturing plan since organizations have multiple segments, each with unique needs.
Because this role typically involves working on high-profile contracts, reps need in-depth subject expertise.”
How can sales managers prepare sales reps to handle those differences?
Sales managers can prepare reps by providing guidance, offering training and mentorship, partaking in goal-setting, creating a sales plan, assigning sales territories and empowering the team. It’s imperative that sales managers prepare their reps for enterprise segments by explaining the major differences and helping their reps use the knowledge of the enterprise category to their advantage.
A manager can also implement transitional training with other enterprise reps who are open to sharing their shared experience of going from SMB to enterprise.
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 once they have comfortably mastered their SMB market share and start showing eagerness and passion to grow and sell to enterprise segments. Excellent sales skills, along with strong business acumen, are what make a successful enterprise sales representative. Additionally, because this role typically involves working on high-profile contracts, reps need in-depth subject expertise, as well as an ability to work under pressure.
