The Art and the Science of Selling into Large Enterprise Accounts
Many startup companies initially set their sights on the lucrative market of large enterprises, envisioning substantial revenue opportunities and industry recognition. However, this transition from serving small to mid-sized businesses to landing enterprise-level deals can be fraught with challenges and pitfalls for the Chief Revenue Officer (CRO).
The allure of enterprise sales is undeniable, but it comes with a complex landscape of decision-makers, longer sales cycles, demanding procurement processes, and heightened competition. Successfully navigating this transition requires a nuanced approach, strategic adaptability, and a keen understanding of enterprise customers' unique demands and expectations. In this endeavor, the CRO plays a pivotal role in orchestrating sales strategies that can unlock these high-value accounts' potential and mitigate the risks associated with enterprise sales.
After speaking with several CROs and heads of sales, we learned that success comes down to understanding how to balance the art of identifying and matching personas and the science of effectively structuring the organization for scale.
Understanding the art
Matching seller personas with complementary personalities on the buyer side is a crucial aspect of successful enterprise sales, and it's a matter of strategic importance for a CRO. In the realm of complex, high-stakes B2B transactions, building strong relationships is often as critical as the product or service itself.
The dynamics of enterprise deals involve multiple stakeholders, each with unique preferences, communication styles, and decision-making criteria. A well-matched seller persona with a personality that resonates with and complements those of key buyers and influencers within the enterprise can be the linchpin that secures a successful deal.
The consequences of a personality mismatch can be severe. Enterprises invest heavily in vendors they trust, and a negative interpersonal dynamic can erode trust and jeopardize the entire deal. Losing a large enterprise deal due to a misalignment in personalities can be a costly setback for any organization. Therefore, the CRO must master the art of putting the right people on the right account. Doing so involves not only understanding the technical aspects of the product but also recognizing the subtle nuances of human interaction. Per Gartner, sales leaders can increase their sellers’ odds of closing high-quality, low-regret deals by 157% simply by making their customers feel more confident.
By fostering connections beyond the transactional and aligning with the customer's values and culture, CROs can increase the likelihood of long-term success in enterprise sales, solidifying the company's reputation and revenue streams.
For guidance on how to get started, CROs and the leaders that report into them can begin by identifying four core personality types on their team before turning that lens onto the prospect’s leader buyers:
1. The Driver
Arguably the most prevalent sales persona, Drivers are results-driven and, as such, will want to control the sales process. That means they’re prone to challenge a speaker and skip casual conversations to hurry straight to the point.
As one CRO noted, sales organizations with large enterprise aspirations can fall into a trap by hiring too many of this type of seller. While Drivers can be great at closing smaller, more transactional deals, complex buying committees and guaranteed long sales cycles will require a seller with patience and the ability to listen actively to everyone in the buying committee.
2. The Analytical
Analytical buyers, true to their type, want to take their time to make a decision. They focus on weighing the pros and cons of a potential solution and will ask a lot of questions in the buying process. The best kind of sellers to interact with these buyers love digging into the details of the product or solution they’re selling and are just as curious as the buyers themselves.
The Analytical thrives on having facts and figures to help facilitate their decision-making. A Driver who fails to adequately listen or answer their questions (or an Expressive seller who relies on emotional engagement) could put a deal at risk from the get-go.
3. The Amiable
With its frequent rejection by buyers, the sales profession hasn’t always provided the optimal environment for Amiable seller types to thrive. With large enterprise sales, where buying committees are composed of all levels of potential decision makers, Amiables now have a better chance of success.
Where an Amiable buyer may seek feedback and approval from others in the buying committee to make a decision, Amiable sellers are able to fine-tune their pitches to understand better what the buyers want. Amiable buyers and sellers will need to be nudged into further action, however, as they’re prone to seek approval before acting independently.
4. The Expressive / Emotional
There’s no doubt that some of the most successful sellers are charismatic. When that charisma is natural and authentic, the seller can unify the entire buying committee into closing the deal. Since the heart of selling is relationship building, Expressive types, who are naturally team players, have no problem building the foundation of a strong partnership.
However, the results can be disappointing when an Expressive type focuses too much on talking and building relationships instead of strategically moving the deal forward. Expressive types can lack the discipline and execution rigor of their Driver counterparts because too much of their ability to get a deal done is based on intuition.
The Science
If the art of large enterprise sales is psychology, then the science is metrics and internal expectation setting. Organizations often make a critical mistake when hiring sales representatives for large enterprise deals by overly relying on personality profiles. While personality traits are undoubtedly important, merely "hiring on a profile" does not guarantee success in the complex world of enterprise sales.
Large enterprise sales require unique skills, including deep industry knowledge, solution expertise, and the ability to navigate intricate decision-making processes. CROs must look beyond surface-level personality traits and focus on a candidate's demonstrated ability to understand and address enterprise customers' specific needs and pain points. This means assessing their track record, problem-solving skills, and capacity to build and sustain relationships in a challenging environment.
Additionally, executive leadership often misjudges the length and complexity of large enterprise deal cycles. It's not uncommon for these deals to take significantly longer than smaller transactions due to the involvement of multiple stakeholders, meticulous procurement procedures, and rigorous due diligence. CROs must educate their leadership teams about the extended timelines typically associated with enterprise sales and set appropriate expectations. Rushing the process or expecting quick results can lead to premature judgments about a salesperson's performance, resulting in a loss of talent before they can demonstrate a return on investment. Patience is a virtue in enterprise sales, and CROs must advocate for it—never easy when a sizable target and a board meeting are looming.
A significant part of being a CRO is learning to get comfortable having uncomfortable conversations with internal stakeholders, including executive leadership. Leadership's involvement in the sales process can sometimes hinder progress, particularly when they overrule the CRO's recommendations about who should be part of deal negotiations. Deals have gone cold when leaders from different business groups disrupt the rapport established by the sales team with the buyer. For that reason, CROs must assertively communicate the importance of maintaining consistency and trust in these interactions.
They should also be prepared to have candid discussions with sellers who are not well-suited for particular accounts. It's essential to match the right personnel to the right opportunities and address any misalignments promptly to ensure the best chance of success in large enterprise sales.
There seem to be two schools of thought among the CRO community on the best way to handle these situations:
Some say that business is business, and moving a rep off of an account they’re not the best fit for is a given.
Others believe that shifting the rep into a different position on the account avoids potentially losing the rep altogether.
CROs can navigate these situations with a combination of expectation-setting with sellers from Day 1 and balancing decisions on how to navigate a potential sales captain change by evaluating a seller’s past performance and the immediate revenue needs of the business.
A Balancing Act
Transitioning into an enterprise sales motion can open a whole new world of revenue and investment for a company that does it right. As with any large shift in top-down strategy and operating rhythms, behavioral change, transparent expectation setting, and having the right people in the right place will be the difference between a successful scale and a painful lesson.
As we pointed out in a previous article, CROs must increasingly wear the hat of a Chief People Officer for their organizations. A big part of the job is getting to know the people who make or break the number and ensuring they’re in the role where they can best succeed.
What is the Numentum CRO Playbook?
A community-sourced guide that enables new and existing revenue professionals to quickly get up and going, optimize existing processes, and win in the Age of Buyer Experience. These aren’t theoretical insights: all information sourced herein has been provided by experienced Chief Revenue Officers from different industry verticals and company maturity stages.
See something you’d like to comment on or contribute to? We’d love to hear from you. Shoot us an email at info[at]numentum.com with the subject line CRO Playbook. You can also contact us here.
