B2B SaaS – The Unique Mentality of Top Enterprise Sales Pros

June 21, 2022

To understand what it takes to achieve exceptional performance in enterprise sales, as opposed to mid-market or SMB sales, I recently interviewed a dozen experts whom I regard as my informal “brains trust” on this topic.

This group included three former CEOs; several former major-account execs at global players such as IBM, Cisco, and SAP; a former global sales MD on IBM’s executive leadership team, three B2B SaaS sales leaders, and a headhunter who specializes in hiring sales reps, sales managers, and CROs.

Just to set the context, I asked each person to summarize what they perceived to have changed in the SaaS era with respect to the dynamics between vendors and enterprise customers.

What’s Changed vs What’s Remained the Same

To acknowledge what’s changed since SaaS began to replace the perpetual license business model, suffice to say that, yes, certain aspects of customer buying behavior have indeed changed - such as, for example, prospects getting further along in their consideration and evaluation due to the much greater availability of information online these days. From the vendor’s perspective, the customer engagement process has been de- and re-constructed to reflect a more explicit commitment to customer success and to accommodate more extensive automation of distinct demand creation and demand fulfillment tasks, in support of marketing, sales and customer success teams.

That said, it is my belief that a lot has remained constant, particularly in terms of what it takes for vendors to successfully engage with large customer organizations, whether corporate or state-owned. For example, there are still (at least) half-a-dozen stakeholders in different parts of each organization to deal with, buying decisions are still beset by complex political, financial, and technical considerations, and helping customers to achieve mission-critical business outcomes is still a relatively rare skill, and vitally important to building successful vendor-customer relationships at this level.

Most large national and multi-national organizations still prefer to deal with vendors who take the time to understand their requirements and are willing to field a team of sales, solution architect, PS, and customer success staff to ensure that their implementations run smoothly and that users adopt the technology productively.

The Unique Mentality of Top Performers

With this in mind, I was particularly keen to pin down the elusive, sometimes unorthodox traits of high-performing enterprise salespeople and account managers that escape popular characterizations of this branch of the sales craft.

Often, these individuals have followed an "atypical" path into sales, via product management, systems engineering, development, sometimes even as customers or as executives in a different, non-tech industry. This role is a critical catalyst in any tech company that deals with large enterprise or government organizations, but it is quite tricky to recruit for. My interviews were invaluable in helping me to identify seven traits that make up the mentality of many if not most top-class performers. My hope is that one benefit of this research might be to make it easier for organizations to identify the right candidates to attract.

Here are the main elements we identified:

  1. They tend to be unconventional thinkers, contrarians even. Curiosity is one of their trademarks. They want to understand the Why before worrying about the How. And they have no qualms about testing a prospective customer with penetrating questions, to find out what makes them tick, what critical problems they are trying to solve that they may not yet be giving voice to. In contrast with those who’ve grown up thinking that you always have to say “Yes” to every customer request, they realize that “No”, framed in an appropriately courteous but firm manner, can be one of the most powerful words in Sales.

  2. They aren’t necessarily extrovert, or great talkers, in fact they can be quite unassuming – besides asking good questions, they listen carefully to the answers, and then ask a deeper question to “peel the layers of the onion” to get at the essence of what their prospect needs to accomplish. They also resist the urge to spout speeds and feeds, or leap into presentation or demo mode, knowing that this can quickly turn into one of those show-and-tell sessions where the prospect’s eyes quickly glaze over, and they end up none the wiser regarding the latter’s real motivations to buy.

  3. They think like entrepreneurs who are running their own business – they see their territory or list of named accounts as their target market, to be cultivated with due care rather as crops on a farm that need to be planted, watered, and eventually harvested, all in good time. And they are not fazed by the need to operate in a situation of considerable ambiguity, just as most entrepreneurs frequently need to do.

  4. They see themselves as “resource allocators” – they realize that the resources they represent – products, services, domain expertise, partner relationships – are precious and therefore they prefer only to deploy them when they find the right fit, rather than splashing them too willingly, as less accomplished salespeople are wont to do. This single factor has been cited in prior research into customer buying criteria as a prominent reason to choose a specific vendor over their competitors - i.e., the command that the sales rep demonstrated over their company's resources, to deploy them at the appropriate time - not before, not after, nor in an indiscriminate manner.

  5. They don’t believe in taking the first, easiest deal that presents itself – they are patient about building a thorough case for action and don’t move into “closing” mode until they are convinced about how they will be able to produce the biggest impact for their customer. They are entirely comfortable with the decision to turn the wrong deal down.

  6. They realize that a poor fit will result in bad outcomes down the line – if a customer makes a purchase that they live to regret, they know that the whole experience will come back to haunt them, so out of a sense of self-preservation as well as “relationship preservation” they do everything possible to avoid falling in this trap. They are also comfortable in admitting up-front to limitations in their company's products and/or services.

  7. Above all, per the Sun Tzu quote above, they consistently outthink (outwit) and even outwork their competitors – they think continuously and deeply about what’s really at stake for their prospect, how best to help them solve their mission-critical problems, who their real competitors are – including the daunting “do nothing” option for customers – and how to differentiate their offering in each specific customer context.

Thus, although these top performers may not see themselves as hard workers per se, they expend great amounts of mental and psychic energy thinking about the political dynamics in their customer’s organization: who is the real decision-maker, what kind of veto power different executives and managers have, who or what is their actual competition (so often, the status quo is a stiffer opponent that any competing vendor), how severe is the business problem being discussed and what is the unacceptable consequence to the customer’s business of not acting, why now is the time when the customer must act, and so on.

If by now you’re thinking that some of the characteristics I’ve described above are not literally unique to this sales role, you’re probably right. But I’ll wager that one or other of the attributes mentioned here weren’t on your list at all!

Many of these top-class exponents/performers later become senior executives or CEOs – or they choose to remain in their account executive roles because of the considerable satisfaction that they derive from what some of them see as their professional calling.

Philosophically, these individuals tend to be optimistic in outlook, though not prone to getting carried away with enthusiasm. They do everything possible to optimize the environment around them – indeed, they prefer to work smart rather than work hard, and they make it their business to figure out who they can consider to be on their virtual as well as core team, and how to leverage these precious resources (including when to deploy their execs to good effect). And they take risks, but calculated ones – so they manage risk with a focus on gaining a suitable reward from doing so for both their customer and their company.

Enterprise Sales - Essential Skills According to One Sales Leader

Now for some of the essential skills that a sales leader should expect from their enterprise sales AEs. For this I’m borrowing from Paul Limbrey, a senior sales leader at Google. Limbrey was formerly a highly successful major-account executive at Cisco and then SAP, and for the past several years has been managing director of global ad agencies and partners at Google. In contrast with most other sections of the company which target their hundreds of millions of individual users, this group operates as a bona-fide enterprise sales operation.

Limbrey shared with me the five qualities that he refers to as his “Five P’s”. He teaches these skills to his sales teams who deal with managers and executives in global ad agencies such as WPP, Publicis, and Omnicom.

Paul Limbrey’s “Five P’s”

  • Provocative – In order to get the right dialog going with a prospective customer, the AE needs to have formulated a point of view of the end-customer’s predicament – and how to address it - that is sufficiently well thought-out and provocative to get the attention of a busy executive.

  • Persuasive – The AE needs to be persuasive enough to convince the customer that it is worth acting, rather than deferring a decision to an undetermined future time (the lack of a perceived case to act Now is one of the most common reasons for opportunities to slip or become no-decisions).

  • Political – AEs must be politically savvy enough to figure out who in the target organization needs to be included in the process, who the key decision-maker is (as distinct from the various gatekeepers and veto holders), and how to gain access to them.

  • Prescriptive – When they do manage to get in front of their target customers, they should already have a step-by-step prescription in mind regarding how the business problem can be solved, and why their company is uniquely equipped to help them.

  • Proactive – Finally, they need to be a persistent, creative thinker, ready to make things happen rather than merely hope that the right things will happen.

Every sales leader most likely has their favorite magic list, but this one seems to me to be as good as any, and better than most.


More general qualities to look for in exceptional performers include resourcefulness, ability to develop a following among their customers, and a natural propensity to become trusted advisors because of their ability to wear well over time with their customers and prospects.

My belief is that the more companies appreciate the combination of unconventional mindset factors and strong “Five P’s” skills required in high-performing enterprise sales professionals, the more successful will be their recruiting efforts for this somewhat rarefied role.

Afternote: My thanks are due to the following people who were generous enough to brief me on their thoughts about this important role: Ken Bado, Todd Clyde, Pete Daffern, Piers Fox, Steve Glass, Richard Goat, John Hamm, Paul Limbrey, Marty McMahon, Peter Vanderfluit, Randy Walker, Paul Young.