Sales Excellence | Approaching Sales As A Quantifiable Skillset For Assessment

At many organizations the definition of a top performer in a sales team can be somewhat ambiguous. While sales performance tends to be measurable in terms of closed deals and revenue contribution, there are other meaningful measures that lead to sales excellence. This post aims to demystify how we think about sales performance, and ultimately excellence on the sales team at Ashby.

First off, it’s helpful to think of sales performance as a two-layer system. Layer one is foundational and consists of raw attributes and characteristics that most great salespeople possess. These attributes tend to be innate or habits learned early in one’s life and career. In this foundational layer, you could score highly in any of the criteria even if you haven’t done sales. Conversely, since these tend to be personality traits and values, they tend to be a bit more static in nature, and so primarily need to be assessed during the hiring process. That said, it is up to the individual how quickly and how meaningfully they might improve their foundational abilities to improve as a seller.

Layer two of the system is built upon that foundation and consists of the functional skills and abilities that great sellers have developed over time. In this functional layer, skills are honed over many years, and the best sellers pursue continuous improvement decades into their sales career. In this layer, it’s extremely uncommon that someone would be great at any, never mind all, of the key functional areas of sales without both the practice of experience and a growth mindset.

Layer 1: Foundation

Theme 1: Diligence (Work Ethic, Grit, Persistence)

Sales is a numbers game. You can literally out-work other sellers to produce greater results. If you’re smart and lazy, don’t go into sales! There are other professions much better suited to that profile.

Diligence means continuously prospecting when you’ve got a good pipeline. It means thoughtfully drafting and sending same-day follow-up emails after doing six demos in one day. It means proofreading an important email one more time before clicking send.

Unfortunately, there is no substitute for the consistency of doing high quality work in sales. Quite often a grinder is the most consistent top performer, outperforming an intellectual.

Theme 2: Intelligence (Curiosity, Learning, Adaptability)

Great salespeople are smart and insatiably curious. They love learning new things and embrace the unknown. After all, you have to love learning about companies and their problems and creatively positioning your solution to meet their specific needs. Excellence in this area means expressing genuine interest in new topic areas and new initiatives. It also means that you’re a self-starter that will actively seek out the information you require rather than wait for it to be perfectly served up to you. A great rep frequently develops new domain expertise and uses that to build credibility with their buyers.

Selling is a dynamic process; as we learn more, we must be willing to try new things. Markets also shift and we must adjust with the market. Great salespeople are highly adaptable. They enjoy refining and adjusting their approach to maximize their impact.

Because the great salesperson is intelligent, they learn new material quickly, and consistently pick up on new details and nuance from customer conversations. They also prioritize revenue-generating activities by identifying which accounts and activities are high-yield, and focus on those.

Theme 3: Communication (Listening, Clarity, Energy)

A core competency of every great seller is that they are exceptional in their communication skills. They are incredibly precise with their words and can distill a complex idea down to its essence to convey rich meaning in a few words. The ability to bring clarity to a conversation helps create understanding and alignment.

Great sellers are equally strong at asking questions and listening. They ask questions like a surgeon uses a scalpel—adeptly. Listening is a strength of sellers because they’re genuinely curious about what the other person’s perspective is, and they understand that by listening they can learn, and use that information later. The best sellers are often more excellent listeners than skilled speakers. Buyers tend to highly rate sales conversations in which they spoke much more than the salesperson. In my experience this is most often achieved by salespeople who are precise and effective communicators.

Theme 4: Empathy (Understanding, Tailoring, Solution-seeking)

Perhaps adjacent to curiosity is empathy. Empathy is the capacity to understand what another person is experiencing from their frame of reference. It’s the capacity to place oneself in another's position. Exceptional sales people aim to understand the nuances of their customer’s context because, by gathering a full understanding, they can better craft or position their solution for that specific customer.

An excellent sales rep can uncover the relevant facts and tailor their solution to address the buyer’s most pressing priorities. To do this, they are skilled at working in teams, especially with internal stakeholders to seek out or create new solutions for the customer if the organization can provide it. They can navigate complex situations to identify mutually agreeable options.

Layer 2: Functional

I’ve broken down this second layer into two component areas:

1. Territory Development
2. Deal Management

These two areas within the functional layer form the basis of what all great salespeople consistently do well: finding and closing deals.

Top salespeople take all of their fundamental attributes and values and develop those over time into the following functional skills:

2A: Territory Development

Pillar 1: Territory Planning

All great reps create a plan of attack for their territory. This is true whether they own five Fortune 100 accounts and need to whitespace the myriad product offerings and services those accounts own or whether they have a geographic territory that has over 10,000 companies in it. All great reps take the time to analyze and prioritize their territory.

The territory planning process typically takes place infrequently (usually annually) and involves analyzing all available data to:

1. Rank and prioritize accounts
2. Identify specific plays or “bets” to place early
3. Create a coverage model and action plan for remainder

A rep without a plan, or a rep not following their territory plan, will chase shiny new leads rather than focusing on the accounts with the highest potential and propensity. Reps who build and follow a territory plan outperform because their conviction and focus drive results where the scale of those results can be meaningful.

Pillar 2: Pipeline Generation Activities

With a plan in place, top reps start putting the wheels in motion quickly and do so consistently. They only focus on what they can control—the inputs—and trust that the results will come.

Great reps are innately persistent in their pursuit of pipeline. They combine their acumen, creativity and diligence to create new campaigns and approaches and then adapt and iterate based on changing market conditions.

Top reps strike a balance between highly personalized outreach to their top accounts and tailored but programmatic outreach to Tier 2 or 3 accounts. If partnered with an Associate or BDR, a top AE will create clarity for ownership and activity accountability.

An excellent salesperson enjoys the hunt and loves nothing more than creating new deals to fill the top of the funnel. The reps that overachieve goals most consistently are always the ones who are great at filling the top of the funnel and don’t primarily rely on other sources of leads such as inbound and partners.

2B: Deal Management

Pillar 3: Discovery

Top reps show up to every call with an informed perspective on their solution and the account. They don’t use discovery as a substitute for preparation—a cardinal sales sin. Instead, excellent salespeople will often present or discuss a bit of their perspective on the market first, to rapidly build credibility. Then, with the implicit permission earned, they’ll ask a handful of questions with surgical precision.

Many sales reps ask lots of questions because they've been taught that more discovery = better. That's wrong. You want to get as much useful information in as few questions as possible. Instead, as the deal progresses, ask more questions based on the context of the current discussion. Discovery is not a first call, but rather a theme carried on throughout the entire deal.

Top reps also understand that an effective sales motion is about a consistently mutual exchange of information (and power) and they use questions as a tool to reframe the evaluation, or to engage additional stakeholders. (“What reports are most important to your VP of Engineering or CTO?”)

Excellent sales people also use discovery to qualify out an opportunity. Because they’re ruthless with their allocation of time, they don’t want to work on a deal that will ultimately waste it. If a deal is not viable for any number of reasons, they’ll quickly point the buyer in the direction of a different company. That said, if a little bit of creativity could help them design a unique solution, they’ll vet that out first!

Pillar 4: Stakeholder Engagement

The rigor of account planning and stakeholder mapping will vary between a salesperson covering Startups and a one covering Fortune 500 accounts, but some amount of account-level planning & research are always required to be well prepared and identify all of the stakeholders. Great reps can quickly gather all of the right information from both public and internal data sources to create a complete view of an account and its stakeholders.

Top reps also consistently re-assess the full set of stakeholders, both influencers and decision makers in their accounts and use the account mapping exercise to create a plan for peer-level engagement. They understand that sales in a team sport and they lead an internal team including senior management as part of their sales campaign to minimize risk for the buying committee.

Pillar 5: Solution Presentation

Top reps have a voracious appetite for knowledge about their solution, and their buyer’s challenges that drive them towards it. When it comes time to present their solution, the rep can clearly articulate the situation their customers most often find themselves in and logically explain the reasons buyers specifically chose their solution. They’re also quick to point out why you might choose a competing solution if necessary.

A strong rep consistently takes the time to learn about the competition so as to be highly knowledgeable and not at all dismissive of the technology landscape. By being intimately versed in competitive knowledge, the best reps can have a constructive conversation with buyers about differences, and what downstream impacts those might have on a workflow.

Excellent reps will consistently tie the features and capabilities they present to the ways in which users create new value for their business. Great reps do this without overusing the word “value,” which is wildly overused in sales conversations.

Pillar 6: Project Management

There’s no shortage of research on the increasing size of buying committees. Bigger buying committees makes the task of reaching a consensus decision ever harder for the buyer, never mind the seller. Top sales reps are exceptional project managers. They present a compelling series of steps for the evaluation of their solution and can clearly articulate the need for the right set of stakeholders at each step of the process.

For deals of any materiality strong sales people will continuously share and update the project plan so that no surprises show up at the end and derail the timeline or add unnecessary risk (InfoSec reviewed this, right?)

In the largest deals, the top rep acts as the main coordinator of resources and activities taking place on both sides of the table. They shepherd the process forward and address risks and issues throughout. They see around corners and proactively prevent issues from happening before they arise.

Pillar 7: Negotiation

Top sellers understand that negotiation doesn’t just take place at the end of an opportunity, once your solution has been selected, but that the entire cycle is an extended negotiation. They’ve refined their ability over the years to negotiate the process of the evaluation such that they tilt it in their favor. They’re very comfortable navigating creative quid pro quo exchanges. (“I’d be happy to fill in your security questionnaire if we can set up our CEO with your VP of People for 20 minutes next week.”)

When it comes to commercial conversations, top reps draw on their desire to create a win-win solution for both parties. They are confident that they’ve established substantial and quantifiable value during the presentation process, so they have a solid platform to stand on.

Excellent sales people seek to understand the specific desires (ie “reduce OpEx this year”), and not just the generalities (ie “lower price”) when negotiating. And they never, ever, negotiate against themselves. (“Here’s a discount you didn’t ask for.”)

While negotiations can sometimes get contentious with each party trying to act in their own best interests, top reps consistently exercise empathy and intellect to seek out mutually beneficial scenarios. They also acknowledge that sales is a team sport, and will negotiate to loop in leadership on both sides to expedite the process as needed.

Sales Excellence

Being excellent at sales is a combination of foundational characteristics and attributes as well as the execution of complex functional competencies learned over hundreds of sales cycles. We use this framework here at Ashby to discuss both performance and career development.

This model provides a rubric by which salespeople can aim to objectively assess the skills that ultimately lead to their performance. I highly recommend doing a self assessment.