Sales Transformation Through Insight-led Selling

The Challenge

Just as gravity pulls objects down to earth, market forces draw companies toward a state of “competitive parity” in which customers can choose from among several similar vendors for similar products. This parity is aggravated by the ability of customers to use easily accessible information to dictate what they want, thus putting vendors further on the defensive. The result is lower growth and lower prices, and increased pressure on sales leaders.

To differentiate themselves from competitors, leaders often focus on a stronger product/service portfolio and broader solution focus. While a broader set of offerings and a solution-selling approach is beneficial, it also tends to introduce more complexity than customers can handle. As a result, management strives to adopt a “trusted advisor” approach where the sales rep’s role shifts toward helping customers sort through complexity and achieve desired outcomes.

This is a worthy and yet difficult form of sales transformation. First, it requires a higher-value dialog with senior buyers – a dialog that Sales earns by sharing valuable “insights.” Second, while “insight-led” selling can lead to sustained share and margin gains, it can also be costly and disruptive when done poorly.

The Solution

We believe the ability of the sales force to generate and communicate meaningful insights has become one of today’s key sales leadership competencies. Insights may address the customer’s industry, business model, productivity, competitors, or future. They must be valuable to customers and somehow link to your company offerings. This sales motion, which we are calling insight-led selling, can change your positioning with the customer from a vendor pushing product to a partner that adds value. Without it, the sales force remains trapped in the shrinking “features/benefits” loop.

Based on hundreds of consulting projects with Global 2000 companies, The Alexander Group has identified two key challenges leaders must address to effectively conduct insight-led selling:

  1. Developing a sustained flow of insights
  2. Maximizing the impact of insights in the sales process

This article is focused on the first challenge. To begin we must consider the various resources or “players” involved in an insight-led selling motion.

The Players

A sustainable Insight development process is a collaboration challenge across several roles and functions, including:

  1. Sales Reps
  2. Marketing Analytics Group
  3. Sales Training Group
  4. Data-Mining Team
  5. Vertical Marketing Experts
  6. Sales Specialists/Overlays
  7. Sales Strategy/Planning Team
  8. First Line Manager Coaching (OJT)

Moreover, it requires coordinated Insight-sourcing across the following processes:

  1. The Sales Process: A systematic process is required to harvest insights from sales reps and equip other reps. Being at the heart of the sales dialog, reps are a key source of customer insights and feedback. However, rep insights tend to be improvisational, anecdotal, highly personalized, and customer-specific. And when a rep has a great insight, it’s typically not shared due to internal competition. Furthermore, once insights are harvested, reps tend to aim too low in the customer organization (where they are comfortable), thus wasting insights on non-decision makers.
  2. Marketing Analytics: Marketing Analytics is an increasingly common sub-group in the marketing organization tasked with conducting research on customer needs. However, because the focus of this group is often on Product Development, Pricing, or ranking vendors (on price, service or product), they don’t typically identify breakthrough sales insights, let alone package them up for sales reps as part of a guided selling process (i.e., sales playbooks).
  3. Sales Training: Training leaders typically see the need for insights to optimize sales effectiveness, but lack the resources and expertise to develop them. Indeed, with increasing pressure for a clear training ROI, they are acutely aware of the danger of “spinning,” “advantaging,” or “challenging” customers without the compelling insights to back it up, i.e., argumentative reps don’t close.
  4. Customer Data Mining: Vendors increasingly have data on how customers use their products, often coming from their customer service team or cloud applications. However, sales insights only emerge if someone with a strategic perspective systematically reviews the data to identify common challenges, usage gaps and best practices. Looking beyond traditional sales optimization ideas, this process needs to find breakthrough insights to capture the attention of senior buyers.
  5. Account Planning: An effective account planning process forces reps to analyze customers more deeply, often yielding valuable insights to be systematically extracted and shared. However, the real insight payoff comes from joint-planning with customers, particularly when senior buyers participate. But here again, the challenge is systematically extracting these insights from reps throughout the sales force.
  6. Win/Loss Analysis: Win/loss analysis is a major source of great insights (albeit some insights gained here are already being used by competitors) and should be a standard practice. The challenge is sorting through the different perspectives (including buyers if possible), to identify real strategic insights and not settling for operational buying criteria such as price, product or company platitudes.
  7. Vertical Marketing: Large marketing groups may have several experts focused on developing collateral to help reps sell to specific industries. These often contain leveragable insights for sales, but typically at a generic industry-wide level.  Too often these experts are also product-focused and out of touch with sales realities.
  8. Value Realization: This is an increasingly common function, designed to ensure customers get full value from their purchase so products don’t become “shelfware” and get displaced. This role should be an excellent source of insights as it combines elements of on-going impact analysis, training, evangelical selling, account management and best practice dissemination.


Overall, the best practice companies that we consult with have assigned ongoing accountability for insight development to groups that act like cross-functional “gardeners,”  systematically nurturing the insight sources, pruning back the operational perspective to find breakthrough insights, and helping new insights bud from old ones. These groups also work hard to systematize the process for harvesting and disseminating insights to the sales force. They also manage them on an ongoing basis, calibrating them by seeing them in action, and refining them over time.

So far, these types of effective “Insight Gardener” groups most often sit in Marketing, but typically also have some regular participants from Sales and Product groups as well. More important than where they report is that they have a strong leadership charter, highly-capable personnel who understand Sales, and sufficient capacity to stay focused on generating new and fresh insights. This is not a part-time job! Indeed, the best practice companies we have seen manage insight development as a continually running business process, with inputs, processing steps, quality control, outputs, and constant readjustment based on user feedback.

We hope you have enjoyed this brief overview of the operational elements needed to drive Insight-Led Selling on an ongoing basis.

For more information on this topic, please visit the Alexander Group.

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