Sales Enablement

How AI Can Help Sales Teams Craft More Personalized Pitches



Progressive sales leaders have used AI and machine learning to increase the efficiency of their organizations. Revenue operations and enablement teams have fine-tuned advanced models built for the structured data housed in tools like CRM systems. Many vendors have offered powerful ways to identify patterns and suggest new sales methods, improvements in forecasts, or even modifications to sales incentives.

But recent innovations in generative AI hold the promise to deliver value directly to the seller by transforming a key part of their job that most get wrong: breaking through the noise and engaging customers in relevant ways.

A recent survey found that only 13% of buyers agreed with the statement: “The seller’s message is addressing a relevant challenge my organization is facing.” The same survey showed that only 25% of buyers agreed with the statement: “The seller understands my role within my organization.”

It’s clear that too many salespeople undermine their own effectiveness by not demonstrating an understanding of their buyer’s role, business, and market.  Not only does the evidence suggest buyers are turned off by irrelevant engagement attempts — studies estimate the response rates to this type of outreach to be no higher than 1% — but, even if a seller is able to earn time with a customer, sales approaches that lack relevance and resonance imperil chances of a close.  Sales leaders we have spoken to recently report conversion rates that stubbornly hover between 20% and 25% despite years of investment in training, messaging, and other forms of sales enablement.

A Revealing Truth

To better understand how sellers can boost the relevance and resonance of their sales engagement efforts, our team tested different engagement approaches with a panel of several hundred C-level executives.

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When sellers demonstrate a lack of understanding of the client’s business, it’s nearly impossible to compel action with buyers. In our study, buyers were quick to critique email communications that felt impersonal or half-hearted, such as this example sent from an average-performing sales rep:

Subject: Boost Catalonia’s win rates by 12.5%


Is your team struggling with low customer engagement rates due to the inability to deliver highly personalized experiences? Would you be interested in learning how organizations like ServiceNow, Salesforce and Intel are increasing win rates by 12.5% by delivering highly personalized customer experiences?

Leveraging our AI-powered solutions we’re able to help your team deliver highly personalized customer experiences across all channels, leading to an increase of 2.6x in pipeline and 12.5% higher win rates.

Worth exploring how we can deliver these outcomes for your team?

Best regards,
Ray Clark
TechSync Solutions

More than two-thirds of the buyers in our study found communications like this to feel robotic and impersonal. In this example, the seller does not demonstrate any knowledge of this prospect’s situation or role. Nor does the message convey any relevant detail on exactly how their solution delivers on the outcome or how it might differ from other providers.

One executive we interviewed admonished sellers to “Be sure to know something about the business you are selling to. Do your homework and don’t make it look like I’m the 15th call you’ve made with the same 15 words to try to get a demo with me that will only take 15 minutes of my time.” Another lamented “Personalization is not about mentioning my alma mater or rehashing something I posted.”

We also tested the impact of highly tailored and contextualized outreach on buyer engagement.  When sellers can convey a deep understanding of the buyer’s business, their efforts are far more likely to break through and generate interest from a customer. For example, when presented with various outreach examples, the panel of buyers in our study — across all c-suite functions — reported a strong preference for emails like this one:

Subject: Boost Catalonia’s revenue growth


On your Q1 earnings call, Kelly Smith highlighted the importance of extreme focus on net new customer acquisitions and how that will help achieve your 19% revenue growth goals in the next fiscal year.

However, over the last 12 months your revenue growth rate was only 7% and the second lowest in your peer group. A recent Forrester Research report indicated many enterprises struggle to deliver personalized experiences across multiple touchpoints, hurting pipeline creation and weakening Net Promoter Scores. Leveraging AI powered engagement modules, TechSync Solutions empowers ServiceNow, IBM, and Salesforce to provide personalized experiences and seamlessly engage customers across various channels, leading to 3.2x bigger pipeline creation and 21% more revenue growth.

We identified an opportunity to drive $34M incremental revenue, helping you reach your growth goal. When is a good time to discuss this?

Best regards,
Ray Clark
TechSync Solutions

This seller has clearly done their homework on key buying committee members. The email references goals that are specific to this company. The message includes context around how they compare to other peer companies and how their solution addresses the customer’s multi-channel needs. As one buyer reacted, “I liked that they are tying impact to financial performance and my company’s KPIs while addressing my priorities. I am usually skeptical of generic promises to increase ROI but here they added social proof and use cases to reinforce their case with data.”

This isn’t just about cold outreach, of course, or writing better emails. It’s about doing better across the entire sales cycle with great meetings all along the way. But ineffective outreach often leads to a vicious cycle for average performers. Most sales organizations already have too few reps achieving annual sales quotas. As sellers fail to resonate with buyers across the journey, they fall even further behind goal and resort to more “spray-and-pray” tactics in hopes of hitting their number.

A Different Approach

Most sellers understand that a tailored and personalized message is better than an impersonal and irrelevant one. But, historically, hitting a high-quality bar in all forms of communication requires two things for a seller: a lot of time to do research and an awareness of what to look for. High performers succeed by overweighting time and attention to homework early in the sales cycle, finding different types of information, and then deploying that knowledge to convey a rich understanding of the buyer’s business.

As part of our study, we interviewed high and average performing salespeople about their data consumption habits and, when combined with buyer observations about information they value, found the best sellers focus on three types of data in their customer engagement efforts:

Mutual Fit

This is primarily about proving a true match between the buyer’s business and the seller’s solution. Here, the rep seeks out verified and verifiable information — ideally, where possible, using the buyer’s own data — to qualify opportunities and prove that there is a fit. The seller uses that data to show that their solution is particularly well-suited to help companies like the buyer’s.

Data that reveals the customer’s strategic priorities can help reps assess areas of alignment. Information pulled from financial reports or recent news items can indicate senior leadership intent — where they are going, and for what reasons — and can be a powerful way to map near and medium-term partnership goals.

Public companies frequently communicate in formal settings at investor conferences or in quarterly shareholder calls. Today’s generative AI-powered software provides cogent summaries that help salespeople connect the dots to potential opportunities. As one high-performing seller put it, “I love using verbatims from recent shareholder calls as a way to show I have my finger on the pulse of their leadership priorities.”

Personal Value

This is primarily about personalizing the motive. Here, the rep is seeking a full and complete picture of the organization and the individuals involved to tie their solution to the individual priorities of their buyers. Doing this requires the seller to understand how key stakeholders would view success and failure, on both a personal and professional level.

AI-enabled platforms like LinkedIn’s Sales Navigator combine first-party data and firmographic insights to provide organizational views, including how buying committees are connected. The user-generated profiles, for example, assist in keeping data accurate and allow for timely, account-level insights such as key stakeholder role changes.  Business case builders that filter all the way up to boardrooms or reflect investor sentiment can help communicate messages that resonate with C-level executives. Other AI-powered tools like Databook serve up recommendations to consider other potential stakeholders and allow for viewing stakeholder priorities side-by-side for easy comparison.

Time-Spend Justification

This data is primarily about substantiating timeframes. Here, the rep seeks information that validates the “why now” reason for change.

The burden of proof is higher here for two reasons. First, buyers are aware most salespeople are incentivized to shorten decision-making timeframes. Second, decades of psychological studies show people are wired to choose the “do nothing path” more often than not.

Seller time here is best spent finding corroboration that timing is of the essence and purchase exploration is a warranted, good use of the executive’s own time. The most obvious place to start involves third-party analysts who may detail potential investments worth considering. Some teams use insights around end-of-year fiscal planning to make financial cases for change that highlight time-sensitive assumptions or contingencies.

Top performers also recognize that timing is a moving target that can shift as new priorities come to light. One rep shared with us that they pay close attention to when management signals a change in course, particularly in situations where it’s clear the change came as a result of keeping pace with their competitors. These signals might be sent in investor calls, CEO interviews, or public presentations given by senior leaders.

Software platforms can ease the process of tracking such wide-ranging information on an ongoing basis. Databook, for example, allows users to monitor peer benchmarks on “move-the-needle” business metrics. Large gaps relative to the benchmark can indicate the timing is ripe, as might new entrants into the peer set due to market innovations or product releases.

AI-Powered Homework

The evidence clearly indicates top sellers engage in frequent and different prep-related activities. In the past, hours of leg work and research were required to create relevant and resonant sales interactions. With seller time at a premium, this sort of intensive prep work typically falls by the wayside for average sellers. But advances in AI are fast removing the excuse that this type of prep is too time-consuming. Modern sales platforms have the potential to help the average seller get to expert-level preparedness, in a fraction of the time, increasing their relevance and credibility with buyers.

In fact, the best tools are already doing much of the right homework behind the scenes on behalf of the seller. This example, delivered in a messaging app, demonstrates the power of an AI engine capable of making proactive suggestions for well-timed outreach:

On the September 6 Q2 Earnings Call, Jane Smith (CEO) emphasized the importance of their initiatives to scale with efficiency in their go-to-market capabilities. This is an opportunity to demonstrate how Acme Company can help drive scale and efficiencies within go-to-market teams by increasing the number and quality of C-suite conversations.

Send this outreach to the below key stakeholders within the sales buying group to align Acme Company as a tool that can help the company execute on its strategic priorities.

Oscar Meyer, SVP Enterprise Sales
Michelle Scott, VP Strategic Accounts
Jason Lee, RVP Sales Northeast

This automated prompt provides a tailored background relevant to this specific company. Sellers can easily modify the scripted outreach to reflect their own voice. And the specified audience removes the guesswork as to where this will resonate.

High performers also know quality prep is not a one-time per-deal activity completed early in a cycle and then put aside until later. Relevant data is dynamic, not static, and changes as new information comes to light. The tight fit and match that was proven early might start to come apart as the decision progresses. And timeframes can change quickly, requiring that sellers stay abreast of changes in the customer’s organization and in their market.

Improving the effectiveness of sales team communications also does more than increase win rates. After all, communicating in relevant ways helps build buyer  relationships that begin on solid ground pay dividends over time. They help avoid post-deal dysfunction. They avoid customers recanting their decisions, invoking cancellation clauses, or asking to be let out of their agreements. Therefore, focusing on AI-powered prep-related activities should be high on the radar for sales leaders seeking to build long-term, meaningful customer relationships that grow and strengthen over time.


This article was written by Harvard Business Review and originally published here.



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