Chapter 2

Four challenges preventing enterprises from closing more deals

Legacy enterprises benefit from having an established name in the marketplace. But disruptors have the benefit of starting from scratch with their sales organization and sales technology stack. But enterprises don’t have to settle for inefficient processes or technology hampered by legacy systems if they can just improve in four key areas.


Sales has a transparency problem

Until we understand how salespeople work, we can’t give them the tools they really need.

Organizations are investing in technologies to foster collaboration and ensure everyone has the information and tools needed to succeed, no matter where they work.

But, while most teams—accounting, marketing, HR—operate with a certain level of autonomy, there is still a high level of visibility and accountability around how they spend their time. In contrast, every member of the sales team works differently. They have their own preferences for communicating, a schedule for talking with customers versus doing “paperwork,” and a unique perspective on using technology in the sales process. That’s why it’s important for sales tools to fit a salesperson’s needs and not the other way around. If sales won’t use the expensive, customized CRM system, then it’s more of a liability than a benefit.

Getting the technology stack right starts with an understanding of what sales needs and wants.

small figures on colorful blocks

That’s why it’s important for sales tools to fit a salesperson’s needs and not the other way around.

If sales won’t use the expensive, customized CRM system, then it’s more of a liability than a benefit. Getting the technology stack right starts with an understanding of what sales needs and wants.


Poorly designed tools frustrate salespeople and hamper adoption.

When sales tools are inconsistently designed, or poorly integrated with other systems, adoption plummets. The result: incomplete pipeline data that impacts every part of the business.

Before you can know where you’re going, you have to know where you are. To make more meaningful, strategic business decisions now and in the future, sales leadership needs access to real-time, quality data about sales opportunities. With accurate and up-to-date information on current, potential, and even missed opportunities, and an understanding of how and where salespeople spend their time, leadership can quickly identify what’s working and what’s not.

Properly implemented sales technologies share three main commonalities in successful organizations. They are:

  • Designed for the end-user with a consistent user experience (UX).
  • Fully integrated with each other and with the entire marketing stack.
  • Consistently adopted across the organization.

Without these three things, leaders will make decisions on everything from strategic direction to daily workflow processes based on incomplete or inaccurately represented data.

Of the three “must-haves” mentioned here, adoption is the most critical. Even poorly implemented sales tools can yield helpful information if the data collection is done consistently. A Forrester report on salesperson-centric software found that industry leaders judge whether or not to invest in sales tools by analyzing adoption rates of the tool at companies similar to their own.1 

When the tools sales uses are designed with their habits, preferences, and needs in mind, adoption will naturally follow.


Each of these customers is not like the rest.

When sales doesn’t understand the customers’ needs or where the customer is in the buying cycle, every call is a cold call. 

Almost without exception, business environments today are full of legacy vendors and disruptive startups alike, all after the same budgets from the same contacts within companies. To a buyer, vendor websites and vendor marketing materials can all look very similar. So, it’s in the details of the sales process where deals are made or lost.

For conversations with prospects, sales teams need to know more than just contact information and at which tradeshow the prospect stopped by the booth. They need to know what the prospect’s existing tech stack looks like, what kinds of problems they’re encountering, and even what content on your website they’ve already viewed. 

When working with existing customers, where the probability of selling new products and services is as much as 50% greater than selling to new customers, there’s no substitute for timely and relevant data. What does their tech stack look like? What products and services are they using now and what additional products have you already discussed with them? What’s their budget cycle, and when do they normally make buying decisions? All of this is critical information to have on hand when a buyer is ready to open a dialog and a sales call from your competitor is just a chatbot away. 

Getting this level of information from customers and prospects and into your sales systems doesn’t just happen. It requires a digital strategy involving person-to-person relationships coupled with intelligent relationship management tools that turn interactions into actionable intelligence.

That doesn't happen by accident; it happens by design.


Mismatched buyer data collection and sales prospecting tools yield poor insights.

A great CRM alone doesn’t guarantee good results. Full buyer visibility and understanding requires a combination of CRM data and the insights and experience of salespeople to generate actionable data and increase efficiencies across the sales organization.

Business environments can change overnight. Last week’s data could already be out of date, and by the time sales can get on a customer’s calendar, weeks can go by. This means our solutions for collecting sales information and our methods of entering and retrieving it need to operate quickly and efficiently to maximize interactions, wherever and whenever they happen.

Gartner research shows that just 24% of companies believe their sales technology implementation is optimized.”

illustration of man holding ipad, with content floating above him.

Behind the scenes, CRMs need to track how your prospects found you, what content they viewed and when, and then create a 360° profile of those collective interactions for easy viewing, sharing, and updating.

On the front end, sales needs real-time information. Often, there’s little time to pull together data from numerous sources in an attempt to see an accurate picture of the customer. Information should be organized simply, attractively, with minimal click-throughs, and with maximum visuals. 

Giving salespeople the tools and data they need to understand your buyers doesn’t just increase the likelihood of closing a deal; it frees up time to close more deals. When sales reps have all the relevant information about a customer or prospect at their fingertips, they spend less time qualifying leads, engaging with the wrong contacts, and preparing for sales calls. They spend more time building relationships with the people who need your products and who have the power to make a purchase decision. And according to a Forrester report on data quality, neglecting to manage your data properly impacts future revenues, erodes customer satisfaction, is detrimental to employee productivity, and can decrease your regulatory compliance.

Once we’ve increased our understanding of both our sales team and our customers, we can turn to our technology stack. Here again, our knowledge of both our salespeople’s habits and preferences, coupled with an understanding of what information we already have and what we still need, guides our sales transformation. 

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1 Bruno, John, Stephen Powers, Meredith Cain, and Peter Harrison. How To Improve Your Top Line With Salesperson-Centric Software. Rep. Forrester Research, 5 Oct. 2016. Web. 30 Mar. 2017.
2 Are ecommerce customer retention strategies working? 2016
3 Top Customer Relationship Management (CRM) Sales Technologies,,
4 Goetz, Michele, Kate Leggett, Josh Bernoff, Leslie Owens, Stephen Powers, Victoria Boutan, Deepti Datta, Abigail Komlenic, and Shaun McGovern. Fix The Data Problems That Destroy Your Customer Effectiveness. Rep. Forrester Research, 18 Feb. 2015. Web. 19 Jan. 2017.