5 Reasons Why Technology Isn’t Making Sales Any Easier

Luke Dewall
7 min readAug 20, 2018

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As a software sales professional, I spend everyday talking about how technology can fundamentally make people get their work done easier, faster, with less stress, and with a smile on their face. My sole purpose in my job is to create the vision of what is possible with technology. Regardless of what you sell, you are pitching how you can make something better, easier, faster, or more efficient.

One day while I was researching a prospective customer, I thought to myself, “Why is nobody trying to make MY job easier?”. The evolution of technology has dramatically improved the way people get work done. However, for whatever reason, it does not seem that technology has improved the way work gets done by sales professionals to the same degree. After months of pondering this discrepancy, I have arrived at five reasons why advancements in technology are not actually making sales any easier for sales professionals.

1. Technology is not giving sales reps more time to actually spend on revenue-generating activities

Almost every sales rep will tell you that time is their most precious resource. But a new study has found that sales reps spend less than 36% of their time on revenue-generating activities. The amount of time that we spend on administrative tasks, adding information from our notes into our CRM, travel, putting out “fires”, internal meetings, and researching our prospective customers takes up the majority of our days. How can we be successful when we are only spending 1/3 of our time on actually “selling”? To be more effective, we need to get a portion of this time back.

One way to do this is to leverage AI and Machine Learning to automate the mundane and time-intensive activities that a human should not actually have to perform. Yet, here we are. We are still manually reading through things such as 10-Ks, annual reports, investor presentations, articles, and LinkedIn profiles to gain insights into how to effectively reach our next prospective customer. Let’s not even get started on the time it takes to transfer notes into our CRM. . . With emerging technologies, this is just not acceptable.

2. The solutions being created to “help” sales professionals are being created by people who have never been in sales.

There are thousands of solutions out there that posit themselves as “sales enablement” tools. However, most of them help very little, if at all. When looking across the web for such tools, based on the verbiage and buzzwords used, one can tell that the people that created these tools have never actually been in sales and do not truly understand the biggest challenges we face on the frontlines. For example, we don’t need our CRM system to give us an automated message saying that our opportunity is unlikely to close in time due to the decreasing frequency of activity logged to that opportunity. . . our intuition can tell us that.

One of the most glaring examples for this is that the majority of these solutions focus on stages of the official “sales cycle” (from lead to closure). We all know that an enormous amount of our time and effort is spent before a lead is even identified. Another huge issue is that every company has its own unique sales process and go-to-market strategy for sales, yet the majority of solutions out there are one-size-fits-all. We need technology that is tailored and purpose-built for our specific needs. As sales professionals, we need tools that ACTUALLY HELP US.

3. Solutions are being created for sales management, not for sale professionals on the frontlines.

I cannot argue with the logic in doing this. Sales management is where the money comes from. If someone launches a startup to improve sales, they will never be able to grow that business by relying on individual sales reps to purchase their solution. Therefore, these solutions need to appeal to sales management. However, what sales management wants and what sales professionals need are usually two different things. Sales management cares about improving KPIs, such as increasing conversion rates and decreasing sales cycle duration . Yes, we would all love to increase conversion rates and close more revenue and do it faster, but these solutions are missing a fundamental question, “how can we accurately identify and effectively reach a prospective customer?”.

Often times, when sales management pushes these solutions on their sales force, it adds more work and more complexity to the daily life of their reps. It leaves sales reps with a feeling that “big brother” is even more prevalent. Management gets excited about their shiny new toy, but now their sales reps’ time is spent towards fulfilling a new metric to justify the expenditure on the new tool instead of on meaningful, revenue-generating activities.

4. Technology is trying to make sales a “science”, but sales will always have an “art” to it.

Let’s use an analogy here. Think of how analytics has fundamentally changed Major League Baseball. Hopefully you have seen “Moneyball”, but let’s unwrap this even more. Before analytics, most decisions in baseball were based on intuition. Managers used their gut to decide when to steal, hit and run, bunt, etc. A pitcher and catcher would do some research on batters to figure out when to throw different pitches based on the individual batter’s weaknesses, but was still mostly based on intuition. As analytics has become more prevalent in baseball it has changed the face of the game.

For example, since 2008 the number of stolen base attempts has been on a steady decline. Players have not gotten slower, nor has the success rate changed much. Analytics has revealed that the risk of the runner being thrown out outweighs the benefits of advancing him to the next base. Similarly, in the past pitchers were told by their managers that they should throw a certain pitch more frequently to improve their chances of success, but now they are given a report with hard data that shows that if they throw a certain pitch more frequently they will improve their chances of success by a certain rate.

Baseball is steadily becoming more of a “science”, but there will always be an art to the game. The human-factor is the “art” and that will never go away. Science cannot always trump intuition. A batter can have all of the data in the world about what a pitcher might throw him, but it is still up to the batter to swing the bat. This is similar to how we see technology trying to make sales a science. Sellers can have all of the information and data in the world, but it is still up to the human to take action on that information to close the deal. Your jobs are safe.

5. Too much “white noise” and siloed information

Almost all of the information we need to effectively reach and land our next customer is out there, somewhere. The issue is that this information resides in thousands of different places and we simply do not have enough time to find it. The best sales reps do their homework and find as much information as they can, then intuitively connect the dots between these disparate pieces of information to generate actionable insights. The problem is that this takes a lot of time, experience, and not every sales rep is as good at this as others. To be the best sales reps we can be, we need to get these relevant and actionable insights quickly. However, there are no solutions that are helping us cut through the “white noise” and synthesize this information to set us up for success. The technology to accomplish this is here, but we are not yet the beneficiaries of said technology.

Would love to hear your thoughts in the comments section below or shoot us a note at Contact@RisingTide.ai

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Luke Dewall

Enterprise software sales professional. Passionate about & committed to elevating sales professionals to their full potential. LinkedIn: https://bit.ly/2wFWxNA