My father has been an outside field sales rep for over 40 years. For the past four decades, he has loved waking up each day and planning out where to go that very morning.

There are no weekly or monthly planners, no special apps, and no Google calendars booked full of appointments. He relies on his gut and years of experience to intuitively know what needs to be done.

And he is not alone. Field sales is an adventurous and freeing career. Many reps are attracted to its freedom and their ability to become successful on their own.

Yet, the past year has drastically changed the landscape of outside sales. Many reps found themselves trading life on the road for a home office and face-to-face interactions with back-to-back Zoom meetings.

Now that the world is slowly transitioning back to normal, what will the future of field sales look like? With the new advances of technology, new ways of learning to forge connections and sell at a distance, what will remain and what will change?


The Current Landscape of Sales: Resistance to Change


To understand where outside sales is going, it’s important first to look at where it is and why it is where it is today.

My father embodies what most outside sales dream of and what draws them into their career. Even though he belongs to a different generation of sales reps, his career still represents Millennial and Gen Z salespeople's aspirations. In fact, it is more appealing to younger generations that loathe being chained to a desk and forced to comply with standards and rules that don’t make sense to them.

Outside sales means no micromanagers and no excessive oversight, just freedom, and intuition.

This attraction to freedom is one reason why field sales teams are hesitant to adopt the new software and technology available to them. They worry that it will instead become like another boss, taking away their ability to make decisions on their own. Autonomy is what draws them in, and they shy away from anything that might take away from their ability to move freely.

However, this can hold back many sales reps from achieving their sales goals. While my father may be the dream and standard, not every salesperson has 40 years of hard-won experience to rely fully on their gut to make the right decisions.

Another challenge to technology adoption is that field sales is heavily relationship-based. When you compare inside and outside sales, it is one of the most critical distinctions. While inside sales is 95% science and 5% art, outside sales is 50% art and 50% science. This difference helps explain the contrast in technology adoption.

Inside sales is a numbers game. If they can make hundreds of calls or send thousands of emails a day, they can drive more sales. That is why they are quick to pick up any new software that fuels their efficiency: impersonal technology that increases their reach is more likely to succeed.

The target audience for field sales, on the other hand, loves buying from other people. It takes building trust and an underlying relationship between the prospect and rep. In the end, face to face sales reps beat the competition through the strength of their relationships.

Much of the sales technology over the past few decades was not geared towards the needs and challenges of face to face sales. Instead, they resulted in more leadership oversight and did not encourage the trusted relationships reps needed to succeed. Plus, many of the best prospects in certain industries don’t have an online presence yet, making much of the technology previously available useless.

However, the software of the future has these challenges and needs in mind to help outside sales reps become more successful than ever.


The Future of Sales: Data-Driven Autonomy


To say the past year was challenging for outside sales is an understatement. Social distancing forced many field reps to become creative to keep earning a paycheck. They had to find ways to build and maintain the critical relationships to make sales from a distance.

Depending on the industry and company, COVID affected reps in one of three ways:

  • Hybrid selling where reps traveled less and spent more time in their home office
  • Completely suspending all travel and in-person contact
  • Or traveling even more to meet demand

Salespeople had to become more careful and judicious than ever. Traveling and in-person contact started to carry more significant risk, so they had to decide when it was absolutely necessary.

This shift forced field teams to embrace technology at a rate they never had before the pandemic. Without the use of software, they couldn’t make vital sales. As a result, reps began to embrace digital communication at every part of the sales funnel. Data helped them become more strategic about traveling and when to push out to new territories.

The result of the pandemic has driven the adoption of data collection for outside sales.


Increased Data-Driven Insights


The future of sales, then, is an increasing embrace of data to help drive flexibility in and out of the field. Many sales teams found that collecting data didn’t detract from their autonomy or force more leadership oversight. Instead, it allowed reps to make more informed decisions.

Sales teams now have the knowledge that usually takes years of experience and potentially costly missteps to learn with the help of data. They can glean insights into when and where they should be spending their time. Reps can figure out which prospects have the best ROI and what areas should get more of their attention.

Before, it typically took leadership to get these big-picture insights, but now reps can gather vital information independently. Now they can experience more autonomy and freedom than ever.

The newest technology for outside sales position reps to be more effective with their time. This way, they can concentrate on the vital parts of their job: building trust with potential customers. Instead of getting in the way of relationship building, outside sales software will give them more freedom to actually concentrate on the parts of the job that matters.

All of this will result not only in reaching goals but actually make sales more fun. No longer bogged down with chasing dead-ends or endless spreadsheets, they can concentrate on the thrill of getting new customers.

Some of the things that field sales software, like Map My Customers, can do for reps include:

  • Apps to help create smarter weekly schedules
  • Pulling data from customer cadence or leads gone cold to make phone calls easy during previously wasted time, like a long drive home
  • Heat maps of revenue and sales activity
  • Data autofill to reduce paperwork

These activities allow reps to fill their pipeline and hit their quota while still maintaining their freedom.


The Winning Sales Team of 2025: Data-Driven, But Not Data-Only


In the next few years, teams will become data-informed and data-driven, but that doesn’t mean that they will become data-only in their sales approach. Building relationships and trust is still at the heart of sales, and the 50/50 mix of science and art will reign.

Face to face sales is successful because it relies on the art of selling. Technology will encourage it, rather than trying to over-analyze sales and make it mostly science, like inside sales.

Instead, this technology increase will free reps from dreaded spreadsheets and business cards that they have used for far too long. It will also enable sales teams to be one step ahead of the competition with increased insights and reduced paperwork.

Sales teams of the future will be able to intelligently gather information to make their own decisions. The relationship between technology and outside sales is a lot like making a cake. Outside sales software acts a lot like the raw ingredients. They have a lot to offer but don’t do much on their own. Sales reps use these ingredients and mix them in the way that they feel is best.

Field sales software like Map My Customers gives sales teams the information they need to make vital decisions for reaching prospects and growing their territories. Data gives teams more control because they have all the information they need available to them.

Sales teams are still in charge and make decisions. Still, technology can give suggestions that may not have occurred to anyone and a better understanding of what is going on in their territories and industry.


Step into the Future of Outside Sales


Many sales reps who tried to build their careers like my father failed because they lacked his keen intuition and years of experience. Without understanding what was going on, they wasted their time in the wrong places and activities and failed to build the relationships critical to success.

However, technology is now making that dream more accessible to salespeople than ever. They can be in more control than ever, and leadership can more comfortably let sales teams have the autonomy they crave.

The insights and increased efficiency allow reps to focus their attention on the part of their job that matters: selling.

As we emerge from the pandemic, it’s time to enter a new era of outside sales. Are you and your team ready?