Connor Bush picked a bad time to start a new job as an outside sales representative.
It was May 2020, and he had just accepted a position for the legal software company Gemini Legal. At onboarding, they gave him a stack of fliers, a car and a 200-plus mile territory of accounts in southern California. Since the worker’s compensation legal industry is notoriously antiquated — still relying on faxes and mail — almost all sales interactions were face-to-face, Bush said.
Of course, the pandemic had other plans. While some legal offices remained open his first two months, everything shut down by July that year. As a result, Bush joined thousands of other outside sales reps — salespeople who travel and meet customers in person — across the country in making the transition to virtual sales.
Tips For Adapting to the Future of Outside Sales
- Send a follow-up message after every virtual interaction. This will help you maintain the momentum needed to keep the deal moving forward.
- Recreate your in-person interactions as much as you can digitally. Send a catered lunch for your virtual meeting or schedule a donut delivery for a morning demo to add a personal touch.
- Use video pitches to provide more personal cold outreach. Video recorded pitches can help you stand out to the buyer and simulate the in-person experience.
- Pay attention to vocal inflections and facial reactions during meetings. These can still be useful signals to gauge the buyer’s reaction to your pitch.
- Schedule in-person visits to help clinch a deal. Appearing in person can still be a deal-maker if the parties involved are comfortable with meeting.
The year since has marked a significant shift in both Bush’s career and how outside sales teams operate.
For most of the profession’s history, outside sales (also known as field sales) has been one of the most important ways for a business to grow, according to Dave Egloff, Gartner’s VP analyst for sales. If a company wanted a competitive advantage, it would deploy a team of sales reps across the country to shake hands with their buyers, run demos and close deals. And many of those reps who lived in airport terminals and hotels for half the year wore their road warrior status as a badge of honor.
But the pandemic caused many of those reps to transition into inside sales — a sales strategy where all interactions are conducted virtually — for the year. Now, even as some offices consider re-opening, many sales leaders are rethinking their approach to outside sales.
While Egloff believes face-to-face sales will always have a role to play, a new, hybrid approach is taking over.
Speeding Up a Trend
While the pandemic has been a catalyst for the transition away from traditional field sales, inside sales skills have been growing in importance over the last five years.
Thanks to the proliferation of sales engagement tools and video platforms, reps are able to build stronger relationships and navigate more complex deals virtually. Buyer preferences have also shifted toward a more independent purchasing path, with 33 percent of buyers saying they’d even prefer a rep-free experience, according to Gartner’s Future of Sales in 2025 report.
The report also found that 80 percent of buyer experiences are expected to be digital in five years. As a result, inside sales teams are growing at a faster rate than outside sales teams.
“Buyers are changing, so sellers, like every other business resource and individual, must adapt to the needs and demands and preferences of buyers,” Egloff said. “So you cannot apply 1990s selling to 2021.”
Yet, organizations had been hesitant to give up field sales, Egloff said. While many leaders believed virtual selling tactics (the act of inside sales) could work, it was still an unknown hypothetical.
The pandemic forced those leaders to experiment with virtual selling in lieu of in-person visits. What many sales organizations discovered was that inside sales tactics can work for more complex deals, Egloff said.
A recent Gartner CSO priorities survey of 61 chief sales officers found that 67 percent were either in the process of considering or executing a transition of some field sales roles to full-time virtual.
Still, Egloff doesn’t think outside sales is going anywhere. Instead, the skills for the job have evolved. Since buyers now do most of their product research online and most companies have remote teams, it makes sense that outside sales reps will need to know how to run a virtual demo.
Buyers may even prefer the convenience of a video meeting over an in-person visit.
“Let’s say you have the opportunity to give a virtual demo or you have the option to travel. … In the past you might travel and give the demo to seven people in a conference room. Now there’s two, with others dialing in,” Egloff said. “Even though you’re in the room, you’re still giving a virtual demo.”
That doesn’t mean outside sales reps need to become full-time inside sellers, nor should they, Egloff said. There’s always value to face-to-face conversations. It can help push a deal over the edge and make longer information-gathering sessions more valuable.
“It’s not to say if you’ve been traveling for 10 years and you’ve been successful, you’re losing [anything].”
There’s also a strategic advantage for sales leaders to keep a team of outside sales reps with a smaller book of accounts. Inside sales teams tend to have a larger account list, with some reaching up to 500 prospects, Egloff said. Keeping a team of outside sales reps with a smaller book of business allows them to still give those buyers a more personal experience.
Field reps also tend to have more domain knowledge from visiting enterprise companies, which will help them execute more complex sales.
The only difference for many reps will be that travel is no longer the default. They will need to learn how to execute a virtual demo and build relationships over emails and Zoom meetings. Any in-person meetings will also need to be in sync with the marketing content and research the buyers have already been doing, Egloff said.
“It’s not to say if you’ve been traveling for 10 years and you’ve been successful, you’re losing [anything],” Egloff said. “You’ve acquired sales disciplines, sales skills, points of influence and business acumen. All of those things are applicable. You’re just going to be in less travel lounges.”
Adapting to Hybrid Selling
In the beginning, Colin Specter wasn’t sure his sales team at Orum could be as effective without traveling to visit customers face to face.
His outside sales team included three reps who focused on closing enterprise deals across the United States. Pre-pandemic, the reps followed a typical outside sales schedule. They’d visit one market each week and schedule at least three or four customer visits. During that time, they might take the person they’ve identified as the champion out to lunch, establish a relationship with the decision-maker and run demos of their automated dialing tool with sales teams.
Those trips played a critical role in creating the momentum necessary to close six-figure deals, Specter said. Being in person allowed the reps to troubleshoot and create buy-in among the prospect’s sales team. Meanwhile, stories of reps flying to a customer’s office on the last day of the quarter to push a deal over the edge were common.
While two of the outside reps had experience with inside sales, he wondered whether or not they could create the same momentum with enterprise firms selling virtually. It turned out he didn’t have to worry.
“We’ve actually closed some of our largest deals in company history during this time, and we’ve done it all remotely,” Specter said.
Orum has since transitioned its outside sales reps to a hybrid model.
Under the new approach, the former outside sales reps build most of their relationships virtually, meeting with customers and running demos over Zoom. Travel still plays a role, but only if the customer is comfortable with it and the rep believes it will push a deal over the edge, Specter said.
Reps might still meet with prospects if they live in the same city, but the days of visiting offices in person to run demos are likely over, he added.
“You’re able to logistically work smarter in my opinion and cover more ground. But it is a different level of work. There’s a lot more on your calendar.”
As a company, Orum hasn’t skipped a beat. Specter’s team has since more than doubled in size. It now includes three mid-market reps and one small market sales rep for transactional deals, according to Specter.
Still, the transition has required a few adjustments for the reps. In many ways, Specter said the job is harder for them now. Where reps could visit an office and build relationships with multiple stakeholders in one visit, it now requires multiple emails to book a video meeting with each person.
“You’re having to be more proactive and disciplined about [meeting people]. It’s like, ‘OK, I’m going to send this person a one-to-one message and attempt to schedule a time with them,’” Specter said “It’s not as ad hoc as it was.”
Meanwhile, virtual demos make it harder to read the body language of each participant. In person, the rep might be able to catch an eye roll from the chief financial officer (CFO) or the disinterested gaze of a participant and give them extra attention, Specter said. While cameras have stayed on and the reps can still read facial reactions, it’s still harder to track the pulse of the room on Zoom. They’ve tried to offset that with sending coffee and bagels to teams in a demo, along with keeping an ear out for vocal inflections that signal disinterest, Specter added.
The virtual-first approach also lacks some of the same urgency and efficiency of an in-person visit. Specter believes the sales cycles can be longer as a result.
Still, the advantages are hard to ignore. His reps can work more deals, spend less time on the road and have the flexibility to decide when they need to be in person.
“You’re able to logistically work smarter in my opinion and cover more ground,” Specter said. “But it is a different level of work. There’s a lot more on your calendar.”
Specter doesn’t plan to put a cap on travel, but he coaches his reps to consider whether the size of the deal offsets the quantity they could work virtually. In short, he doesn’t consider hybrid sales a dispute of field sales. Instead, he treats virtual selling as equal to in-person sales tactics.
Learning New Strategies
One of Bush’s favorite things about outside sales was how fast everything happens.
There’s an art form to reading someone’s body language and pivoting your pitch on the fly, Bush said. You’re able to meet with multiple buyers at once and, when everything goes well, close a deal in a day.
Inside sales require a more methodical approach.
While Bush had some experience with inside sales at a past job as a rep at a software-as-a-service (SaaS) logistics company BlueGrace Logistics, he still relied on in-person visits to close deals. Still, that experience proved valuable when Gemini Legal transitioned to full-time remote.
“Instead of looking at the parking lot, you’re going to look at their LinkedIn, you’re going to leverage ZoomInfo and find social media to make that initial outreach not so cold.”
The transition wasn’t smooth at the onset for Bush and his peers on the sales team. For starters, their customers weren’t ready to go digital. A lot of lawyers were so used to fax machines and in-person interactions that they didn’t even have their own email addresses, Bush said.
Before the team could run video meetings, they’d have to walk the lawyers through setting up Zoom. Bush even met one customer in a parking lot to help them download and set up the video software from the safety of his car.
But the reps also had to learn a new sales approach. One of the biggest adjustments for Bush was how long it took a prospect to get back to him to close a deal. In field sales, you’d get an answer within one or two visits, he said. With inside sales, he had to learn how to follow up with customers after every exchange to maintain momentum.
“A harder pill to swallow was how out of sight, out of mind you are from an inside sales perspective,” Bush said. “You could send someone a contract and they’ll say, ‘I can’t wait to sign this contract and get it back to you.’ That could be months. In person, if you bring a contract and the buyer reads it and likes it, they’ll sign it right there.”
Bush also had to adapt his pitching style.
In person, your relationship with a person is defined and unique, Bush said. You can pepper your pitch with jargon and turn it into a longer conversation. In inside sales, his cold emails needed to be more concise to fit entirely on a phone screen, where the buyer is likely to be reading it. And if he was sending it to a general company inbox, the message also had to resonate with a wider audience.
Of course, some outside sales skills worked to their advantage. Since the worker’s compensation legal industry valued lunch meetings, they’d often send catered meals for their virtual meetings to recreate that experience. They also found that video pitches resonated more with buyers because it was more personal than email, Bush said.
Outside sales reps are also masters at identifying personal details like photos on a person’s desk and using that to create an instant bond. While the sources for personal information are different, the same skill translated to cold calling, Bush said.
“We found that a lot of reps [on our team] were good at making cold calls, not so cold,” Bush said. “Instead of looking at the parking lot, you’re going to look at their LinkedIn, you’re going to leverage ZoomInfo and find social media to make that initial outreach not so cold.”
Gemini Legal’s reps and its customers were excited to transition back to in-person sales as soon as it became viable, according to Bush. Even as the company transitioned back to traveling, skills like sending a handwritten letter to stay top of mind after a virtual meeting have carried over to field sales.
“The transition forced us to add to our toolbelt and toolkit,” Bush said. “I think most of the team would agree that we became better salespeople because of this.”
Embracing the Future of Field Sales
If there’s one positive from the past year of inside sales for Bush, it’s that it has made him a more well-rounded salesperson.
He now knows how to build relationships and close deals virtually and in person. That experience gave him the confidence to pursue and accept an inside sales role for Instawork, something he wouldn’t have done in the past.
“It made me a better salesperson and more confident in my abilities,” Bush said. “[My new role] involves more intense outreach, more demanding quotas. Once I developed and refined my inside sales skills, I believed I could attain that.”
“I can be more amphibious. I can do inside sales, I can do outside sales and I can pull each tool out as I need it.”
At Orum, hybrid sales has been a natural fit for the sales team. Some of his sellers are itching to get back on-site, and when travel is safer, they’ll have that option, Specter said. He wants his reps to have the autonomy to choose when they travel, but he does encourage them to consider the opportunity cost of traveling.
“When you’re traveling and on-site, you’re fully committed to that account. If that account is a half-million dollar contract and the opportunity cost is that you missed out on working a $100,000 deal here or there, I’d rather you work smarter not harder,” Specter said. “My reps have the autonomy [to travel]. At the end of the day, it’s up to them.”
Inside sales skills will likely continue to grow in importance within field sales. The days of reps spending 40 percent of their time on the road are over. Companies will continue to put a higher threshold on travel, which means reps might only travel 10 to 15 percent of the time, Egloff said.
For Bush’s part, he’s ready for whatever the industry demands of him.
“I can be more amphibious,” Bush said. “I can do inside sales, I can do outside sales and I can pull each tool out as I need it.”