‘More rewarding for the rep’: Why sales jobs are surging — for those with creativity and empathy

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When it comes to the job market, sales is where the action is. But you probably need not apply for those open sales jobs if you’re not someone who thinks outside the box.

While technology has become an essential tool for the sales function during the pandemic, the real secret sauce is the embrace of creativity as a soft skill for salespeople. In other words, “quirky” is good, said Kris Rudeegraap, CEO of Sendoso, a San Francisco-based B2B relationship-building platform. “Quirky gets attention,” he added. 

As Rudeegraap sees it, a good salesperson is always on the lookout for opportunities to connect — even over Zoom. During a virtual pitch, for example, a rep might spot sports memorabilia in a prospect’s office, then follow up by sending her a StubHub gift card. Or, hear barking in the background? Email that doggy dad a coupon for pet treats.

Even as sales jobs have grown in demand — and in some cases, have come to command generous salaries — it remains one of the hardest roles to fill because of layoffs generated by the pandemic, not to mention the old-fashioned perception of sales as focused on cold calling and hyper-aggressive tactics.

Rudeegraap believes for companies to attract top sales talent, they must distance themselves from ruthless, formulaic approaches and employ strategies focused on building stronger, deeper and more trusted relationships. In his experience, sales teams that invoke empathy and provide a more customized, relevant and creative experience for prospects have scored as much as a fivefold increase in close rates.

The tone of the workplace — in sales, as with all jobs — matters. “A lot of companies are trying to create an environment that’s more open, more rewarding for the rep,” said Rudeegraap. And the old, cutthroat way of doing things simply won’t cut it anymore. The Great Resignation is happening in sales, too, he emphasized. Simply put, reps “are not taking as much shit as they used to. It’s easier to interview than it ever has been. The good companies are standing out that much more from the bad companies.”

There’s no question sales is on fire. In its report “Jobs on the Rise,” LinkedIn ranked business development and sales jobs as one of the four most active areas for job growth in the pandemic. According to LinkedIn, the number of job listings in that category jumped 45% from 2019 to 2020, with New York, Atlanta and Denver among the hottest spots for opportunities.

Granted, the face-to-face engagement that defined so much of sales culture in the past has taken a big hit over the last 18 months. The one constant in sales during the pandemic seems to have been change — and the beneficiaries have been those companies that have warmed to that change, according to a recent report from Deloitte Digital, which argues that a shift in approach to digitally-led experience selling has helped businesses embed themselves in their customers’ operations and improved the sales practice overall.

“The good news is that people who get into sales are driven, creative thinkers who are making the most of remote and digital selling opportunities,” said Tony Owens, president of worldwide field operations at LivePerson, an enterprise software company that builds AI-powered conversational chatbots. For instance, they’ve created personalized video content, appeared on podcasts, and upped their social media activity to enhance their digital presences and catch the right eyeballs. “Sales organizations that support these initiatives — or better yet, provide the training to do it right — are reaping the benefits,” he added.

When it comes to sales, technology — as with so many other functions of business during the pandemic — has been an obvious game-changer. Rudeegraap’s 450-person team has taken to tech tools like the sales-engagement platforms Outreach, SalesLoft and 6sense, as well as Scratchpad, which enables salespeople to easily take notes and enter them in Salesforce.

Technology has, of course, also paved the way for sales calls that used to require travel — and enormous travel expenses for businesses — in a scenario that seems to be a winner for reps and customers alike. 

“The old sales visit you can do over Zoom now,” said Robert Kelley, professor of management at Carnegie Mellon University’s Tepper School of Business, who noted that financial services and delivery apps like Uber Eats and GrubHub have been particular areas for sales opportunities. When it comes to pitches, it used to be that a rep might make two sales calls in a day — one in the morning, another in the afternoon. Now, they might make as many as eight a day, observed Kelley, who predicts that companies will now likely employ a hybrid arrangement of face-to-face and virtual sales calls.

“They’re not spending so much time traveling — that’s a plus,” Kelley said. 

As for the minus? That would be getting on a prospect’s calendar for a virtual call, especially if the delta variant continues to rage. “Zoom fatigue,” he stressed, “is very real.”

“Historically, especially in advertising, so many decisions were made in person, with wining, dining, sports, events, Cannes [Lions Festival of Creativity] — truly decisions were made on relationships,” said Shannon Jessup, CRO at Idealab’s tvScientific, a CTV advertising platform that launched during the pandemic. But with face-to-face impossible over the past few months, priorities have shifted. “Today, relationships are still key, but now differentiation, transparency and performance are the bottom line.” 

And in a world of digital-first interactions, one of a company’s most important sales tools continues to be its most basic assets: its website.

Kraig Swensrud, founder and CEO of sales and marketing platform Qualified, said that in order to make sales personable and effective, it is essential to know when a customer or prospect visits your company’s site, he stressed — and crucial that the company connects with them right then and there. 

“It’s a magic moment when a buyer is showing intent, is eager to learn, and a seller meets them with a personalized interaction,” added Swensrud.


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