The promise of remote sales

There’s never been a better time to challenge the orthodoxy that a sales rep needs to live in the same geography they sell

When someone asks “can our sales team work remotely?” they are posing a rhetorical question to which they believe the answer is no. It’s a superficial question born of puerile thinking; the premise of the question has long been settled. We already know that sales reps can work remotely. They’ve always done so when they’ve traveled. They’ve proved it’s possible throughout the pandemic.

From any one customer’s point of view, most of a rep’s job has always been performed remotely—via email, phone, text, and DMs. This is not to discount the importance of occasional in-person facetime or the value of a shared meal. However, there must come the recognition that one can achieve these things without living full-time in a particular geography. After all, don’t many small- and mid-sized suppliers and importers successfully build their businesses without having an active agent in the market all the time?

Can our sales team work remotely?” is just a way of avoiding the thornier question: “should our sales team be allowed to work remotely?”

This is the question managers and executives are afraid to ask.

Should is a scarier question than can because it admits the possibility of being able to do things differently. Should forces leadership to make difficult decisions and break with normative ideas about how business is conducted. Can denies the plausibility and practicality of making a change. Can tries to absolve the decision-makers of responsibility. When someone asks “should our sales team work remotely,” they confront the real issues at stake:

  • Whether or not a company values its employees

  • Deep-seated fears about what constitutes a meaningful business relationship

  • Operational weaknesses from failing to evolve beyond iterant methods of peddling

When these matters are properly addressed, the only outstanding question is “why didn’t we adopt remote work policies earlier for the sales team?”

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Valuing employees

From a sales rep’s perspective, the ability to work remotely is ideal. The flexibility inherent in this model allows for a better work-life balance.1 Zero-sum thinking would have employers believe they’re giving up something by allowing salespeople the option of remote work. This is a fallacy. When employers adopt remote work they gain the ability to attract top talent that might not reside in the vicinity of a territory.2

The adoption of remote work policies also has the advantage of placing more of an emphasis on the skills a rep was hired for—selling, providing top-notch customer service, problem-solving—rather than commuting, organizing a day around samples, or waiting in line for an appointment.3 Remember, busyness is not the same as productivity.

How meaningful business relationships are formed

The frequency with which a salesperson sees a customer does not indicate the strength of their relationship. Willy Loman, the archetypal peddler from Death of a Salesman, was constantly on the road to seemingly little avail.

Business relationships don’t require the same ingredients—intimacy and passion— proposed by theories of love. While love usually requires physical proximity, business can thrive in its absence given reliable broadband.

Business relationships are built on:

  • Shared trust

  • Being mindful of a client’s attention

  • Empathy and an understanding of each party’s needs

  • Mutual respect

None of these elements requires a salesperson’s physical presence.

Addressing operational weaknesses

Historically, the willingness of iterant wine and spirit salespeople to be “on the road” provided a lot of stopgap solutions to operational challenges—from dropping off samples to picking up damaged bottles. While these practices worked well enough in the past, they currently hobble the industry’s evolution.

The stubborn adherence to old systems unnecessarily casts new technology in a negative light. If a rep is expected to drive from account to account, a text or email from an account is a hindrance. If a rep is expected to commute to accounts on the subway, the loss of internet connectivity while underground is a burden.

For technology to be embraced as time-saving and productivity-enhancing, it needs to be framed as a ballon rather than an anchor. In practice, this means that old methodologies need to be retired.4

The pandemic has opened our eyes to the possibilities of doing work differently. Lack of imagination and courage should not prevent us from pursuing sales models that are different from those of yesteryear. The future promises that it can be better than the past. The freedom for salespeople to be able to live and work in different places is part of that potential.



A “better” work-life balance still plays to the notion that balance can even be achieved. As Scott Galloway tweeted, “Balance is a myth. There are only trade-offs. Having balance at my age is a function of lacking it at your age…”


As Marc Andreessen writes, “Permanently divorcing physical location from economic opportunity gives us a real shot at radically expanding the number of good jobs in the world while also dramatically improving quality of life for millions, or billions, of people.”


But what about samples and in-store tastings? Use surrogates.


The obviousness of this fact fails to explain why so many companies still have fax numbers in 2021.