What is the secret to remote work? Just ask your Sales team.

Published in

Austin Startups

6 min readJan 2, 2021

The world has changed.

The charlatans are at the gate; the bloggers are salivating, and everyone’s trying to make a quick buck. The hype cycle for “Remote Work” and “Distributed Companies” has reached a fever pitch, and everyone has an opinion about it.

Meanwhile, Sales and Customer Success teams are plugging away, working remotely, as if nothing has changed. Because for them- it’s business as usual.

Let’s take your standard Enterprise Client Partner, who manages a $3M book of business with 20 Accounts. For years, she has been pulling dollars from the sky with a phone and email address. Meanwhile, we have bigco tech employees complaining about not getting their free food delivered to their apartment in Noe Valley.

Sales and Customer Success teams have been “working remotely” for years with the most important people in your company… your customers.

I’ve had the opportunity to work with some of the best Enterprise Account Executives and Client Partners in the business. I witnessed them close million-dollar deals remotely over phone/email and manage massive books of business with clients they visit in person once, maybe twice, each year.

Here are some lessons I’ve picked up after watching them work with clients distributed across the country, which should be adopted by leaders of a newly remote workforce.

Set up your communication lines to be consistent and predictable.

The best Salespeople have regular and comfortable communication with their Accounts. There is always a next meeting on the calendar, and between meetings, they build informal communication lines (often over text) with critical decision-makers and influencers at the Account.

Here is the lesson for remote leaders: Build a clean schedule of regular meetings and 1:1s, each with a clear purpose and updated agenda. Foster a culture that also encourages un-scheduled, informal touch-points.

Individuals at your company (like clients at an Account) should be comfortable deciding if a topic should be brought to the next meeting or discussed immediately. Like an important client, your team should never question how/when/if they should communicate with you.

Take it off email (and Slack!)

Capable Client Partners know that if an email chain is starting to balloon, it’s best to jump on the phone with your contacts at the Account and sort things out; otherwise, items are taken out of context and things go south.

The lesson for remote leaders: Take the lead in encouraging a quick call when email/slack conversations are dragging on without progress or if things get heated. Ensure your communication stays strong by moving fast, communicating transparently, and following the principle of debate and commit. But remember that these types of conversations should be done live, not over email/slack.

Be prepared for meetings.

Meetings are an important medium for people to brainstorm, debate, and decide.

Salespeople place enormous value on every meeting with a client. They acknowledge how difficult it is to get all the right people on a call and secure time on a client’s calendar. They always come prepared.

The lesson for remote leaders: Take your meetings seriously. In a distributed environment, work is often solitary. Team Meetings are a unique opportunity to bring a team together. 1:1s play a critical role in keeping relationships healthy.

Ensure everyone participating in a meeting has the opportunity to contribute to and review the list of topics in advance. Nail the meeting’s technical elements by getting things set up early, so when it’s time for the meeting to start, you are ready to go. Don’t reschedule meetings and 1:1s.

Finally, just as a great Salesperson checks in with their Account to ensure they are getting everything they want out of their meetings, remote leaders should do the same.

Recap!

Salespeople know that things can get a little scattershot during remote meetings. Therefore, they always send out a precise recap email (within 24 hours) that outlines the topics discussed, the decisions made, and the next steps for each individual and the group. They also encourage the client to respond and share their perspective and contribute any critical notes not included in the recap. The recap email is an essential step to ensure alignment and continued progress between meetings.

The lesson for remote Leaders: With Slack’s rise and the disconnected nature of distributed work, employees and companies often share partial information without context and clarity. To combat this, distributed companies should document everything. Documentation ensures everyone understands the context and priority of their work and helps teams stay aligned..

You may have noticed it isn’t easy to discuss and make strategic decisions over Zoom. Leaders should help to facilitate a deep understanding of a topic and a healthy debate by requiring the preparation of written proposals in advance of critical discussions. Read how Bezos applies this approach at Amazon.

Lastly, Leaders should mimic the approach of Salespeople and ensure shared documents are updated after important meetings and expect everyone at the company (not just Leadership) to contribute. This level of documentation and participation may sound like a lot of work but pays off in the long-run.

Remember, people are less likely to feel lost in an office setting, where small-talk and informal communication helps keep people on track. But with remote work, people are sometimes left staring at their monitor, alone and feeling unsure. Days may pass until they feel comfortable reaching out to voice their confusion.

To avoid this, document and recap, just like your Salespeople have been doing for years.

Invest time in relationship building.

Great Salespeople are great relationship builders. This is true, but I can’t entirely agree with the assumption that this comes naturally and with little effort.

In practice, managing a book of business with dozens of accounts spread across the country, and simultaneously building relationships with hundreds of contacts requires dedication, focus, and confidence. It’s hard work.

Salespeople invest time in getting to know their contacts and, from there, invest time in building a relationship. They leverage email, text, phone, and snail-mail to connect 1:1, outside of group settings. They steal a couple of minutes at the beginning or end of a call to connect personally and find areas of common interest.

The lesson for remote leaders: Take time at the top and bottom of meetings to connect with people. Build relationships through one-off unscheduled calls and texts with your team. Be an active listener to find areas of interest and topics where you can build a connection. Occasionally, drop something in the mail, such as a thank you note, or small gift, to bridge the online<>offline gap.

In an office setting, working relationships can develop naturally and slowly over time. A higher baseline of trust exists within in-person relationships. In today’s remote world, leaders must be deliberate and invest additional time into building “remote” connections.

Don’t forget the value of getting together in person.

Enterprise Salespeople work hard to schedule and organize their client visits; knowing the relationship built in-person will help solidify and strengthen the partnership until their next visit. They understand the unique value of meeting in-person and with only 1–2 visits per year, they are strategic about making the most of the time.

The lesson for remote leaders: Think carefully about how often you plan to meet in person and what you hope to accomplish during those visits. Plan them meticulously and ensure you are well-rested and prepared to maximize the time to build your relationships- and have fun!

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