Remote Work Chat #1: Finding Freedom While Hitting Sales Goals

In this remote work chat I ask my friend and past coworker Adam Schaechter about his sales role at the remote-first company Postscript, an SMS marketing software provider for Shopify.

In this conversation about working remotely, Adam and I talk about:

  • How to find full-time remote work in sales without using job boards
  • How to travel the world even if you have to work in certain time zones
  • How to balance the freedom of working remotely with hitting sales goals

You can listen to our full conversation here or read a summary of our conversation below.

Note: This conversation was recorded in October 2019 but is still relevant for today, with the exception of some information related to traveling and socializing that’s not currently recommended due to COVID-19.

Remote Work Sales Q&A

How did you find this remote work opportunity?

Adam did not take the traditional route. While he was working at a non-remote company his friends were building a company that they wanted to be a remote-first organization. When they posted a job for an account executive, Adam reached out to them. It was a good fit and he got hired!

Takeaway: Stay in touch with friends and don’t be shy about asking them about work opportunities.

Why did your friends (the cofounders) want to start a remote-first company?

They wanted to live in two different places so it was the logical choice. And making this choice opened the door to many other great opportunities, like hiring people not based on where they lived but on how good of a fit they were for the company.

Takeaway: You don’t need to live/work in the same area as coworkers to create a great company.

How much travel freedom can you have as a remote worker in sales?

Generally speaking, you can live anywhere as long as you’re in a similar time zone. For instance, if the company’s target market is in the United States, you can live in Canada, South America, or Central America and still be in a similar time zone. Technology like Zoom, Slack, and other remote communication tools make this possible.

Takeaway: Being in a similar time zone as the company’s target market does not mean you have to stay in one place. There are many different travel-and-work opportunities.

How do you handle working outside of a social office setting?

Being in sales makes this less of an issue because you are still speaking with and seeing people (on video calls) throughout the day. That said, Adam goes to the gym, walks to the store, and grabs dinner with friends on the weekdays. It’s easier to slip into episodes of isolation, but when you feel it happening, you can quickly do something about it.

Takeaway: If you don’t want to be isolated, you don’t have to be. There are many opportunities to be social as a remote worker.

What are you doing with your extra time as a remote worker?

Because he doesn’t have to commute and be in the office at a specific time, Adam has more time and opportunities to surf and do dawn patrol. For instance, he will find a new place to surf and, before going, will do some research on remote-friendly coffee shops in the area. He’ll spend the first half of his day at the coffee shop and the second half at his home office.

Takeaway: Replace the commute with something you love doing.

How challenging it is for someone in sales to acclimate to working remotely?

It takes a lot of self-discipline. You need to find a routine and schedule that works well for you and be consistent. When something isn’t working, follow the process of trial and error until you reach a point that allows you to make the remote life exactly what you want it to be while still being able to get your work done and meet your target numbers.

Takeaway: Keep adapting your work style until you find a schedule, routine, and balance that allows you to get your work done and take advantage of the “remote life” at the same time.

Is there an opportunity to be lazy as a remote worker in sales?

Not really. You are tied to a number and need to schedule and attend calls to meet that number. There’s also a lot of transparency provided to teammates through tools like Salesforce that show if you’re on track to meeting your goals. Things are recorded and tracked. The numbers either go up on the board or don’t.

Takeaway: If you’re passionate about not only meeting your goals but helping grow the company, “slacking off” will never become an issue.

Do you ever feel guilty about not working traditional hours?

Sometimes Adam wake up at 5:00 a.m.for calls with prospects living on the east coast of the United States (he is in California). When this happens, he shifts his schedule around in a way that creates a “broken up” work day, or a day in which he’ll stop working earlier. As long as he takes responsibility for hitting his goals and helping grow the company, he doesn’t feel guilty about having an untraditional, flexible work schedule.

Takeaway: If internal communication is clear and there are set goals, you can shift your work style and schedule around in a way that makes you happiest and most productive.

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