What It’s Really Like to be Part of a 100% Remote Sales Team

I was sitting at a networking event (pre-COVID-19) and the question came up about remote teams and whether it was good for the sales profession.

One CEO crossed his arms and said, “We would never do that! Building sales teams at scale would never work. I need everyone to be in the office in order to be productive. How do you know what they’re doing if they aren’t?”

“Thank God he’s not my boss,” I thought.

Baffled by his response, I explained in intricate detail how we did just that.

While remote work is certainly different than what we’ve known as an industry for the past thirty years, I would like to challenge the prevailing view that productivity in the modern age means being in a physical, often open office environment.

Even though one CEO didn’t respond favorably, I realized that all the other leaders at the table were either asking me numerous questions or rigorously writing notes on how we successfully scaled an entirely remote global sales team.

They were eager to learn more. I was happy to oblige.

I lead the revenue team for Chili Piper. This is my remote working experience.

Many of the responsibilities I have as a manager today are very similar to my duties in previous roles. I have meetings. I have a team. I train. I coach. I hire.

The fundamentals are the same. So why do I prefer managing remotely over in an office?

Let’s start with the backdrop of my own experience before I get into the tactical management aspect.

I have an eight-minute walk to my coworking space instead of the formidable-in-comparison 45-minute drive each way to and from the office. I come to the office when I want to, and when I do, I’m refreshed and ready to go.

This is where I occasionally work in Oakland, California.

I’m not artificially driven by a predetermined time dictated by someone else as to when I must arrive.

Many days I work from home, or a coffee shop, or a friend’s office. For me, this sparks creativity, reflection, and problem-solving, something I think many businesses are severely lacking. The rigidity of it all is boring and tiresome. It’s not holding the attention span for millennials like myself.

Remote work allows me to be ultra-productive, while also prioritizing self care, creativity, and innovation.

For me, remote work harks back to the most productive time in my life — college. I was able to have some structure of classes a few hours a day, but overall my time was free for me to decide how to spend. It comes from the belief that we are most productive when we’re given freedom to think and work in a way that best suits us.

Mental health is a real thing in sales. Something that’s been largely ignored, especially for managers. Most managers are so focused on the tactical execution of the mission that they forget they’re managing people as well as their own well-being.

Working remotely enables me to focus on myself first, which allows me to be much more empathetic and helpful to my team. When I show up, I’m fully in the present. I’ve meditated, read, exercised and prepared a healthy meal. I show up happy and ready to get sh*t done.

Being engaged in activities outside of work fuels my creativity and innovation at work. I have more meaningful connections now. All of this makes me love what I do as a leader. This is what it feels like when something is “right” for you. I was a skeptic of this initial setup at first, but now that I’ve been working this way for over a year, I can’t think of working any other way.

When setting up my team – I can hire remotely. I have access to a global talent pool and it’s been a remarkable advantage for building my team. When I started my present position, I left a larger company with a big team for a team of one person–me. I had to figure out where to start from scratch and I was alone in doing so.

Remote Work for Sales Reps and the Importance of a Personal Brand

My biggest piece of advice is to immediately start building your own personal brand. Too often people wait in this area or never get that started. You can start today. Hell, email me and I will tell you how to do it, even if you’re fearful.

Your personal brand online and offline will fuel your ability to hire the best possible talent. The number-one reason people still join companies and stay there is because of the company’s brand.

But why are you waiting to build your brand? It’s a long-term investment but it has been the most critical thing I have ever done to build a team. My traffic is entirely inbound because I push messages to the public that is enticing to employers and then our company delivers on that when they work here.

You have to be seen as an expert delivering a massive public reason why people should work with you. For me, that meant building a presence on social media, something I did from scratch. Fast forward to today, we have 40 applicants per day applying for a multitude of roles all across the globe and I cherry-pick from the best candidates among them.

Meanwhile, my friends in LA, NY, and SF all ask me how I find the best candidates. They are confined. I am free.

Remote Work for Sales Teams: Keeping Your Team Productive

Now that you’re in a better personal state and have a great influx of talent coming to you, next is the hard part. The day-to-day management.

This is where people really fall down.

“How do you know what your team is doing all day?”

Okay, big brother.

For those that have managed regular, open office, in-person teams, this is usually a tough one. I still have the urge to “walk over to someone’s desk” and show them how to do something. But not being able to has forced me to communicate what I need more precisely. Working remotely has also eliminated unnecessary meetings.

I don’t sit on my Zoom meeting all day chatting about nonsense like I would walking to and from meetings in an office. The meeting starts, I get to the point. It ends, I go back to working.

I still do all the things I did before. I have weekly standing meetings. I have 1-on-1 coaching, sales training and meetings. I have remedial sessions with people who are behind. I have crazy back-to-back days and more chill days.

I can better focus on what is always my number-one goal: getting them to the next level in their career and being an agent of change within the organization. Exactly the same as before.

The only difference is now I have the same amount of time to work with the team, but I have more time to focus on problem-solving on the critical items that will move the company forward.

So, to answer the question of what my team is doing all day, my answer is simple: if you can’t trust your team to work remotely, then you should never have hired them to begin with, whether they work remotely or not.

That falls on you as the manager for not building a proper hiring machine, not the structure of how people work itself.

The Importance of Communication among a Remote Sales Team

I will say that we do make a concerted effort to create awareness on the sales team. Awareness of best practices. Awareness of pitfalls.

One way we do this is a self-scoring system of sales calls. After each prospecting and discovery calls the sales reps score themselves on a scale of 1-10. That score is then sent to management and we can compare the two and address discrepancies.

This practice has been one of the most invaluable tools to actually move the dial and create awareness of performance. The only thing is by working remotely, they aren’t forced on the how, but rather the result. Autonomy is still king.

It’s been 18 months since I first started with no team. We now have 10 sales people who produce, grown revenues over 150% and have a dynamic company with all the same functions and interactions.

Remote Sales Teams — It Truly Works

Saying remote teams don’t work is like saying vegetarian diets don’t work. Millions of people are thriving on them.


To be fair, some people are not meant to work remotely. We’ve certainly encountered this at Chili Piper and we encourage them to find what makes them happy.

If this is not a fit, we don’t force it down their throat. We want each person who interacts with our brand, whether hired or not, to walk away with the best possible impression of us and hopefully have improved and learned something having had that experience with us.

This setup is not for everyone, which is why we don’t hire anyone. It must be mutually beneficial. However, my belief is that the majority of people, when given the freedom of choice — to decide how and when they work — are better off than the outdated, outmoded open office, forced work structure of the past.

Allowing people to choose how to show up is the first step of autonomy. Autonomy is the first step to commitment and commitment breeds loyalty and high achievement.

So maybe that one CEO was correct to have folded his arms in disagreement with me. Working remotely isn’t for everyone. But the rest of the leaders at the table seemed to think otherwise.

Here’s an interview that I recently did with SalesDevSquad, discussing how I develop and manage a remote sales team.

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