014: Building a Remote Sales Team? Avoid These 3 Common Mistakes

The future of work is going to be more and more remote. Not just for designers, developers, and marketers, but also to sales people.

But you can’t execute the same remote playbook that you applied with your remote engineering team—sales is a very different kind of work, and sales people are uniquely different creatures.

There are 3 common mistakes I see again and again that ruin remote sales teams.

Mistake #1: Hiring inexperienced sales people.

Mistake #2: Being too nicey-nice.

Mistake #3: Ignoring the need for social team interaction

In this episode I share how to avoid these 3 common mistakes that ruin remote sales teams.


The future of work is remote. There’s a reason why we decided to build a fully distributed team at Close and why our companies will be remote. But there’s one part of the remote organization that is still kind of a last holdout, uh, a team of department and area in the company that is harder to build in a distributed fashion than other teams. And that is the sales team.

Building a remote sales team is hard. There are many reasons for this, but at the heart of it is that salespeople are probably amongst the most social animals within your company. Uh, probably amongst the most people-centered personalities within your company. And so salespeople enjoy being around other humans. They draw and get energized by interactions with other people.

And to be honest, you know, traditionally a lot of sales teams that were a bit of a wild bunch of people that were high energy but maybe needed a little bit of adult supervision. So traditionally you always wanted to have the sales team. In an office with adult oversight, um, creating an environment that is hopefully healthy competition, but that thrives from interaction between the different salespeople and the entire sales team at large.

So when you try to build a remote sales team, you losing all of that, you are asking somebody to sell day in, day out, designing their own workday. Um, in many situations probably selling from their home or home office. And so most people that would attempt to do sales that way would feel probably disconnected and sooner or later they would find it hard to get the motivation necessary intrinsically in order to perform, um, the job as well as they want to. So. That’s probably at the heart of a lot of the issues.

So I wanted to highlight three quick mistakes that teams make, remote companies make as they’re trying to build their first remote sales team and how to avoid these. But let me just make a statement longterm, which is that:

The future of all work will look more and more remote and distributed. So that will impact sales organizations as well. So since we know that sales teams and sales organizations are going to be more remote in the future than in the past, you might want to embrace it and take advantage of that.

But let’s look at the three core mistakes a lot of teams make when it comes to building and hiring a remote sales team.

Mistake number one is that. This is still an area where it’s probably going to be too hard to hire somebody totally inexperienced and right. So if you want to build a remote sales team and you want to hire people right out of school or college that have never had a professional job, that have never sold, people that may be are high potential and high talent, but that need a ton of training, a ton of coaching, a ton of mentorship. They need to learn how to work in the professional workforce at the same time, how to do sales, and they need to learn the fundamentals and ABC’s of selling and on top of also learn kind of your industry, your buy, your company, your culture, your processes, and then on top of all of that, learn how to be. A remote employee and how to organize themselves and design the perfect work life integration and all that, that’s just going to be too much to handle.

So I would highly advise most remote sales teams to not hire super junior talent, try to hire people that are more mature, that have a track record of being very disciplined. Being very consistent. Um, people that maybe have had a year to three years of sales experience. So they’ve learned the ABC’s of selling. They understand the basic fundamentals of what it takes to be good at sales, and that for one reason or another, either want to travel a lot or don’t want to live in one of the big kind of cities where all the jobs are about for personal reasons or whatever, they want to live somewhere where there might not be that many exciting opportunities for them, especially if they’re interested in tech and in work in the software space. So that’s the type of person you should look to hire.

The second mistake that a lot of remote sales teams make is that they are, you know, are just not competitive enough. Right? So, um, a lot of remote companies, they’re very inclusive organizations. They’re very diverse. They are the type of companies that truly care about that culture and care about their people. So by design, these teams and these cultures, they’re not really that competitive. It’s not just part of that markup. It’s not part of their DNA. Um, the way they’ve built the developer team, the product team, the design team. The marketing team, the support team, none of these teams probably is going to be highly competitive.

Now, when it comes to sales teams, sales teams are competitive and they need to be competitive, to be healthy and to be thriving because salespeople and the best salespeople that are out there, they’re competitive creatures. They want to be compared with others. They want to compete and they want to improve. They want to have a number on the scoreboard that gives them the feedback on how well they do and how well they do in comparison with their peers.

I know that for most remote companies, this will feel toxic, but it doesn’t have to be, right. Um, think about a great sports team that is really a unit where people work together, collaborate and want the best for each other, but also compete. Also compare and want to prove themselves day in, day out.

Um, so that’s kind of how sales teams and the best sales teams in the world are designed. So you want to make sure that within your remote sales team, there is friendly competition. There are comparisons. You use leaderboards, you have monthly, quarterly, yearly competitions that people can win or lose. Where you show feedback loops to the entire company on who is crushing it, who is doing better than others. You can have competitions based on activity or based on outcomes or based on totally different criteria, but you want to create a friendly, but competitive environment and team, even if that’s something that you don’t do in other teams within your business, right? The remote sales team will operate slightly differently than you are the teams that you have to embrace that you can’t just have one size fits all. Kind of, uh, philosophies when you’re trying to build a global remote organization.

And then the third mistakes that remote companies do when it comes to building a remote sales team is that they are. Communicating again with a one size fits all framework of thinking, well, let’s communicate mostly via, via chat, mostly via maybe, you know, online project management tools, online document tools, an email, and do very little kind of synchronous video conferencing, personal communication and, um, when it comes to your sales teams, you do want to do more of that, again, because of the reasons that I highlighted earlier where salespeople are social creatures, so they will thrive and they will like, and it will energize them to see their colleagues, to see their coworkers, to interact with people, see their faces, see the environment they’re working in.

So you might want to do a daily quote unquote stand up zoom meeting, let’s say, where people can see each other, tell each other what they’re planning to do today. And then maybe at the end of the day you have another quick call where people can share. Those kind of wins and losses and how their day went with each other.

We did this for experiment once where we had, you know, especially the sales team, use Snapchat and send each other little video stories when they had a victory or defeat. Anytime they closed the big deal, they would just record a 10, 20 second video, you know, doing a happy dance or ringing the bell in their bedroom or whatever the hell they were doing, and they would send it to others to create that little bit of a social celebration moment to tighten up the fabric of the social markup of the team. Antish to put a smile on somebody’s face and give everybody on the team a sense for how everybody else feels and what their life and day looks like.

So you do want to inject a lot of video communication within your sales team, probably a lot more than what you do with other teams.

And the worst thing that you could do with a remote sales team or remote sales rep. It’s just to give them some kind of a quota of goal and then tell them, you know what? You know, I’ll check in with you again in a month or in a quarter and see how it’s going. That’s never going to work well. Right. This is not a good idea for any team member in any team, I would say in a remote company, but in the past, I’m sure some companies and some people got away with it, especially when it comes to maybe a developer or designer. Um, somebody that could maybe productively work on their own for many, many days and then show kind of a, a work finish, work product to somebody else. But in sales, you really want to have daily interaction, communication, motivation, um, just the ability for everybody on the sales team to feel very close and very connected with their peers in video. Is going to be a big component to making that happen.

All right, so these were the three tips, the three mistakes to avoid and the three things to do if you want to build a successful remote sales team in today’s world.

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