No Matter the Distance: The Best Ways To Manage Your Remote Sales Team

If you work in sales and reading what I’ve been reading, chances are you’re familiar with the benefits of hiring your best and brightest remotely. What’s less talked about, however, is how to manage these types of teams. If you take the plunge and hire salespeople located outside of your office, but don’t know how to manage them well, all of the benefits this type of working relationship can offer can go flying out the window. Luckily, the doom and gloom can be avoided to grow and thrive with the cream of the sales crop.

For the better part of the last 12 years, I’ve had tremendous success working remotely. Through my experience in the “field”, I’ve found the concepts below to be the key ingredients for the recipe of success when it comes to effectively managing a remote sales team.

It All Starts With Hiring

If you want your startup to truly shine in the marketplace, you must hire the best people for the job (regardless of a distributed team). Hiring talent in the “field” allows you to do just that while expanding your reach beyond any given location.

Exciting, right?! But before you pull the remote hiring trigger, you must do your homework and carefully create your “blueprint” for success with a hiring scorecard to keep you on track. Take the time to clearly define your marketplace, buyer profile, what the sales process realistically entails, territory mapping, sales stack to increase productivity while creating efficiencies, and coaching philosophy for starters.

More importantly, do you know what you’re looking for in your next sales hire? Can you articulate the key factors that make said hire truly successful on your team? If you can’t emphatically answer YES with the details to back it up, it’s time to pause and do some soul searching.

For example, I know a well-respected leader that will never hire another person again that isn’t remote. He has seen nothing but massive success and is scaling the mess out of his business. How you ask? Because he knows EXACTLY what he’s looking for, won’t compromise on it, and understands the key elements (trust and an innate sense of accountability are two of several ‘must haves’) of what it takes to flourish on his team.

Hiring the best person for the job isn’t just about the skills they bring to the table, it’s just as significant to ensure cultural fit as well. Take the proper time to ensure you get it right through honest, authentic conversation while trying them on for size can be two effective ways to avoid making the wrong choice.

Set The Stage

I’ve said it before and I’ll say it again, setting the stage early and often has never let me down. Whether your sales team is in-house or scattered across the country, the first thing you should do is discuss expectations for all parties involved. People that work in the field need guidelines they can embrace and follow — just like anyone else you’d want to hire — plan to establish and reestablished early and often.

If you have a mixed bag of an in-house and remote team setup, it’s essential to keep your expectations for both teams the same. Every single person should understand that there’s no inequity between them.

Committed Time Together

One of the downfalls of working remote is feeling isolated or the “red-headed stepchild” syndrome. I would be lying if I said I haven’t felt that way a time or two myself over the years. Scheduling set-in-stone meetings where both of you are committed to the time together is a great way to avoid this dilemma. Whether you need to meet once per week, every other week, or once per month in person, both parties should have a clear understanding of when you’ll have each other’s undivided attention outside of the team huddle. Your time together should be less about your needs and wants and more about your employee’s needs, obstacles, wins, ideas, etc. . Asking meaningful questions and active listening should be your best friends.

It’s also important to set goals along with a shared agenda promoting their growth and ability to thrive (don’t get stuck on sales activity, that’s what your CRM is for). Having agreed upon expectations and goals that are regularly discussed in a meaningful way will help all parties stay focused on the big picture.

I recommend changing it up to avoid the monotony of your 1:1 time together. Requesting an agenda from your employee is a great way to accomplish this while ensuring you keep them engaged and connected reinforcing their important voice. Many times, my boss would blow me off or regurgitate the same topics, never really caring to hear what I had to say or what I/my clients needed and I left the conversation feeling frustrated with wasted, unproductive time. Sadly, I hear about this exact same scenario weekly.

Don’t Go Dark

People in the field quickly become disheartened if they feel out of touch with their team or their manager. To circumnavigate this issue, you should set a personal goal for the amount of time it takes you to reply to slack, email, texts or calls.

Proactively communicating your schedule, when you’re out of the office or going to be MIA is an easy way to avoid this issue. A shared calendar and platforms like slack make life a heck of a lot easier and aren’t difficult to implement.

When you’re managing a remote team, it’s easy to forget about the importance of connecting with the employees you manage personally. There’s such a wide range of tools and technology available that help you stay closely connected with your team, from video to workflow apps to sales technology to conference calls there’s no excuse to create the “island” effect.

Sales technology like ClozeLoop or Jiminny make it easier for you to coach and meaningfully engage while promoting team collaboration to keep your remote sales performers connected, even when you’re not available.

Don’t Be Afraid of Going Impromptu and Unscheduled With Things

It’s easy for people to lose focus after only eight seconds. With that said, it can be difficult for your team to stay on-task and productive (in-house or remote). To avoid this common pitfall, you can connect with the them on an impromptu basis. There is a bit of an art to the unscheduled check-in, though… After all, there’s a fine line between going impromptu and micromanaging.

You hired your team — whether they’re remote or not — because you believed that they were the best fit for the job. Ideally, all of your employees are individuals that take initiative and work well independently, so they don’t need a boss constantly checking in on them to keep them firing on all cylinders.

However, it’s 100% human to become distracted or disengaged, and unscheduled conversations can help everyone get out of that rut. So, how do you help your employees stay focused without micromanaging them? Simply put, you need to listen to them. Let them tell you where they are in their processes and what their buyers are saying. After you’ve heard them, ask them what THEY need and take note to create an action plan that removes barriers while providing effective support. This way, you’ll be hands-on enough that all of your employees will feel truly connected without feeling micromanaged. #winwin

That Wasn’t So Scary, Was It?

Managing a team that’s different from what you’re used to can be stressful to say the least. However, you’ve adapted to change before, and you can adapt to a remote sales team by taking advantage of the insights above. I hate to break the news, but the future of work is through distributed teams.

Although by no means am I suggesting that this a comprehensive list. In my experience, the advice above has proven to be most effective when managing a remote team. What do you think, though? Do you agree that you can overcome the challenges of a remote sales team to realize more advantages than disadvantages? What do you do to maintain great communication and keep your remote sales employees motivated and productive?

I’m excited to hear about how you run your remote sales team. As always, thanks for reading!

In case you’re wondering, I originally wrote this on the Avenue Talent Partners blog.



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Amy Volas

Amy Volas


Helping SaaS startups hire executive Sales and CS leaders without the cringe ⋆ Personally closed $100MM+ ⋆ Founder/CEO ⋆ 2 Exits ⋆ LP ⋆ Sharing lessons here