Training new remote sales rep is no easy feat. Any small business owner, recruiter, or solopreneur who has done it will tell you the same thing. 

The truth is, we all have war stories about a remote sales rep we wish we never hired. You know, the one who talked a good game but never did any work. Or the one with expense reports longer than their sales sheets. We’ve come across these folks in brick-and-mortar offices. When they’re remote, the situation can be even harder to monitor.

The thing is, we’re not here to dwell on disappointments. We’re here to turn the bad experiences into useful learning lessons. Without any further delay, let’s jump in.  

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Laying The Foundation For Training New Remote Sales Reps

Can you think of a time that you hired a remote salesperson and it didn’t go so well? Surely, there were reasons to blame the salesperson. However, if you look back at the situation objectively, were there things you could have done better?

Some sales managers think training new remote sales reps goes like this: 

  • Having a 10-minute convo on Zoom
  • Emailing the rep them a bunch of links to motivational videos
  • Throwing them into the job, then deciding they’re not cut out for it when they don’t make any sales 

I empathize with the sales manager in this case. Why? For one, in our discussion, they are a busy entrepreneur that doesn’t have much time. Two, they may not be aware of how having a flimsy training process is affecting their business.

The bottom line is, training new remote sales reps requires structured planning. Without a good foundation, most new hires don’t thrive. 

At our company, we manage our training process in stages. We can describe them loosely as:

Background on our company

The in and outs of the position

Intro to our systems / technology

Training through instruction

Training through observation

Hands-on training



I would love to say we’re perfect and that our training goes as planned every time. Of course, it doesn’t. And here’s what we’ve learned. No matter how great our team members might be, if we don’t set the right foundation from the start, the results just aren’t as good.

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Positive-Attitude Ingraining Culture

A positive attitude is often a defining factor when it comes to success. As a hiring manager, you can’t change someone’s attitude. What you can do set a good example and a tone of positivity that catches on. You can cement positive reinforcement into your process of training new remote sales reps. 

All of this will make it easier for them to receive your instruction and gain the confidence they need to excel.

Plan for Continuous Learning

Once your remote sales rep makes it out of training, don’t expect to stop there. Maintain an open forum for sharing new information and best practices. Training new remote sales reps for long-term success also means setting expectations for planned and un-planned learning events. 

You can maintain an online resource library where your reps can find and contributes new information whenever they want. If you have a predictable slow season, you can have your teams join webinars to rejuvenate their knowledge base and motivation. 

Training New Remote Sales Reps Needs Your Flexibility

The thing about hiring and training, in general, is to know you’re dealing with people. What does this mean? 

For one, no two people are exactly alike. Besides being unpredictable at times, everyone absorbs information differently. The reasons why we succeed or fail can greatly vary.  You also need to be aware of when you can’t be flexible. We’ve talked about having a good foundation, positive attitudes, and continuous learning. When you realize that someone on your team is missing any of these, you need to take action immediately. Hopefully, the action fixes the issue, but there will be cases when it does not and you will have to accept that someone you hired isn’t right for your team.

Owners of startups, small businesses, and other new ventures, you have so much on your plate. You take care of sales, customer service, billing, and an endless list of duties. Among everything, developing and training new remote sales reps, or other people you hire, may take a backseat. 

If you take anything from this post, I hope it’s that investing in the people you hire is actually one of the most important things you can do. Get your team the right foundation, ensure they’re happy and knowledgeable. 

Then, and only then, will your business gain access to previously untapped growth potential.

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