12 Things to Consider When Hiring Remote Sales

You’ve decided it’s time to hire a salesperson or team to expand your business. If you’ve never dealt with salespeople you may need to take a step back and review the questions below BEFORE trying to hire.

Typically, the decision to decide to add a remote sales team or salesperson is rooted in a company needing more business than they can currently produce. So what you are asking of this new hire is, “I want you to come into my business, which you know nothing about and produce better results than I can, faster than I ever have, and compensate you way less than I compensate myself.” Agreed?

I come across business owners weekly that think all they have to do is hire a salesperson, show them their product, and then the salesperson will do everything else. This is most prevalent in companies looking to hire for straight commission sales because they mistakenly assume that there is no risk in it for them.


Often business owners’ expectation of a sales team is perplexing to the salesperson because on one hand, they expect miracles from their sales team, but on the other hand they give them very little to no respect or support. 

Good salespeople are a special breed and their personalities take special care and treatment. Your sales team are ambassadors of your brand to the marketplace. They can make or break your company. You should treat them with a very high level of respect and appreciation as they are the ones that are going to add the most to your bottom line and all the good ones know that.

If you’re not providing the proper environment you are not going to attract or be able to keep good salespeople. You will only attract and end up with the desperate and unskilled.

These questions will give you some things to think about before you put that ad together for someone to produce miracles for you in the marketplace.

  1. What experience do you have managing salespeople or a sales team?

This is a big one and there isn’t a simple remedy if you don’t have experience dealing with salespeople. If you don’t, you might want to consider hiring a sales manager, at least temporarily, to help you attract and train the right people. Salespeople have their own language and processes and not knowing how to deal with that will cause a lot of heartache and failure.

2. Thinking of hiring for straight commission? Have you ever been able to support yourself for over 6 months on a straight commission sales job?

I ask this question a lot to people hiring for straight commission. If you haven’t done it yourself, it’s probably because you don’t want to because it’s too intimidating or scary. Remember that.

3. What current systems do you have in place for your sales team? Have you mapped out the lifecycle/timeline of a lead to client to launch/exit?

Expectations and processes should be clearly defined and communicated to your sales team. Salespeople have tons of soft skills but they still need a clear map and clearly defined processes. Your company should be able to visualize what “sales” look like. If you’re looking at straight commission sales, you need to be doubly prepared for this.  You’re hiring them to do sales not create SOP’s. Real sales pros will not tolerate you not having your stuff together. 

4. What sales materials and marketing have you prepared?

Sales and marketing are 2 different things requiring different skill sets. Marketing is what you do to get people in front of your salespeople. That could be ads, sign-ups from your website or trade shows, people you’ve done business with in the past, whatever. It will be hard to hire anyone of quality if you don’t have these assets in place. Think of a waiter in a restaurant. Your sales team is the wait staff. Everything else that gets those butts in the seats is marketing.

5. What expenses are you covering for the sales process?

More on this below, but you just need to understand that remote salespeople do have expenses related to selling for your business and I would think you would want more control over your client data and the process so you should be providing them with all the tools they’ll need to be successful with your company.  Again. Keep reading.

6. What training are you providing and did you plan on compensating for that time?

I think Brian Tracy said, “Would you rather train them well and have them leave or not train them well and have them stay?” That pretty much says it. Salespeople need stories to tell about your company and your services so they can project a confidence in your offering so make sure they have that. Take the time and pay them for their training time.

7. Are you providing a phone number, email, landing page, bio on your site?

If you’re not providing this stuff to a remote salesperson your leads/clients you’re making your business look unprofessional and creating a shaky foundation for successful sales. You need to have consistency and control over your client data and all communication. If you are using a contract salesperson you’ll want to have the power to turn off access to your systems and client data to be able to assign them to another sales team member if things don’t work out with your contractor. Lots of free or low-cost options for this.

8. Do you have a CRM to manage the leads and contacts? If so, what is it? If not, how do you want contacts managed?

Along with the list in #7, having a good CRM that the salespeople work out of keeps all the communications with prospects and clients in one place and most also provide for reporting so you can see what your team is doing without having to call or have them stop their sales activities to provide you with a report. There are plenty of good free options if you’re just getting started.

9. Do you have a dialer and/or phone system that the salesperson will be using or would you want the salesperson to provide that?

Dialers are great. They allow the sales team to grind through a high number of calls quickly and efficiently and most allow for calls to be recorded so you can check in when you like. Some even allow for pre-recorded voicemails to be left if people aren’t available which helps with a consistent message. Costs on these have come down greatly in recent years, usually $.05 -$.10 per minute. At the very least, you want to provide a phone number for the salesperson to call from. You could get a Skype number for less than $3 a month.

10. How are contracts, agreements, and payments going to be handled?

You definitely want control over this utilizing a system where the salesperson only needs to input a few details and be able to present your agreements and contracts quickly because that’s when the $$$’s roll in. You should also make sure that your client’s financial data is handled in a secure and proper matter. If it’s not, you are opening yourself up to serious financial repercussions if your clients’ financial data is somehow compromised.  Don’t be stupid with this or it could literally steal your personal and business’ future.

11. How many concurrent clients can you handle at once? What’s your capacity?

This is an operational question and it’s the one that stumps most. If you can only handle 5 clients at a time and you are requiring that your sales team bring in 10 deals a month you’re stepping into a nightmare if your sales team starts hitting their numbers. Might sound silly to you, but it can cause a real problem for you if you don’t consider capacity.

12. If a salesperson exceeds your capacity how do you plan on compensating them if you cannot deliver?

So you’ve hired out your sales and they are successful, wildly successful and now you need them to STOP so you can catch up. What do you do without losing your golden goose and keeping the reputation of your company?

BONUS!!! 13. How are you going to keep your sales team happy and motivated so the good ones stay?

Sales pros with good skills can generally find work anywhere and since they are constantly networking and impressing people. Think about the last salesperson that you spoke with or met that you were impressed with. Did you think to yourself, “Man, I wish they worked for me.” Guess what? Every decision maker your salespeople talk to are thinking the same thing.

For talented sales pros, you should understand that it’s not just about money.  It’s more about ease, comfort, respect, acknowledgment, and knowing they are appreciated.

Hopefully, you have a better idea of what needs to be considered when bringing on a remote sales team or salesperson to your company. The more you are prepared, the better talent you will attract.

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