Scaling Sales And Overcoming Problems

How To Scale Your Sales Without Crashing & Burning

When you're ready to scale your business, many obstacles may stand in your way. If you want to skip the learning curve and know what problems await you as you scale and grow your business, this first post will get you started.

NOTE: This is only going out to my private list and is part 1 of a 14 part series. I may release the final version either as a book or as an epic blog post. I would appreciate any feedback you can give as I release these posts over the coming weeks.

The focus of this post is on Scaling Sales. In the future we’ll look at:

  • Customer Service

  • Finance/Cash Flow

  • Culture/Vision

  • Human Resources

  • Compliance

  • Marketing

  • General Business

  • Product/Service

  • Fulfillment

  • Brand/Positioning

  • Reporting/Tracking

  • Technology/Systems

  • Management/Executive Team

I've scaled multiple companies from zero revenue to seven figures, with my largest reaching over $20MM/year and landing me on Inc 2500. The year before if not for a technicality I think we would have been an Inc 25!

In this article, you'll discover all the pitfalls I faced so you can avoid the mistakes and hopefully have a smoother, quicker ride to massive growth.

Let's dive in, shall we?

How To Grow Sales In Your Business

Sales are the lifeblood of any business. If you're not making sales, then you're not making money. Often in newer companies or smaller companies, selling is an afterthought. This is usually because the owner or a star employee "handles" sales and is pretty good at it. However, as you scale your business, you will need to turn sales into a systematic process that produces a consistent result.

Let's now dig through the main problems of growing sales so you can start working on them immediately.

1) Not Hiring Sales People Soon Enough

This is a big one. When you want to grow sales, you're going to need more people. More people means more money, usually. And many owners who aren't in a "scaling mindset" tend to want to conserve cash instead of spending it. This is wise early on as you are going from a baby company to an adolescent, but at some point, we all have to grow up.

So, when you want to grow sales, you need to add more salespeople. And this is where it gets interesting. You need to add these salespeople BEFORE you desperately need them. I've made the mistake of waiting until I had to have salespeople to keep up with the lead flow. Guess what happens?

  • You end up hiring less qualified people because you're in a rush.

  • You don't properly train the people you do hire, setting them up for failure.

  • You spend a lot of money all at once hiring 5-6 salespeople in a single month when you could have hired 1-2 salespeople for the last 12 months and only kept the high performers.

  • You can let in bad apples who tend to ruin (or at least damage) the culture.

So, how do you overcome this business problem and solve it? Easy. You start planning ahead. You need to hire salespeople before you need them. Start with adding 1-2; do it right now. You can be very particular in your search. The best time to borrow money is when you don't' need it, and the best time to hire salespeople is when you don't need them.

This gives you time to get the right people on board and ensure that they are competently trained. You can then put the new salespeople through an excellent training program and get them mentored by one of your existing sales rockstars.

Even though this is an expense early on, this move can help you scale faster if done correctly. If you have the budget for it, continue adding 1-2 new reps each month, and don't be afraid to fire fast. Hire slow and Fire fast as the saying goes.

The other advantage here is that by adding new reps monthly, you aren't inundating your system with a bunch of onboarding problems. You're adding flavor to the culture instead of potentially ruining it by throwing in too many new employees at once.

2) Not Having A Sales Training Program

Scaling is all about stretching your existing systems to their max. You are pulling and pushing things until they break. And there's nothing wrong with that. You won't know you've crossed the line until you've crossed it.

And one of the most significant areas that you can improve upon in sales is to create a sales training program. It doesn't have to be elaborate, especially at first. What you want to do is get it started.

There are few things more daunting than staring at a blank screen to start writing a sales training manual. Let's break down what should be part of the manual and program. Then we'll look at how to get it started.

You should have (at a minimum) the following:

  • An overview of the product/service you are selling.

    • This should include all features and benefits.

    • This should include price points (including specials, payment plans, etc.)

  • A walkthrough video showing how to use your Sales CRM.

    • Go very slow and be thorough. You can use tools like Camtasia or Loom to record this.

    • Make sure to spare no detail. If your sales rep has to add a customer profile, show them how to do this. As we'll talk about later, in my experience, excellent salespeople aren't technical.

  • An FAQ that covers all the questions a potential customer may ask as they go through the buying journey.

  • A document explaining the buyer's journey.

    • This includes where they came from, what they want, and why your product solves their problem.

  • Marketing materials! This is a big one. Showing your sales reps the marketing materials that generate the leads is so important. It helps them understand the frame of thought the potential customer is in based on what they responded to.

    • As a bonus, salespeople can then give marketing lots of good feedback on the ads, the angles, and hooks that attract the right customers.

  • A Sales Mentor.

    • Assign each new rep a sales mentor who guides them for at least the first 60 days.

    • This mentor can get paid an override on commissions the new rep makes to compensate them for their time.

    • The mentor should meet at least weekly to review the progress of the new rep.

    • Another tip - Offer a big fat bonus to the mentor if they can get the new rep to last six months in the company (at your discretion, of course).

  • Call/Zoom/Audio Recordings of Sales Calls.

    • There's nothing like hearing a real sales call happen.

    • Share calls that worked and calls that didn't work.

    • Have the salesperson explain to you why they think the call went well or went poorly.

    • The more they can explain in their own words, the higher the likelihood they'll remember the lesson.

  • Culture & Vision documents.

    • Make sure you talk a ton about your company culture and who you are and where you're going. We'll have a full section on this during this article, but it's essential to include this with your salespeople.

    • Sales more than any other department (except customer service) can affect how your target market views your company.

  • Anything else you think salespeople need to know.

    • Because I don't know your business, I can't make an exhaustive list. There are most likely other aspects of your business that sales reps should know about.

    • Maybe you want to include your company history or some more in-depth technical specs. 

3) Using Tired Sales Tactics

The 1970s and 1980s produced lots of cool stuff like classic rock and disco. But it also created a sales philosophy that has mostly died out in the minds of everyone except sales managers and trainers.

Back then everything was all about the ABC's (Always Be Closing!) and scarcity and urgency and pressuring the prospect into making the purchase. The view was if it wasn't a yes, it was a no and a no meant they were never coming back.

See this favorite scene of mine from Glengarry Glenross:

While some of these tactics work on some people, they tend to backfire in general. That's because the way we sell has changed. One of the best books on improving your sales is a great read called SPIN Selling. (Affiliate Link)

Here's what SPIN stands for. You can read more from here (yeah, that's the domain haha).

"SPIN stands for the four kinds of questions successful salespeople ask their customers: Situation, Problem, Implication, and Need-payoff. It works from the theory that relationship selling is customer-centric. It requires you to adapt your selling process to your customer, and it delivers personal solutions."

Reads like common sense, right? However, many salespeople miss the boat on this. As someone who has overseen a sales team of 50 people, I can tell you that many get caught up in making the sale and miss the point - helping the customer solve a problem.

That's what makes SPIN such a good protocol. Find out where the customer is on the buying journey. This is their current situation. Then, dig deep on what problem they are trying to solve. Don't just focus on the surface problem, either. Get emotional. Even if you're selling to a no-frills engineer, there's an emotional component to his problem.

Next, talk through the Implication of that problem. This can be extrapolating out what will happen if they don't' solve the problem and how much that may cost them.

But here's the key. Don't tell them anything. Let them tell you. You do this by asking questions. "What do you think will happen, Bob, if you don't' update your printers soon?" Then let him talk.

If he gives you a good reason, ask him to prove it. "Interesting. Why do you think not having new printers would cause the business to lose money? And why are you thinking about doing this now instead of just waiting till the printers wear out completely?"

Notice how the questions prompt them to answer us with their reasons. Then, to justify those reasons to us. We are now in the role of a consultant instead of a salesperson. GOLD.

And finally, there's the Need-Payoff. This is part probing questions like we've been talking about and the idea that your product or service can solve customer needs as they've presented them. And that's a key. Let them tell you what's going on, what their problems are, what those problems mean, and finally, how your product can solve their needs.

Then, and only then, can you ask for the sale because the prospect is already sold.

I did a decent job recapping the SPIN process, but I highly suggest you check out the book linked above.

4) Allowing Sales People To Get Too Aggressive To Hit Numbers

This is another one that is easy to solve once you become aware of it. Too many growing companies let salespeople run rampant and say just about anything to close the sale. Remember what happened to Wells Fargo with their sales team?

There are two leading causes of aggressive salespeople: Impossible to hit targets or lax compliance. Thankfully, you, as the owner, can help prevent both of these issues as you scale.

You should meet with your Sales Officer at least weekly and go over the numbers. Look for trends up and down and make sure the targets are within reason. Also, meet with your Compliance Officer to ensure that all rules are followed.

I speak from personal experience here. Compliance, if not handled correctly, can bite you as a company. So, make sure you stay on top of it.

As a side note, you should know that as you scale and grow and add more volume, the law of numbers dictates that your conversion rates will decrease while your total sales will increase. Just keep that in mind as you set expectations for your sales team.

Also, if you're saying I don't have a Sales Officer. I don't have a Compliance Officer. Guess what? You do have them. Just look in the mirror. That job is yours until you can replace yourself.

Is it weird to hold meetings with yourself? Sure, but this is just an abstract way of thinking about the different hats you have to wear as the proud owner of a growing business.

But let's talk more about that Sales Officer now.

5) Not Hiring A Growth Sales Officer

Another big problem you'll face as you grow your business is that you'll need to hire a sales officer or sales manager ASAP, but if you haven't done it yet, you may not want to bite off on it.

That's because scaling often means you are investing upfront for a return later. That is why hiring a sales manager/officer as soon as you can is so vital.

You want to replace yourself in all areas as you scale so you can focus on the bigger picture. One of the most fun things about scaling is when you realize how deep each job role can go.

Let's look at just a small sampling of what a Sales Manager can do day-to-day:

  • Interview, hire, and onboard new sales reps

  • Write new scripts for the sales team to test out

  • Listen in on sales calls

  • Do weekly one on ones with each salesperson offering coaching and feedback

  • Create reports to track different sales metrics

  • Hold daily stand-up meetings (rah-rah calls)

  • Come up with weekly, monthly, and yearly contests

  • Create bonus structures to further incentivize your sales team

  • And so much more

I see many business owners afraid to hire a sales manager or sales officer because they don't think they can afford one. If you're ready to grow your business, you desperately need someone focused on increasing sales.

As I was saying earlier, it's truly amazing how deep a job can go once you give it to someone else. A great sales manager focused on growth can be a game-changer.

What kind of person should you look for? In my experience, you want someone who has done the job before (background), has worked in the same or very similar industry, understands compliance and has dealt with it before, and finally someone that is a great culture fit.

If the idea of talking to the person 2-3 hours a day seems like it would be hard on you, then don't hire them. Because early on, you will meet all the time to plan and strategize. You also want to make sure they understand how to reiterate your values and culture to the sales team.

6) Not Properly Incentivizing Salespeople

Now, I'll let you know that I'm a little biased against salespeople. They are good and they are needed. But many I've met have oversized egos (which makes them great salespeople ironically). They are straightforward and have no qualms asking for money. This means they'll have no fear asking you for higher commissions when they start bringing in the sales.

So with my bias out of the way, let me explain a significant issue I've seen with business owners who want to scale a sales organization. In a sales-focused company, like it or not, sales are the lifeblood. Yes, lead flow is equally important, but the marketing department isn't on the phone all day. This is another reason why I think salespeople want to get paid more than others. In many ways, it's a manual job.

So the issue I see is that business owners can come to resent salespeople because of what they earn. They end up trying to take away commissions because they feel like the reps have "gamed" the system. While you do need to watch out for that, you don't want to go too far.

As you scale, you'll need more and more salespeople. To bring them in, you'll need to offer aggressive compensation and other goodies to keep them happy— health insurance, car bonuses, annual vacations, etc.

Because happy salespeople make happy business owners. And don't feel bad if they make more than you. That's ok; you're building a sellable asset, they have a job. I remember in a previous company, our top sales rep made almost 5X what I made. And I was the CEO!

But that's ok. Check your ego and take care of your salespeople. Incentivize them for making sales and make it as generous as you can, always remembering to leave room for them to grow into higher commissions based on production.

Do this, and you'll see some great results.

7) Expecting Too Much From Sales People

While we're on the topic of salespeople, let's talk about your expectations. I've seen in multiple companies now where too much is expected from salespeople. In my experience, salespeople are generally not very technical by nature. They are more talkative and friendly. Asking them to use a complicated CRM system may be a bit much for them.

How I got around this was hiring an assistant for my best salespeople. I turned it into a sort of bonus for them. And they LOVED it. Instead of having to log all the details of the call, they could keep "scratch notes" and then have their assistant go into the CRM and update all the details.

You do want to be careful here, however. If you have an elaborate sales CRM, you want to make sure it's being used, especially for automated followup. That is why you will need to spend extra time with the sales team making sure they know how to use it.

Also, make sure you continually check to see that they are using the tools provided. Salespeople can tend to be very independent and want to do things their way instead of following a system.

Make sure you help them as much as you can, remember they aren't usually very technical, and keep up with them to ensure they are using your systems. And if they're making the company money - get them an assistant so they can spend their time talking to leads!

8) Not Expressing Concerns To Marketing

This is one you shouldn't have to worry about too much because salespeople usually do a great job complaining about lead quality. However, as you scale your business, you want to make sure you open the door to allow your sales team to communicate directly with Marketing.

Now, there are a few caveats here. First, don't just allow any salesperson to speak directly to marketing because they will, and it will quickly turn into a fiasco with ten different salespeople saying ten different things.

Some will say how great the leads are, while others will complain that these are the worst leads they've ever seen. You have to create a filtering process. This is where you have a few options.

The quick fix is to make sure you are using lead scoring in your CRM. Automate it as much as possible, but also have the sales team update the scoring of their leads frequently. These reports can go to the Marketing team, who can make adjustments to the ads and channels based on this feedback. This is quantitative feedback and marketing loves it.

Another option is a weekly "Lead Quality" meeting held by your Sales Manager. Let each rep talk and share their experience with leads that week. This is very useful in general because if a sales rep who thinks the leads are bad hears another rep saying how great they are and how they made five sales, the underperforming rep will now be on notice.

Then, your sales manager can create qualitative feedback reports recapping the "lead story" as presented by the sales team. This information will provide color to the marketing team once the sales manager presents it.

9) Expecting Too Much From Marketing

This is the other side of the coin I've seen from sales teams and even the sales manager. Marketing has a lot of work to do. They have to create avatars, decide on lead channels, write ads, set up testing, and tracking, etc.

Many sales managers and salespeople expect to speak only to the most qualified, money in their pocket, "ready to buy now" customers. This just isn't possible.

It's almost like Sales is asking Marketing to go out and find me the customers who want to buy today and only send me those. See how crazy that sounds?

There's this thing called the "Buyers Journey", and it's challenging to know exactly where someone is on that journey. Depending on your market and the product and price point, the best marketing can do is find someone on the road to your product.

I know with long-tail keywords you can get highly targeted leads, but these leads are few and far between, and when you're scaling, you are looking for quantity as well. Remember, you've got to keep your salespeople fed leads, or they go hungry and leave.

How do we solve this issue of salespeople who want too much from marketing? It's pretty easy. Just put them on a high-quality lead diet. Meaning, give them only 1-2 leads a day that you think are the best. Quickly, they'll see they need more leads if they want to make any real money, which has solved the problem for me in past companies.

9) Allowing Sales To Completely Drive The Show

This one is more a word of warning than anything else. You must keep things in balance. Don't let sales run the company. You need to stay focused on your core values, who you are, what you believe in, and why you exist.

Sales organizations can get into trouble when they create a "sales at any cost" mentality. Sometimes, the best feeling in the world is telling a customer No. In fact; if you can afford it, I would offer a commission to sales reps that weed out potential problem customers and tell them they're not a fit for the product or service.

In the long run, you'll save money by not dealing with refunds, customer service issues, and negative reviews from such customers.

10) Overpromising & Angering Customer Service

Oh, the simple life of a salesperson. Can your product do X? Yep! Do you guarantee I'll have my system set up and implemented in less than 60 days? For sure!

Typically salespeople over-promise. And that's a horrible thing as you scale. Early on, you can make up for it by offering freebies, crashing the project with extra resources, etc. But when you're scaling up, you don't have additional resources to spare.

So, scaling is the time when you need to get clear on your product delivery. What do they get? How? When? How fast? What about bonuses? What about customer service? Who do they call? When can they call?

The list is long, but it's essential.

You want to ensure that sales and support/fulfillment are on the same page. Otherwise, you are in trouble. And trust me, the customer support people have been in a 50-year war with salespeople.

Salespeople feel like they make all the money for the company while customer support people feel like they are cleaning up a mess created by sales.

Your job as the owner is to make sure that you maintain control of what salespeople say. This is vital for compliance either way. Then, make sure that you are getting essential feedback from the customer support team weekly.

Sales may be King, but Customer Satisfaction is God!