Avoiding the superstar sales rep trap

A man is sitting at a table with a laptop and shaking hands with a man.

For your business to be valuable – and sellable one day – you need some way to generate sales after you’re gone. Many business owners hire a superstar salesperson to replace themselves as a rainmaker but that’s a trap.


 By replacing yourself with a single salesperson, you’re simply trading a dependency on you to dependence on a sales rep, and your business will be no more sellable as a result. When we analyzed the users of The Value Builder Score, a self-assessment test business owners use to understand how to drive up the value of their company, we found that businesses who could easily replace their top salesperson are more than twice as likely to get an offer to buy their business than those companies who are overly reliant on a single salesperson.


To be as valuable as possible, your company needs a sales team – not just a single salesperson. But how do you build an entire sales team? Wouldn’t it be more prudent to hire a sales rep first? The answer is no. Hiring a single sales rep will only keep your business reliant on one person. You need a team and the faster the better. Here are three tips for building a sales team on a shoestring:


 1. Charge up front


Sales reps are expensive to find and train, so in order to avoid running out of cash before they are fully ramped up, consider switching your customer billing cycle to charging some or all of your bill up front. If you stagger your billing, you can simply ask for a larger portion of your payment up front. If half your customers agree to the larger deposit, you’ll have more cash to build your sales team and more time for them to train up.


 You might also consider switching to a subscription or service contract model as most people are used to paying for subscriptions up front. Try for an annual contract with an incentive for full payment in advance. For example, if you charged $1,000 per month for a maintenance contract but offered clients a $10,000/year option provided they paid up front, you would have ten thousand dollars in the bank for each contract sold. If a fully ramped up sales rep is able to sell ten service contracts a month, would it be reasonable to assume a new rep could sell three per month? If so, a new rep should be able to quickly get to the point where they are covering their monthly cost to you.


2. Carve territory into small chunks


Sales territory is an asset of your company and, like giving candy to a baby, it is easy to offer and hard to take back. Carve up your market into sales territories that provide enough opportunity for each rep to make money. It’s okay to leave a territory unfilled for years, so avoid the temptation to give the territory to another rep, as it will become impossible to take back when you’re ready to fill the position.


3. Hire a second rep as quickly as possible


If at all possible, start by hiring two sales people, not just one. Sales people thrive on competition, and in order to be a sellable company, you need to be able to demonstrate to a buyer that your sales are driven by a sales team and not just a high performing salesperson. If you’re charging up front or on a subscription model, you should be able to quickly get to the point where each sales rep is at least covering their costs to you.


Replacing yourself as your company’s rainmaker is the right strategy, but avoid trading a dependency on you to dependence on a superstar sales rep. Instead, hire a sales team and watch your company – and its value – grow exponentially.

Get Free Business Valuation

or

Schedule Free Consultation

Recent articles for you

A Strong Business but a Modest Multiple

By Kim Santos • June 16, 2025
When Sean McAuliffe sold his company, he had a lot going for him. His distribution business was generating nearly $19 million in revenue. Margins were healthy. Growth was solid. And yet, when it came time to sell, his company was valued at around four times EBITDA, a relatively modest value for a $19 million company. The reason? Sean didn’t fully control his supply chain—and buyers noticed. Dependency Makes Buyers Nervous Sean’s model was simple. He bought car key fobs from suppliers in Asia and sold them to locksmiths across the U.S. It was a classic distribution play: source cheap, sell smart, and manage relationships. Sean executed well. He even created his own brand, Keyless to Go, and FCC-registered his products—moves that set him apart from competitors. But despite these efforts, Sean was still reliant on third-party suppliers. He didn’t own the factories. He didn’t control manufacturing. His business was exposed to the decisions of vendors half a world away. In today’s environment—where tariffs and geopolitical tensions can change the cost and availability of overseas goods almost overnight—relying on foreign suppliers feels riskier to acquirers than ever. This kind of dependency is exactly what The Value Builder System™ measures through the Switzerland Structure—one of the eight key drivers of company value. The Switzerland Structure assesses whether your business is overly dependent on any one customer, employee, or supplier. Buyers pay a premium for companies that aren’t beholden to any single relationship. Why Monopoly Control Drives Value Contrast that with businesses that own their brand, control their production, or have proprietary products. Companies with a defendable moat—what we call Monopoly Control—are 40% more likely to have received a written offer to acquire their business, according to analysis of more than 80,000 business owners who have completed their Value Builder Score report. When you control your product and customer experience, you influence your valuation upward—giving buyers fewer reasons to discount your business. The Takeaway for Owners Sean still built a great business. His execution created life-changing wealth. But if he had owned the supply chain or had exclusive manufacturing rights, he likely would have commanded a higher multiple.  The takeaway for business owners: Building a valuable company isn’t just about revenue and profit. It’s about creating a business that can thrive without being dependent on any one customer, employee, or supplier.

How to Double Your Chances of a Premium Acquisition Offer

By Kim Santos • April 21, 2025
Value Builder Analytics, drawing on proprietary data from over 80,000 business owners, found that companies that can run without the owner for at least three months are twice as likely to receive an acquisition offer above 6x EBITDA. The concept is simple. The execution? Not so much. Take Kristie Shifflette for example. She was an early master franchisee with Orangetheory Fitness, a one-hour, coach-led workout that uses heart rate zones to boost calorie burn during and after exercise. When she opened her first location, she did it all—marketing, hiring, payroll, and even handling construction headaches. It worked but only because she was working constantly. As she expanded, things started to break. With two locations, she was stretched. At three, it became clear: The model only worked when Kristie was the model. She knew she needed to change. Kristie stopped focusing on being in the business and started focusing on building the business. From Operator to Owner Kristie started documenting everything. From pre-sale processes to day-to-day studio operations, Kristie developed detailed playbooks that codified exactly how her Orangetheory locations should run—without her. She created a compensation structure for studio managers that gave them ownership over their results: modest base salaries paired with meaningful bonuses tied to net member growth and total revenue. Top-performing managers could double their pay, and they were treated like mini-CEOs with full responsibility for their studio’s performance. By the time she sold her business, Kristie had built a company with 13 locations generating well north of $10 million in annual revenue. Some of her top-performing studios, like the Chapel Hill location, were bringing in revenue of $2 million a year, with EBITDA margins around 40%.  Kristie’s story includes an important lesson: Make yourself less essential, and your business becomes more valuable. If you’re still the one opening the door in the morning and locking up at night—literally or metaphorically—it’s worth asking: What would break if I stepped away for 90 days? Start there. Whether it’s building a playbook, empowering your team, or simply learning to let go, taking even one step toward reducing your involvement makes your company not just more valuable but more enjoyable to own.

Why Imperfections in Your Business Don’t Make It Unsellable

By Kim Santos • April 14, 2025
For business owners considering their endgame, learning what makes a company valuable can feel overwhelming. Buyers prioritize factors like recurring revenue, a differentiated product or service, and a leadership team that operates independently from the owner. If a business doesn’t check every box, it can seem as though selling is perpetually just out of reach. But perfection is not a prerequisite for a sale. While improving the key drivers of value is important, an imperfect business can still be highly desirable to the right buyer. In fact, some acquirers actively look for businesses with fixable flaws because they see an opportunity to increase value. Blake Hutchison on Why Imperfections Can Be to an Acquirer’s Advantage Blake Hutchison, CEO of Flippa, has witnessed thousands of business acquisitions. Flippa is an online marketplace where business owners can buy and sell companies, particularly small to mid-sized digital businesses. The platform connects sellers with buyers looking for opportunities to grow or optimize an acquisition. In a recent Built to Sell Radio interview, Hutchison explained that many business owners assume their company won’t attract buyers because it has shortcomings. In reality, most acquirers aren’t looking for perfection—they’re looking for potential. Many buyers have a strategic advantage, whether it’s a strong distribution network, operational expertise, or access to capital, that allows them to take an imperfect business and make it more valuable. A prime example of this is the acquisition of PetCoach. How PetCoach Turned an Imperfection into a Selling Point PetCoach, co-founded by Brock Weatherup, was a two-sided marketplace designed to connect pet owners with veterinarians. The challenge for any marketplace business is keeping both sides in balance—generating enough demand from pet owners while ensuring there are enough veterinarians to meet that demand. PetCoach had built a strong product, but it lacked a broad distribution channel to acquire pet owners at scale. Without a solution, growth would remain limited. Instead of seeing this as a dealbreaker, Weatherup positioned it as an opportunity for the right buyer. That buyer was Petco. With more than 1,500 locations across the U.S., Mexico, and Puerto Rico, Petco had access to millions of pet owners. By acquiring PetCoach, Petco could instantly expand its offerings while solving PetCoach’s biggest challenge. Weatherup didn’t need to fix the scalability issue before selling. He needed to find an acquirer for whom the business’s weakness was actually a competitive advantage. Your Business Has Value—Even if It’s Not Perfect This doesn’t mean business owners should ignore the fundamentals of value creation. Strengthening factors like recurring revenue, customer retention, and operational efficiency will always increase a company’s attractiveness. However, not every issue needs to be resolved before an exit.  Instead of viewing imperfections as obstacles, business owners should consider how an acquirer might perceive them: A company struggling with customer acquisition may be a great fit for a buyer with an established customer base. A business with inefficient operations might attract an acquirer with expertise in streamlining processes. A company overly dependent on its owner could be appealing to a buyer with a strong leadership team ready to step in. As Blake Hutchison explains, acquirers are often looking for businesses where they can add value. The key is to position the company in a way that highlights its strengths while framing its imperfections as untapped potential. The right acquirer won’t see weaknesses as dealbreakers—they’ll see them as opportunities.