It’s not uncommon for the founding owner of a small business to be the company’s rainmaker. That comes at a cost when the business is growing because it doesn’t allow it to scale sales growth.
One person working hard is not a business — it’s a glorified job. And it’s a value-killer if the company doesn’t fix that by the time the owner is looking to retire.
Investors and acquirers tend to place a lower valuation on businesses where the owner personally carries the lion’s share of sales responsibility. Why? Because such companies are more fragile. If the owner walks away or is unavailable, the pipeline may dry up, and the business could falter. (The same is true if the owners are the only ones who deliver a highly skilled service, like dentists, accountants, physicians, and lawyers, but that requires different solutions than we’ll discuss today.)
According to research from the Value Builder System, which studied more than 70,000 businesses, companies capable of surviving a three-month absence of the owner have more than twice the likelihood of receiving a premium acquisition offer — defined as greater than six times pretax profit. The less your company depends on the owner to sell, the more valuable it becomes. Getting to that point, however, is no small task.
Junior employees rarely match the owners’ sales results, especially when the owner has the expertise, authority, and companywide decision-making power. Customers are comforted that if something goes wrong, they can pick up the phone and speak directly with “the boss.” When that same pitch comes from a less-seasoned salesperson, it can feel hollow, lacking the built-in credibility that comes with having your name on the door; this is true even if the person is experienced and capable.
3 Strategies to boost your team’s sales game
The good news is that there are concrete steps you can take to level up your entire team’s sales game and, in turn, ensure your company thrives with or without you.
1. Give Your Team a Differentiated Value Proposition
The Challenger Sale concept
Matt Dixon, co-author of The Challenger Sale, suggests arming your employees with an answer to one fundamental question: Why should your prospects buy from you? The key is that this answer should have nothing to do with “superior customer service.”
Your customers can get one-hour delivery from Walmart, choose from thousands of shows on Netflix, schedule cash to move from their bank account to their brokerage account and have it automatically invested, and have someone tow their broken-down car at 4 a.m., all by pushing a button on an app. Nobody cares about your customer service; it’s a de minimis, not a differentiator.
Instead, Dixon’s framework emphasizes “commercial insight,” which challenges customers’ assumptions and offers perspectives they might not have considered. When your salespeople can provide unique insights — rooted in your company’s innovations, research, or approach — they create a conversation about outcomes rather than process.
Elements of a great selling proposition
A compelling sales pitch must speak to something customers genuinely care about and differentiate you from the competition. That uniqueness can become the fulcrum of your pitch — if it is something your prospects value and if you can prove it.
Consider the experience of Mira, who founded an architecture agency in Wellesley. While Mira had built a reputation for impeccable design work and fast turnarounds, her junior sales reps struggled to evoke the same confidence when pitching to new clients. Realizing “customer service” was too vague, Mira tapped into what set her agency apart: getting everyone on the same page by having customers view specifications visually through a real time, virtual-reality editing tool. This system allowed her team to collaborate instantly with clients while making it fun for them.
Equipped with a short demo, the junior salespeople started focusing their pitch on the agency’s real-time collaborative creative process, emphasizing how it helped the client move from vision to reality and reduced miscommunication. The process was easy to demonstrate and aligned with clients’ top priorities: speed and accuracy.
When prospective clients saw the system in action, it became clear how the agency was different and why it was believable. The pitch resonated by quantifying “speed” (a 50 percent reduction in time-to-completion of blueprints) and demonstrating how fewer errors translated into cost savings. This tangible proof helped transform the entire sales team into confident evangelists of the agency’s secret sauce.
2. Systematize Your Sales Training — With a Digital-First Edge
The power of a playbook
The founder knows every nuance of the company’s product, every competitor’s weakness, and every question a prospect might ask. However, less tenured salespeople can’t replicate that know-how and natural approach. They need a structured roadmap — especially one that reflects the realities of how buyers make decisions in the digital age.
Instituting a sales playbook is essential. This document (or digital resource) should outline your company’s unique selling proposition, competitive positioning, and customer personas. Include scripts, FAQs and sample presentations — everything a salesperson needs to handle common scenarios. When new hires join, they don’t just learn by “riding along” or passively shadowing; they have a curated resource detailing your proven processes.
Deploying an AI-driven sales simulator
A midsized software company in Boston historically relied on its founder, Tom, to close big deals. As the company grew, Tom realized that his team needed a scalable training solution. Tom had members of his sales team download Meta’s Llama app (a large language model with voice and conversation enabling) and practice their script.
If you’ve ever had your team roleplay sales scenarios, you know how much everyone hates it. It’s awkward and feels stiff. Llama allowed people to practice on their own, using natural language. This elevated the script to a conversation and prepared the team to discuss, not dictate.
By practicing in this virtual environment, the sales team honed their responses and built confidence, all while receiving instant feedback. The system would highlight key phrases or missed opportunities for advanced questioning techniques.
The team would then copy and paste the transcript, share it for everyone to read, and meet to discuss their best ideas and “aha” moments. When Tom began to focus on strategic partnerships, the rest of the team was equipped to keep the sales funnel moving.
3. Empower Your Employees with Accountability — And Recognize Their Wins
Incentives aren’t just about money
Once you’ve given your employees a compelling pitch (Step No. 1) and the training to master it (Step No. 2), the final key is consistent accountability paired with recognition. While financial incentives tied to the outcome certainly matter, they don’t always give employees a deep sense of ownership.
People often crave autonomy, mastery and purpose in their roles. You’ll nurture a more motivated, high-performing team by aligning your sales goals with your team’s personal and professional development.
Structure and transparency
Set clear, measurable targets for your sales force. Define territories, industries, or product lines for which each rep is responsible, and use transparent dashboards to keep track of progress. When reps can see their numbers in real time — relative to peers or monthly goals — they stay engaged.
Regular check-ins or pipeline reviews help identify bottlenecks and give you a chance to coach, rather than waiting until the end of the quarter and hoping for the best. Shout-outs are also learning opportunities. Reps should be encouraged to share their winning strategies, and everyone on the team should learn from one another’s triumphs.
Focusing on these three core strategies gives your employees the tools and motivation to sell effectively, making your business more substantial and attractive to potential acquirers. Not only will you see an uptick in sales performance, but you’ll also free yourself to focus on strategic opportunities.
This article first appeared in the Berkshire Eagle on January 31, 2025.
