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fractional sales leadership

What An MBA Didn’t Teach You About Sales

The sales profession is challenging. You need to work hard at it to succeed. You need to learn from the best. You need to improve your skills continuously. If you think you can sell since you are a hit at parties and have a lot of friends, you may soon find that you are a failure as a salesperson. Blunt truth:

because the sales profession is so hard, you have to focus on doing everything in sales very well, or you will be considered a failure.

I call this blog, Skinned Knees because I try to relate all of the learning that I have done over the past 4+ decades (while skinning my knees in the learning process).

I hope that you learn from my mistakes so that your business will grow!

Hiring Your First Sales Leader? Build a Sales Machine, Not a Band-Aid

You are ready to hire your first sales leader when you are prepared to buy leverage, not relief. Titles do not grow revenue. A high-impact sales leader creates durable selling capability, reduces owner dependency, and raises standards through coaching, recruiting, and operating cadence. If what you really want is a second version of you to carry the number and keep deals moving, you are hiring a band-aid, and you will pay for it twice.

Most owners make this hire at precisely the wrong moment. The pressure is real, the pipeline feels fragile, and the business is starting to outgrow informal management. So the owner reaches for the obvious move: “We need a sales manager.” The problem is that the role is designed around short-term comfort rather than long-term capacity. The result is a well-paid administrative firefighter who inherits the chaos instead of fixing the system that creates it.

Before you post a job, clarify the objective. Do you want a revenue driver or a capability builder?

A revenue driver is a manager who helps you hit the number by conducting deal inspections, applying forecast pressure, and holding reps accountable. That can be valuable, but it is often a disguised need for personal production. A capability builder is a leader who creates repeatable performance by improving the quality of selling, tightening hiring standards, and building a coaching system that makes average reps better and good reps consistent. That is the role that changes enterprise value.

Here is the hard truth most owners avoid. If you design a role that combines selling and leading, selling will win. Always. When a leader has a quota, the business trains them to prioritize their own deals over the team’s development. They will “help” reps when a deal is in a late-stage, visible phase, then postpone coaching, recruiting, and onboarding because those activities do not pay this month. Over time, the team remains dependent, the pipeline remains uneven, and the owner remains in the middle.

Assessing readiness: leader or band aid

Readiness is not a revenue threshold. It is an operating decision. The question is whether you will let a sales leader lead.

The owner’s trap is hiring a leader while keeping day-to-day control: still running reviews, intervening in pricing, rewriting emails, jumping on calls, and closing important deals. In that environment, the new leader cannot build authority; they become an assistant with a title. You’ll be frustrated they’re “not taking enough off my plate,” while they’re frustrated at not being able to make decisions without you.

If you want a clean test, look for these warning signs:

  • You are still the primary deal closer and default problem solver.
  • You do not believe the company can make the number without your direct involvement.
  • You step into deals because you do not trust the process, the rep, or the forecast.
  • Your coaching is ad hoc, usually when something goes wrong.
  • Recruiting is episodic, triggered by pain, rather than continuous.
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Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

Autumn is the time of year for sales leaders, managers, and CEOs to begin laying the groundwork for next year’s success. Have you considered how your current sales compensation plans impact your team’s motivation and productivity? Now is the ideal moment to evaluate, adjust, and deliver these plans, preferably by December 1st. Doing so can significantly influence your team’s drive to close deals in December and build momentum heading into the next fiscal year.

Sales compensation should be motivating and rewarding for employees. It directly shapes your sales team’s behaviors and priorities. An effective plan incentivizes the right actions and deters the wrong ones.

Consider a common pitfall: salespeople holding back deals to inflate their numbers for the following year. Does your current compensation structure inadvertently reward this practice? If so, you’re unintentionally harming your year-end results.

To counter this, strategically incorporate compensation escalators and cliffs into your plan. Escalators progressively reward increased sales performance throughout the year. Higher performance equals higher commission rates, driving your sales team to push forward continually. 

Commission cliffs reset commission rates at the beginning of each year, creating a sense of urgency to close deals before the end of December. Communicating these compensation details clearly by early December ensures your team understands what’s at stake.

Don’t hold your team back!

Another critical compensation consideration is eliminating commission caps. While some organizations cap commissions to control expenses, this practice can backfire dramatically. Caps tell your top-performing salespeople that their exceptional efforts are neither valued nor rewarded appropriately. This demotivates your top talent and encourages them to seek opportunities elsewhere that offer uncapped rewards. 

Removing commission caps signals that the organization fully supports and rewards outstanding performance. Have you considered how much growth your company might achieve if artificial constraints didn’t limit your sales team?

When evaluating compensation, look beyond simple cost containment. Consider the true profitability of incentivizing increased sales volume. Once salespeople reach their targets and enter accelerators, each additional dollar earned typically comes at a lower incremental cost to your organization. 

Sales transactions earlier in the year have already covered the salesperson’s base salary once they have met their annual quota. In fact, at 100% of quota, the salesperson should have covered all their costs and their share of the overall company’s revenue needs. Thus, every extra sale at escalated commission rates still contributes positively to your overall profitability. 

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Elevating Your Sales Operations with New Sales Expert

My mission is to bridge the expertise gap that hinders many companies from scaling their operations to the desired heights. The core issue often resides within the sales sector of these organizations, and this is where my expertise becomes a game changer. Understanding the Challenge Many company owners, be they founders or inheritors of the business, come to a crucial realization at some juncture in their entrepreneurial journey. Despite their prowess in product development, manufacturing,… Elevating Your Sales Operations with New Sales Expert

August Newsletter

I hope you enjoy my August Newsletter Posts Subscribe I hope you enjoy my August Newsletter Published: Tue, 08/15/23 I hope that you enjoy my latest newsletter View the online version of this email. Football is starting at your local school and in the NFL. That used to mean that we were in Autumn, but now it means that we are simply in the dog days of summer. I hope the summer has been great… August Newsletter

The McDonald’s Lesson: Why a Diverse Sales Team Matters for Small Businesses

In the annals of American business history, few stories are as captivating as the rise of McDonald’s, immortalized in the 2016 biographical drama film “The Founder.” The story of Ray Kroc, a struggling milkshake machine salesman who transformed a local drive-in into a global fast-food empire, is a classic tale of ambition, innovation, and, controversially, ruthless business acumen. However, behind the gripping narrative lies a valuable lesson for small businesses today. The McDonald brothers, Richard… The McDonald’s Lesson: Why a Diverse Sales Team Matters for Small Businesses

The Kaivac Impact: Harnessing Faith, Innovation, and Sales Excellence in the Cleaning Industry

Revenue and profitability have grown since Sean helped Kaivac develop a higher level of sales professionalism. Recent results have shown a dramatic increase in revenue and profitability. The sales and revenue growth have allowed the entire family of Kaivac to prosper. The Robinsons have always considered their employees an extension of their family. The company’s prosperity is passed along to team members through a bonus structure for the whole company. It all fits into the spirit of Kaivac. Bob Jr. says, “Our organization was built to have heart.”

Two Tall Guys Talking Sales Podcast – Adapting Sales Strategies in a Changing World – Episode 32

In this episode of the podcast, Kevin and Sean discuss the necessity for sales leaders to adapt their advice and strategies in today’s ever-changing environment. With the numerous changes and challenges that businesses face daily, sales leaders must constantly evolve and stay ahead of the curve to help their teams succeed. The discussion touches on how being a trusted advisor to clients is crucial for success regardless of market shifts and economic turmoil. The ability… Two Tall Guys Talking Sales Podcast – Adapting Sales Strategies in a Changing World – Episode 32

Two Tall Guys Talking Sales Podcast – The Power of Service: How Giving Back Can Drive Sales Success featuring Jim Hardwick, Chief Community Officer of Sales Xceleration – Episode 31

In this inspiring episode of “Two Tall Guys Talking Sales,” the hosts, Sean and Kevin, welcome Jim Hardwick, Chief Community Officer for Sales Xceleration and Fractional VP of Sales. As a seasoned sales professional with 36 years of experience in healthcare, Jim shares his journey from climbing the corporate ladder to finding purpose and joy in his current role. He attributes his newfound happiness to a paradigm shift towards serving others, a realization sparked by… Two Tall Guys Talking Sales Podcast – The Power of Service: How Giving Back Can Drive Sales Success featuring Jim Hardwick, Chief Community Officer of Sales Xceleration – Episode 31