entrepreneur

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!

Build a Repeatable Sales Process Using Buyer Personas

by Sean O'Shaughnessey

In the world of sales, consistency is a cornerstone for success. Salespeople, sales managers, and CEOs alike strive to find a sustainable way to grow their business, and one effective strategy is to focus on buyer personas. Identifying and understanding these personas can streamline the sales process, making it easier to target the right customers and tailor your approach to meet their specific needs.

Consistency is key. When you consistently sell to profitable companies that see value in your solutions, you can standardize your sales processes and messaging. This consistency allows you to tweak and improve your methods incrementally, rather than making wild changes that may not lead to profitability. Many small companies don’t have the luxury of unlimited cash flow. They need to be mindful of their line of credit and ensure that their accounts receivable don’t get out of hand. By focusing on companies that are easy to sell to and where your product or service fits seamlessly, you can make your clients successful and maintain a steady growth trajectory.

The entrepreneurial operating system (EOS) is a valuable framework that helps businesses achieve consistency. By setting firm foundational corners, such as data, people, and core processes, businesses can create a structured environment where everyone can succeed. For sales departments, this means formalizing not only the messaging but also the reporting structure, job descriptions, core goals, and key behaviors. Consistency in these areas leads to reliable and repeatable results.

A repeatable sales process is crucial. If everything is custom, nothing is standardized, and this can lead to chaos. Sales leaders must set the standard for consistency, and both business owners and salespeople need to align themselves with these consistent behaviors. Standardizing the sales process enables better forecasting and a more predictable customer flow.

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The Revenue Operator: Using AI to Sell More Strategically in B2B

by Sean O'Shaughnessey

AI will not replace strong B2B sellers; it will surface whether you operate as a transaction manager or as a revenue operator who shapes decisions, reduces risk, and aligns stakeholders.

Benjamin Todd wrote a great article, “How not to lose your job to AI.” Todd’s four skill categories land cleanly in sales because they map to how buyers buy: the work that matters most is the work that is hardest to automate, hardest to teach, and most leverageable when friction is removed. The implication is straightforward. Your job is to let AI absorb volume and repetition, while you concentrate on judgment, orchestration, and credibility in the moments that actually move a deal.

The operating model: Use AI to compress effort, then reinvest the capacity into decision-shaping

Most reps will use AI to “do more” of the same activities. That produces activity inflation, not differentiation. The advantage comes from shifting your time and attention into the parts of the cycle where outcomes are decided: problem definition, executive alignment, risk control, and commercial negotiation.

That’s the practical bridge between Todd’s categories and daily execution:

Hard-to-automate skills become your primary value delivery system: executive communication, political navigation, situational judgment.
Deployment-related skills become your productivity engine: workflow configuration, automation, tool integration, and governance.
Scarce, high-utility skills become your multiplier: leadership, strategy, opportunity planning, talent development.
Hard-for-others-to-learn skills become your moat: persuasion, storytelling, consultative diagnosis, entrepreneurship.

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Beyond Quotas: Elevate Your Sales Strategy with Continuous Coaching

by Sean O'Shaughnessey

Salespeople often rely on short-term tactics to hit their numbers. But what if the difference between mediocrity and excellence isn’t in the last-minute push, but in the way we plan, coach, and lead throughout the year? Many sales managers treat coaching as a reactive measure, something they do when performance drops. That’s a missed opportunity.

Proactive coaching isn’t just about fixing issues. It’s about enhancing potential.

The best salespeople in the world, much like top athletes, have coaches. Not because they’re failing, but because they’re trying to be even better. If your top rep is hitting quota, that’s not the finish line. That’s the starting point for the next level of performance.

Sales leaders often default to focusing on the bottom performers. That’s necessary, but incomplete. High performers need guidance, too. Not to be micromanaged, but to be challenged. Ask yourself: What are you doing to help your top performers improve? If the answer is “not much,” you’re leaving growth on the table.

There’s a tactical way to approach this.

Most companies conduct quarterly business reviews with customers. The same structure can be flipped inward and used as a coaching tool. Instead of asking what happened last quarter, ask what could happen next. What would success look like in the next 90 days? What challenges need to be addressed before they become problems?

This isn’t about adding another meeting to everyone’s calendar. It’s about intentional planning. One-to-one conversations that go deeper than pipeline reviews. The goal is to align on strategy, identify gaps in skills or processes, and develop a roadmap for improvement. Done right, it drives accountability and engagement simultaneously.

Salespeople often say they want more training. But training without context falls flat. Coaching provides that context. It’s individualized, relevant, and ongoing. It also sends a message: your development matters. That message builds loyalty. It also improves performance.

If you’re a CEO or founder managing your own sales or leading a small team, this applies even more. You’re not just the closer, you’re the coach. Your team’s performance will reflect your commitment to their growth.

Are you investing time to help them get better?
Or are you too busy chasing deals to build a repeatable system?

Coaching doesn’t have to be complicated.

Begin by evaluating three key areas:

network,
skills,
metrics.

Does your rep have enough network reach to generate leads? Do they have the tactical skills to progress deals? And are you tracking the right metrics to measure performance, not just outcomes? If any of those are unclear, that’s your starting point.

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B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

Hard-to-automate skills
Deployment-related skills
Scarce, high-utility skills
Skills hard for others to learn or replicate

Each of these aligns tightly with the demands of modern B2B sales.

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Two Tall Guys Talking Sales – Patrick O’Donnell Explains How to Hire and Onboard Sales Talent That Actually Performs – Episode 139

by Sean O'Shaughnessey

In this high-impact episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome sales acceleration expert Patrick O’Donnell to tackle one of the toughest challenges facing small business CEOs: hiring and onboarding top-performing sales talent. Together, they dive deep into proven sales strategies that help CEOs find strong candidates and keep them engaged, successful, and driving revenue. If you’ve ever hired a salesperson who didn’t work out, or you’re planning to…

Why Americans Should Be Thankful This Thanksgiving

by Sean O'Shaughnessey

As Thanksgiving approaches, the season offers a powerful moment to recognize our extraordinary position in the global business landscape. As business leaders, entrepreneurs, and professionals, we operate within a framework of unprecedented opportunity and abundance, and this reality deserves our attention and appreciation. Our daily business operations rely on technological capabilities that much of the world’s population cannot access. Each time we open our laptops, join virtual meetings, or process digital transactions, we leverage tools…

The Right Person in the Right Seat: Unleashing Company Growth through Strategic Sales Leadership

by Sean O'Shaughnessey

A recurring issue for small companies has emerged; the company’s owner or CEO often leads the sales department. This might be because they believe no one else can sell their product or service better than they can. However, this mindset might be hampering the company’s growth potential.

If you’re a company owner or CEO who leads sales, it’s crucial to consider the risk of this approach. When the person leading the company also heads sales, the business is constrained by the amount of time that leader has. If your salespeople consistently wait for your input or response, you might face a growth opportunity and a challenge simultaneously.

The solution lies in de-risking your organization’s growth potential by getting a sales leader in the sales leadership seat separate from you. This concept resonates with the theory of constraints, a principle often applied in the manufacturing industry but equally applicable in sales. The theory of constraints focuses on identifying the factors that limit your success.

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Unlocking Growth: How TriState Fabricators Transformed Their Sales Approach

by Sean O'Shaughnessey

Have you ever wondered how a well-established manufacturing company can revolutionize its sales strategy? The journey of TriState Fabricators, a premier metal fabrication shop in the Midwest, offers compelling insights into this process. In a recent interview, I sat down with Joe Vogt, President and Owner, and Jonathon Padial, VP of Sales, to discuss their transformative experience. With his 20-year tenure at TriState, Joe Vogt recognized the need for change to scale the business. The…

Two Tall Guys Talking Sales – Mastering Sales Compensation: Strategies for Business Growth – Episode 58

by Sean O'Shaughnessey

Don’t miss out on this episode if you’re looking to revamp or create a sales compensation plan that truly works. Kevin and Sean offer a comprehensive guide that covers everything from the timing of releasing plans to aligning them with your business goals. Tune in to Two Tall Guys Talking Sales and equip yourself with the knowledge to build a compensation plan that not only retains but also attracts top sales talent. Start setting your sales team—and your business—up for success today!

Elevating Your Sales Operations with New Sales Expert

by Sean O'Shaughnessey

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,…