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:
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!
Several months ago, I was serving as a fractional VP of Sales for a $50 million manufacturing company. Their top salesperson was a 15-year veteran who knew the industry inside and out. Yet he was consistently being outsold by a competitor’s much newer hire. At first, it didn’t make sense until we discovered the reason. The competitor’s rep wasn’t just more energetic or aggressive. They were AI-enabled. While my client’s rep was manually scrolling LinkedIn…
In this compelling episode, co-hosts Kevin Lawson and Sean O’Shaughnessey delve into the crucial distinctions between workflows, automations, and artificial intelligence (AI), and why understanding these differences isn’t just technical trivia, but foundational to improving sales processes, enhancing sales management, and accelerating revenue generation. If you’re a sales leader, business owner, or B2B rep striving to improve how you use technology to boost sales success, this episode is a must-listen. Packed with real-world examples and…
Is artificial intelligence coming for your sales job? Not if you understand the power of business acumen, value selling, and strategic adoption of tools that amplify, not replace, human expertise. In this high-impact episode of Two Tall Guys Talking Sales, Kevin and Sean tackle the loud claims of AI-induced layoffs with a grounded, practical message for salespeople and sales managers: evolve or fall behind. This is not a doomsday episode; it’s a wake-up call, a…
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.
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:
Each of these aligns tightly with the demands of modern B2B sales.
Read the rest of the article…In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome business intermediary Tom Gottlieb of Berkshire Hathaway. Tom brings decades of experience in buying, selling, and valuing businesses across the Midwest. The conversation dives deep into what truly drives the value of a company—and how sales leaders and business owners alike can prepare their organizations for a future transition. Whether you’re a business owner considering a sale or…
Building an effective sales pipeline requires a shift in strategy. Traditional cold calling has become increasingly ineffective, with decision-makers ignoring unsolicited calls and emails.
In the spring of 2021, Bank of America Corp.’s Merrill Lynch Wealth Management unit banned trainee brokers from making cold calls. According to the Wall Street Journal, it is hard to succeed with cold phone calls in an era when no one picks up. Merrill executives said personal referrals lead to a response around 40% of the time, but less than 2% of people who are cold-called even answer the phone.
Sales teams must adopt a more strategic approach, focusing on relationships rather than volume-based outreach. The key is leveraging existing networks to create warm introductions, significantly improving engagement rates and overall success.
Cold outreach has become expensive and inefficient, and the time spent dialing numbers, leaving voicemails, and sending emails that never get opened results in diminishing returns. Many executives no longer answer unknown calls, and email filters automatically sort cold outreach into spam. Even when messages get through, recipients are skeptical, assuming they are generated by automation rather than a genuine human connection. In reality, sales professionals must find a better way to reach their target audience.
Relationship-based selling offers a more effective alternative. Salespeople should focus on leveraging their connections instead of reaching out to strangers. This approach involves identifying key contacts who can provide warm introductions to potential prospects. These “super connectors” are individuals with strong networks and the ability to facilitate meaningful introductions. By tapping into these relationships, sales teams can bypass the skepticism associated with cold outreach and start conversations with credibility.
Read the rest of the article…Cold calling is dead—or so claims our guest, Ben Victorica, in this thought-provoking Two Tall Guys Talking Sales episode. Hosts Kevin Lawson and Sean O’Shaughnessey dive deep with Ben into the challenges of modern sales pipelines and explore why traditional outreach methods are no longer effective. Together, they uncover how relationship selling, fueled by emotional intelligence and strategic connections, is reshaping the future of sales. Whether you’re a seasoned sales professional or just starting out,…
Are your sales KPIs helping your team succeed? Many sales leaders focus solely on closed deals. This narrow view misses crucial elements of sustainable sales growth.
The journey matters more than the destination. Sales excellence follows a similar path. Your team’s daily actions and behaviors create the foundation for lasting success.
Effective sales measurement requires a comprehensive view of your team’s activities. Top performers consistently execute vital behaviors that drive results. They prospect strategically, nurture relationships, and expand their presence within existing accounts. These leading indicators paint a clearer picture of future performance than lagging metrics alone.
Your KPI framework must evolve beyond historical analysis. Forward-looking metrics help you spot opportunities and challenges before they impact revenue. What’s happening in your pipeline right now? How are your teams finding new prospects? Which accounts show growth potential?
Experience levels significantly impact appropriate performance measures. New salespeople face different challenges than seasoned veterans. A rookie might need help with fundamental sales behaviors while learning your company’s approach. They need clear operational guidance and structured metrics that reinforce proper execution.
Veteran salespeople bring established skills and proven track records. Their KPIs should emphasize continuous improvement and cultural alignment. How are they advancing their capabilities? What value do they add to the broader sales organization?
Read the rest of the article…This episode of Two Tall Guys Talking Sales is a must-listen for anyone looking to future-proof their business. Kevin and Sean offer practical advice and actionable strategies to help you streamline operations, adopt cutting-edge technologies, and align your team for success. Whether you’re planning for 2025 or 2035, the insights shared in this episode will set you on the path to achieving your goals.
Are you still relying on trade shows as your primary sales driver? The sales landscape has undergone a seismic shift. Those packed convention halls and endless rows of booths no longer serve as the bedrock of business development they once were.
Let’s talk about what works in today’s sales environment. Building an effective outbound pipeline isn’t just an option anymore – it’s your survival toolkit. But here’s the challenge: how do you stand out in a market where everyone’s fighting for attention?
Your unique value proposition makes all the difference. Yet many sales professionals miss a crucial point: your value proposition isn’t static. What resonates with a manufacturing client might fall flat with a distribution company. Have you tailored your message to address each industry’s pain points?
Think about your last prospecting campaign. Did you give up after four or five attempts? Research shows it takes 12 to 16 touches before prospects typically respond. This gap between persistence and practice often determines success or failure in modern sales.
The game has changed. Your prospects live in an omnichannel world. They check email between Zoom calls, scroll LinkedIn during lunch, and scan their phones throughout the day. How are you showing up in their digital world?
Consider this: every unanswered email or phone call might be a messaging problem. Are you talking about your features when you should be solving your prospects’ problems? Your prospects don’t care about your product specifications. They care about their challenges, their goals, and their bottom line.
Read the rest of the article…