buyer persona

Turning Around Sales Performance: Strategies for CEOs and Sales Managers to Foster Internal Alignment

By Sean O'Shaughnessey

Navigating a sales turnaround isn’t just about fixing numbers; it’s about transforming the business. It’s about realigning expectations, rebuilding internal trust, and creating a structured, sustainable path forward.

If you’re a CEO, sales manager, or a key salesperson in your organization, the pressure to reverse a sales slump can feel overwhelming. However, the truth is that turnarounds aren’t made in a sprint; they’re built through clarity, consistency, and effective communication.

Too often, sales leaders make the mistake of focusing only on the downward trend. They get caught up in the urgency of the numbers and forget that the real challenge lies in managing upward, setting expectations with executive leadership, and aligning them with reality.

If your sales team is underperforming, your internal stakeholders are your new audience. Just as with external prospects, you need to manage their expectations with a clear, actionable plan.

The process starts with a shift in mindset.

Instead of viewing upper management as critics, think of them as clients. What do they need to believe in this turnaround? What information do they need to trust your leadership? Start by building a high-level outline. Avoid over-engineering the details in the early stages. Focus on where you want to go, then reverse-engineer the steps to get there.

Every turnaround starts from a rear position. That means your first job is to stop the downward momentum. Before you can scale revenue, you need to stabilize it. That requires a clear definition of success, agreed upon by everyone involved.

Are you trying to double revenue in 12 months?
Or just return to last year’s baseline?
Is that goal realistic given your market, team, and resources?

If not, revise it. A stretch goal is fine. A fantasy is not.

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

By Sean O'Shaughnessey

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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Understanding Your Customers: The Role of Buyer Personas and Quarterly Business Reviews

By Sean O'Shaughnessey

Want to know the real secret behind successful sales? It’s not just about knowing what your customers need. The true power lies in understanding who they are at their core.

Have you ever wondered why some sales professionals consistently outperform their peers? The answer often comes down to their mastery of buyer personas and detailed profiles that capture the essence of your ideal customers.

Think of buyer personas as your secret weapon in the sales battlefield. These aren’t just random customer profiles thrown together in a rushed afternoon meeting. They represent carefully crafted composites of your most valuable clients, built from real-world data and insights. Your company might need several of these personas, each targeting different market segments with laser precision.

Creating effective buyer personas demands more than just surface-level observation. Start with a thorough analysis of your business landscape. Examine your strengths and weaknesses. Map out the opportunities that excite you and the threats that keep you up at night. This foundation helps you understand exactly where you fit in your customers’ world.

What makes your top customers tick? The answer lies in meaningful conversations with your best clients. These discussions should dig deep into both quantitative and qualitative factors. Demographics tell part of the story – age, position, education, family status. But the real gold comes from understanding their motivations. Why did they choose you? What problems do you solve that keep them coming back?

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Two Tall Guys Talking Sales Podcast – Scaling from Your First 10 Customers to 50, 100 and Beyond – Episode 54

By Sean O'Shaughnessey

If you’ve got your first 10 customers and are wondering, “What next?” then this episode of Two Tall Guys Talking Sales is essential listening. Hosts Kevin Lawson and Sean O’Shaughnessey explore the transformational journey from acquiring your first customers to scaling up your business. Dive into critical topics like product-market fit, market messaging, the role of the CEO as a salesperson, and much more. Arm yourself with practical, real-world advice to take your business to the next level.

Key Topics Discussed

The Crucial Jump from 10 to 50 Customers

Kevin and Sean examine the strategic shift required when you’re looking to grow from 10 customers to a more substantial customer base. They stress the importance of formalizing and aligning your offering with a well-defined buyer persona.

Understanding Buyer Personas

A recurring topic was the art and science of buyer personas. Kevin emphasizes the need to revisit and revise these as your business evolves. The objective is to understand who you’re selling to and what problem you’re solving for them.

Sales Leadership & Standardization

Sean explores the standardization of sales processes and offerings, particularly for scaling from a one-person operation to a multi-person sales team. This standardization is crucial for scalability and profitability.

The Role of the CEO in Sales

The hosts delve into the inevitable shift in the sales role of the CEO as the company grows. While the CEO might be heavily involved in sales initially, scaling to 50 or 100 customers requires a dedicated sales team.

Selling Tools vs. Selling Solutions

Sean provides a compelling analogy between selling tools and selling solutions. He emphasizes the importance of selling a standardized product rather than a customizable toolkit, using historical examples like Henry Ford and Steve Jobs.

Key Quotes

Kevin: “One challenge I see here that sales leaders need to solve is how to formalize and standardize the attraction process.”

Sean: “You need to really start focusing on who do you sell to, what problem do you really solve, and how do you sell this thing so that other people can sell for you.”

Summary

Don’t miss this episode if you’re gearing up for rapid growth. Both Kevin and Sean provide actionable insights that will equip you to transition from a startup to a scalable business. With a blend of theoretical knowledge and real-world advice, they lay down a roadmap for you to follow. Whether you’re a CEO doing sales, a startup looking to break into the market, or a sales leader aiming for standardization, this episode is your guide to elevating your sales game. Tune in now to pave the way for your business growth!

Two Tall Guys Talking Sales Podcast – Know Your Customer: Mastering Buyer Personas in Modern Sales – Episode 48

By Sean O'Shaughnessey

Welcome to another episode of Two Tall Guys Talking Sales with your hosts, Kevin Lawson and Sean O’Shaughnessey. In this riveting episode, we take a deep dive into the often talked about but seldom mastered topic: Buyer Personas. Whether you’re listening on a Tuesday drive back home or on a Wednesday morning commute to work, this episode is packed with actionable insights to set you up for the rest of your week, month, and quarter. Tune in to find out how to create accurate buyer personas that can help you make smarter sales and marketing decisions.

📝 Key Topics Discussed:

Defining Buyer Personas: Kevin and Sean explore what a buyer persona really is and why it’s crucial for sales success.
The Importance of SWOT Analysis: Kevin explains that creating a buyer persona isn’t a one-off task; it begins with understanding your SWOT (Strengths, Weaknesses, Opportunities, and Threats) analysis.
Ideal Client Profiles & Unique Selling Proposition: Why understanding these can help fine-tune your buyer personas.
Digging into Demographics and Psychographics: How to gather and utilize this data to develop detailed buyer personas.
Quarterly Business Reviews (QBRs): Sean shares insights into who should be involved in these reviews and the type of questions that can help enrich your buyer personas.

🗨️ Key Quotes:

“If you’re out there and wondering how to get this process started, thinking that you’ve already done a SWOT analysis…now’s the time to talk about buyer personas.” – Kevin Lawson
“Salespeople are valuable. Salespeople are important to the sales process. And it is your job to teach your company about your customers.” – Sean O’Shaughnessey
“Salespeople are great people day in day out. We shouldn’t have to pay a tax because of bad salespeople doing bad things in the marketplace.” – Kevin Lawson

📚 Additional Resources:

🎧 Why You Should Listen:

Crafting an accurate and effective buyer persona isn’t just a task; it’s an art. This episode provides not only the theory but also the actionable steps you can take to create buyer personas that resonate with your target market. From initial concepts to understanding your customer needs during a QBR, Kevin and Sean have packed this episode with tools you can use immediately. Listen now to avoid the pitfalls and fast-track your way to sales success.

Ready to revolutionize your sales approach? Hit that download button and tune in now! 🎧

Two Tall Guys Talking Sales Podcast – Understanding and Adapting to the Buyer’s Journey for Sales Success – Episode 33

By Sean O'Shaughnessey

In this thought-provoking podcast, hosts Kevin Lawson and Sean O’Shaughnessey dive into the challenges salespeople face when their sales process doesn’t align with the buyer’s journey. Using the example of a beer industry manufacturer, they explore the difficulties encountered when dealing with prospects who are only interested in the price and user count and how this can lead to feeling like a commodity. This insightful discussion underscores the importance of adapting to the buyer’s journey to sell more effectively.

As the conversation continues, Sean and Kevin emphasize the need to understand the buyer’s process, from recognizing the signs of a good prospect to determining the right time to buy. They highlight the importance of asking the right questions, listening to the buyer, and identifying their current position in the evaluation process. The hosts also discuss the concept of commercial teaching, which involves meeting prospects at their level of knowledge about the industry, solution, or product.

In addition, the duo addresses the challenge of long sales cycles and the factors that contribute to them, such as not understanding where the buyer is in their journey or not setting up for success earlier in the sales process. They encourage salespeople to be self-reflective and analyze their pipelines, identifying deals that may be stuck or taking longer than expected due to a lack of alignment with the buyer’s journey.

Furthermore, Kevin and Sean touch upon the importance of knowing the buyer persona, recognizing that different people within an organization have different perspectives and needs. By understanding the type of person you’re speaking with, salespeople can connect more quickly and effectively.

The podcast concludes with a challenge for salespeople to be introspective and consider how they can better align their sales process with the buyer’s journey for improved results.