Leadership – Page 3

Two Tall Guys Talking Sales – Amy Connor discusses Salespeople vs. Lead Generation: Are You Using Your Team Wisely? – E125

By Sean O'Shaughnessey

How do you measure the success of your sales and marketing efforts? If you’ve ever wondered whether your marketing dollars are driving revenue or if your sales team is making the most of their leads, this episode is for you.

Kevin Lawson and Sean O’Shaughnessey sit down with Amy Connor, founder of CMO on Loan, to discuss how marketing and sales should work together for growth. Amy brings her extensive experience from Procter & Gamble, Luxottica, and other top brands to help mid-market companies build marketing confidence, align with sales, and drive measurable results.

Key Topics Discussed

The Basketball Analogy: Why Tracking Performance Matters (~00:01:00)
- Just like basketball teams analyze stats post-game, businesses need to measure marketing and sales effectiveness.
How to Decide Between Investing in Sales or Marketing (~00:04:30)
- Business owners often wonder whether they should put more resources into sales teams or marketing initiatives—Amy breaks it down.
Aligning Marketing and Sales for Lead Generation (~00:07:30)
- Should salespeople generate their own leads, or is there a more efficient way to bring prospects to the table?
The Role of a Fractional CMO: How Businesses Can Engage Marketing Leadership (~00:11:20)
- Amy explains how a fractional CMO helps companies make smarter marketing decisions without the full-time executive cost.
A Sneak Peek into Next Week: Measuring Marketing Effectiveness (~00:13:52)
- Tune in next week as Amy shares the tools and strategies that help businesses track what’s working and what’s not.

Key Quotes

Sean O’Shaughnessey (~00:06:41):
“So many of my clients assume that salespeople will find their own leads, but is that really the best use of their time?”
Amy Connor (~00:07:51):
“Your sales team is often being asked to do too much. Something will suffer if they have to hunt for leads and nurture accounts at the same time.”
Kevin Lawson (~00:11:00):
“When companies say, ‘I need more sales,’ what they often mean is, ‘I need more leads.’ But are they solving the right problem?”

Additional Resources

Learn more about CMO on Loan and how they help businesses improve marketing effectiveness: www.cmo-onloan.com
Connect with Amy Connor on LinkedIn: https://www.linkedin.com/in/amyconnor/

A Significant Actionable Item from this Podcast

Evaluate your marketing and sales alignment. Take a step back and ask:

Do I have a clear process for tracking where leads come from and how they convert?
Is my sales team spending too much time prospecting instead of closing deals?
Would marketing support help my business generate higher-quality leads?

If you’re not sure, it may be time to review your funnel and define a strategy that ensures sales and marketing work together—not in silos.

Why You Should Listen to This Episode

This episode is a must-listen for business owners, sales leaders, and marketing professionals looking to make smarter investments in growth. Amy Connor shares real-world insights on how marketing can drive measurable business results and how sales and marketing can function as a united force. Plus, next week’s episode will dive even deeper into how to measure marketing effectiveness, so don’t miss it!

🎧 Download now and take the first step toward a more effective marketing and sales strategy!

Two Tall Guys Talking Sales – Mastering Time Management: Essential Strategies for Sales Managers – E123

By Sean O'Shaughnessey

Time is the most valuable resource for any professional, but for sales managers, it is the linchpin of success. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the critical strategies for effective time management as a sales leader. Whether you’re a new sales manager, an aspiring leader, or a business owner overseeing a sales team, this discussion is packed with insights to help you optimize your calendar, empower your team, and drive performance without falling into the trap of micromanagement.

Key Topics Discussed

The Shift from Salesperson to Sales Manager (00:03:00)
Understanding the common pitfalls new sales managers face when transitioning from an individual contributor to a leadership role.
The Role of a Sales Manager: Player vs. Coach (00:04:00)
Why sales managers must avoid the “player-coach” mindset and instead focus on leading, mentoring, and enabling their team’s success.
Structuring Your Calendar for Maximum Impact (00:05:45)
How to design your weekly schedule to balance coaching, strategy, internal meetings, and team availability while avoiding distractions.
The Power of Shared Calendars and CRMs (00:07:00)
Best practices for leveraging shared calendars and CRM tools to improve communication, transparency, and sales efficiency.
Why Sales Managers Should Be Like Basketball Coaches (00:13:30)
The importance of stepping back and allowing sales reps to take the lead in deals—coaching them rather than closing for them.

Key Quotes

🗣 Sean O’Shaughnessey (00:02:55):
“When you are a sales manager, your job is to make others better. You shouldn’t be stealing deals from your sales reps—you should be empowering them to succeed.”

🗣 Kevin Lawson (00:04:00):
“A player is different from being a coach. Players take direction, coaches give direction. If you’re leading a team, you need to be coaching, not competing.”

🗣 Sean O’Shaughnessey (00:14:00):
“Watch a basketball game and look at the coach. How many times do they step onto the court to take a free throw for their players? Never. That’s how sales management should work too.”

Additional Resources

📘 The One Minute Manager by Ken Blanchard & Spencer Johnson – A classic guide to leadership and effective management.
📅 Book Time with Sean – Need help refining your sales management strategy? Schedule a consultation.

A Significant Actionable Item from this Podcast

Audit Your Calendar and Block Time for Success
Sales managers must structure their schedules intentionally. Take 30 minutes to review your calendar for the upcoming week:
✅ Block out time for coaching your team.
✅ Set aside dedicated slots for strategy and internal meetings.
✅ Ensure your calendar is updated and visible for your team.
✅ Reserve time for proactive sales engagement, like voice-of-the-customer calls.

Making these adjustments will free you from constant firefighting and allow you to lead effectively.

Why You Should Listen to This Episode

If you’re a sales manager—or aspiring to be one—this episode is a must-listen. Kevin and Sean deliver practical, real-world strategies to help you break free from micromanagement, structure your time effectively, and lead your team to success. Stop getting caught up in the weeds and start managing like a pro. Listen now and take control of your sales leadership journey!

🎧 Hit play and start optimizing your sales management strategy today! 🚀

Building Winning Sales Teams for the Future: Insights for CEOs and Sales Leaders

By Sean O'Shaughnessey

What are the key moves that CEOs and sales leaders must make to prepare their teams for success in 2025? That’s exactly what we explored in a recent episode of the Art and Science of Complex Sales podcast hosted by Paul Fuller of Membrain. I had the pleasure of joining Kevin Lawson, President of Lighthouse Sales Advisors, for a deep dive into the strategies defining high-performing sales organizations in the year ahead.

You may recognize Kevin’s name. He is my co-host on the Two Tall Guys Talking Sales podcast. Paul titled our interview with him “Building Winning Sales Teams for the Future with Two Tall Guys.”

In the episode, we uncover the real-world tactics and leadership insights that can help CEOs transform their sales organizations—from defining who to sell to building processes that deliver consistent results. If you’re serious about leading a sales team that thrives amid complexity, I highly encourage you to listen to the full conversation. The link is below—don’t miss it.

Driving Growth Through Data-Driven Leadership

One of the central themes we cover is the role of data in guiding strategic decisions. Successful sales leadership today hinges on the ability to read the right signals—metrics like call volumes, deal velocity, customer life cycles, and attrition rates. We discuss how to turn that data into insights that refine your ideal customer profile (ICP) and strengthen your sales and marketing efforts.

We also discuss how a CEO’s dashboard isn’t static. It must evolve based on the business environment, market pressures, and geopolitical events. Paul Fuller helps steer the conversation into practical territory, where we explore how CEOs can stay ahead by making data-informed decisions and leading their teams with clarity and focus.

This podcast episode will be particularly valuable if you’re a CEO or revenue leader aiming to refine your strategic lens. Be sure to check it out through the link below.

Coaching for Consistent Performance Improvement

Data might show you where to focus, but coaching is what gets you results. Kevin and I discuss the importance of coaching for incremental gains—not just pushing reps to hit more numbers but helping them level up in ability and mindset.

We show how leaders can move salespeople from C-level to B-level performers and beyond through relatable sports analogies and real-world examples. These small, steady improvements compound over time and create a team of confident, capable sellers who know how to win.

We also touch on the need for structured coaching frameworks and repeatable systems, which we provide through website resources. If you lead a team that could benefit from a morale, performance, or accountability boost, this is a conversation you won’t want to miss.

Building a Repeatable, Scalable Sales Process

We close the episode with a focused discussion on sales process discipline. By taking a structured approach to evaluating leads—based on product fit, probability, and alignment with your ICP—leaders can drive better forecasting and higher win rates.

Even modest improvements in key areas like win rate, deal size, and sales cycle length can produce exponential results. We explore how a 7% uptick in core metrics could double your revenue. The message is clear: Clarity, consistency, and customer focus are non-negotiable in 2025.

If you’re looking to future-proof your sales organization, this podcast episode is packed with strategies and examples that can serve as a roadmap. Listen to the full episode and learn how to apply these concepts to your company.

Listen to the Full Episode

This is a powerful episode for CEOs, sales leaders, and anyone responsible for building and leading high-performance sales teams. If you’re ready to equip your team for 2025 and beyond, don’t miss this conversation on the Art and Science of Complex Sales podcast.

🎧 Episode: Building Winning Sales Teams for the Future with Two Tall Guys
🎙 Host: Paul Fuller of Membrain
🔗 https://podcasts.apple.com/us/podcast/building-winning-sales-teams-for-the-future-with-two/id1723340327?i=1000684372709

Click the link to listen now—you’ll walk away with actionable ideas to implement immediately.

Unlock Revenue Growth with a Fractional VP of Sales

By Sean O'Shaughnessey

Are you feeling stuck trying to grow your company’s revenue? Do you find yourself juggling too many responsibilities, struggling with outdated sales methods, or unsure how to take your sales team to the next level? You’re not alone.

Many business owners face these challenges, and at New Sales Expert, we’re here to help.

I’m Sean O’Shaughnessey, founder of New Sales Expert, and we specialize in helping B2B companies accelerate revenue production by implementing proven sales strategies, developing top talent, and creating scalable processes.

In our latest video, I outline how we address some of the most common sales problems business owners encounter, such as:

No formal sales process,
Inaccurate revenue forecasting,
Losing a big customer and not knowing how to recover,
Struggling to hire and retain the right salespeople.

As a Fractional Vice President of Sales, we work alongside business owners to provide expert leadership and guidance. Here’s how we do it:

Assessing your current sales team and processes.
Defining winning strategies with clear metrics for success.
Building accurate forecasting tools for long-term planning.
Hiring and developing top-performing sales talent.

We operate on a fractional basis, allowing us to bring discipline, accountability, and focus to your sales organization without the full-time cost. Our detailed Scope of Work outlines clear schedules and timelines, ensuring sustained execution and measurable results.

Ready to accelerate your revenue growth? Watch the full video to learn more about how we can help your business thrive.

📌 Contact us today for a free consultation at www.NewSales.Expert.

Let’s build a culture of sales success and drive the growth your business deserves.

Driving Sales Performance with Strategic Competitive Analysis

By Sean O'Shaughnessey

Ever wonder why some sales teams consistently outperform their competitors while others struggle to close deals? The answer often lies in how well they understand and leverage competitive analysis in their sales process.

Let’s talk about competitive analysis in sales. It’s not just about knowing your competition – it’s about understanding how to use that knowledge to drive results. You need to grasp why prospects choose specific solutions over others and, more importantly, why they sometimes choose to do nothing at all.

Have you considered how many deals you’ve lost not to competitors but to indecision? These “no decision” outcomes often stem from a fundamental gap in prospect qualification. Intelligent sales professionals dig deeper, asking targeted questions about organizational priorities, resource allocation, and strategic initiatives. They understand that timing can be just as crucial as the solution itself.

The modern sales landscape demands a sophisticated approach to competitive analysis. Your success hinges on aligning your organization’s strengths with your prospect’s needs. But here’s the real question: Do you truly understand what your ideal client values most?

Many sales professionals miss the mark by focusing solely on feature comparisons. While product capabilities matter, they’re just one piece of the puzzle. The real power lies in understanding how your solution addresses your prospect’s challenges. This requires a comprehensive view of your competitive landscape, including direct and indirect competitors.

Think about your last few lost deals. What patterns emerge when you analyze the feedback? Every objection and hesitation after presenting pricing are valuable data points that should shape your competitive strategy. Your sales conversations must reflect a deep understanding of your prospect’s value metrics.

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Turning Competition into Opportunity: A Guide for Success in Sales

By Sean O'Shaughnessey

Competition in B2B sales isn’t your enemy. It’s your greatest catalyst for growth and innovation in today’s dynamic market landscape. Have you considered how viewing competitors as opportunities rather than threats could transform your sales approach? Let me show you why this mindset shift matters for your bottom line.

Think beyond the obvious when identifying your competition. Your real rivals aren’t just companies selling similar products or services. They’re anyone competing for your prospect’s budget allocation. This includes businesses offering solutions with capabilities or price points different from yours and other priorities within the prospect. The competitive landscape extends far beyond your direct market segment.

The most formidable opponent often lurks in the shadows of customer inertia. This “no-decision” competitor manifests as your prospect’s resistance to change. It’s the comfort zone that whispers, “Maybe later,” or “What we have works fine.” Understanding this psychological barrier is crucial for your sales strategy.

You need a systematic approach to analyzing and outmaneuvering your competition. Start with an honest assessment of your position in the market. What unique value do you bring to your customers? Where do you consistently outperform others? This self-awareness forms the foundation of your competitive strategy.

Know your competition inside and out. Study their strengths, weaknesses, market positioning, and customer relationships. Your competitive analysis must go deeper than surface-level observations. Map out how their strengths align with your weaknesses. This intelligence helps you craft more compelling value propositions and sales approaches.

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From Micro-Manager to Leader: Fostering Growth in Your Sales Team

By Sean O'Shaughnessey

Are you unknowingly sabotaging your sales team’s success? The answer might surprise you. The actual cost of micromanagement extends far beyond immediate productivity concerns.

Trust forms the bedrock of every high-performing sales organization. Yet many sales leaders unconsciously undermine this foundation through micromanagement. You’ve seen the signs – constant check-ins, questioning every decision, and hovering over your team’s shoulders. The culture you’ve worked so hard to build is slowly eroding.

Your best salespeople are leaving. Team morale is plummeting.

Let’s be clear about what constitutes micromanagement in sales. It’s not about being involved or interested in your team’s work. The real issue emerges when you start dictating every move and creating an atmosphere of constant surveillance.

Consider the cost of replacing top sales talent in today’s market. Beyond the substantial financial investment, you’re losing institutional knowledge and client relationships. Your organization can’t afford this drain on resources, and the impact reverberates throughout your entire sales ecosystem.

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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 representing remarkable privilege. These resources fundamentally transform our ability to build, scale, and succeed in business. The American business environment provides exceptional advantages that deserve recognition. Our infrastructure, legal frameworks, and market access create a foundation for entrepreneurial success. We benefit from systems that foster recovery and growth, even during challenging times. Consider our robust network of support services, educational resources, and professional opportunities.

Practicing intentional gratitude strengthens our leadership capacity and business perspective. Before your Thanksgiving celebration, take time to acknowledge the mentors, partners, and team members who’ve contributed to your journey. Recognize the systems and opportunities that enable your business operations. This reflection goes beyond mere sentiment—it builds resilience and shapes strategic thinking.

The business landscape presents significant challenges, and many professionals face personal struggles during the holiday season. Loss, isolation, or business setbacks can make the celebration feel difficult. The strength of our business community lies in supporting each other through these moments. Professional networks should extend beyond business transactions to genuine human connections.

Our position in the global business ecosystem carries both privilege and responsibility. While pursuing growth and innovation, we must maintain perspective on our advantageous starting point. The American business environment, despite its challenges, offers unprecedented opportunities for those willing to pursue them.

The holiday season provides a natural pause point for strategic reflection. Use this time to evaluate your position within the broader business landscape. Appreciate the resources, relationships, and opportunities that support your professional journey. This awareness strengthens your leadership capacity and business perspective. The privilege of operating in the American business environment extends beyond material advantages. It includes access to knowledge, networks, and opportunities for continuous growth. These assets represent extraordinary value in the global context. Our awareness of these advantages should inform our business decisions and leadership approaches.

Professional success intertwines with personal well-being. The strength of our business community depends on supporting each other beyond traditional business relationships. Reach out to your professional network with a genuine interest in their well-being. Strong communities build resilient businesses.

This Thanksgiving, let’s move beyond surface-level appreciation to meaningful recognition of our business advantages. The American entrepreneurial ecosystem provides extraordinary opportunities for growth and success. Acknowledging these advantages strengthens our capacity for effective leadership and sustainable business growth.

Contact me if you need support. Genuine connection and mutual support strengthen our shared success.

May your Thanksgiving celebration provide both rest and perspective for the journey ahead.

Happy Thanksgiving!

Two Tall Guys Talking Sales – Sales Intelligence 101: Using AI and Networking to Target Ideal Customers – E112

By Sean O'Shaughnessey

Welcome to another compelling episode of Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O’Shaughnessey! Kevin and Sean dive deep into a central challenge for sales teams: identifying ideal customers and building a robust prospect list. In this episode, they uncover practical strategies, share indispensable tools, and illustrate how a strong grasp of your customer can turn prospects into loyal clients. Whether you’re part of a lean sales team or managing large territories, this episode is loaded with insights to help you grow.

Key Topics Discussed

Building Your Prospect List (approx. 2:00): Kevin introduces the concept of creating an ideal prospect list and breaks down the importance of strategic targeting beyond mere proximity or broad industry fit.
Activating and Leveraging Networks (approx. 3:00): Both hosts discuss the value of networking to uncover warm referrals, emphasizing the need to build a customized, one-to-one outreach strategy.
Effective Tools for Targeting Customers (approx. 4:45): Sean and Kevin highlight essential tools like LinkedIn Sales Navigator, KnowledgeNet, and AI-powered tools like Perplexity to streamline the process of finding and qualifying leads.
Understanding the Customer’s Goals and Structure (approx. 7:20): Sean shares a story about understanding internal company dynamics and how knowing a prospect’s structure and goals helps in creating value-oriented solutions.
Actionable Research Insights (approx. 10:15): The duo dives into practical research techniques to understand client organizations and stakeholders, stressing that informed sellers are empowered sellers.

Key Quotes

Kevin: “To build a good prospect list, it doesn’t have to mean endless hours on Google or hundreds of cold calls. With the right tools, you can have a list ready before lunch.” (approx. 5:55)
Sean: “Your job isn’t just to sell a product; it’s to solve a problem. When you start with that goal, the sale becomes almost inevitable.” (approx. 14:40)
Kevin: “Whether you’re a team of one or a team of five, using the tools at hand to maximize your reach and impact makes you competitive.” (approx. 13:00)

Additional Resources

A Significant Actionable Item from this Podcast

Leverage AI-powered tools to gain deeper insights into target companies and individuals before engaging in outreach. By using resources like Perplexity to understand a client’s structure, goals, and decision-making processes, salespeople can craft highly personalized solutions that add immediate value.

In the episode, Sean challenged people to use Perplexity to research his fellow co-host, Kevin Lawson. Here is that Perplexity search: https://www.perplexity.ai/search/can-you-help-me-with-informati-Hdjvd9OgQTWFXrODrlhHnQ

In this episode, Kevin and Sean clarify that sales is about more than products—it’s about partnerships. Discover how to empower yourself with the right tools, refine your approach to prospecting, and bring authentic value to each client. Tune in to Two Tall Guys Talking Sales for actionable strategies to transform how you engage, connect, and close.

From Chaos to Order: Improve Your Sales Productivity with Effective Pipeline Management

By Sean O'Shaughnessey

Sales is a complex and intricate world, a jigsaw puzzle where each piece must fit perfectly to create a successful picture. This is especially true when it comes to managing sales, whether you’re a salesperson, a sales manager hoping to enhance your leadership skills, or a CEO in the trenches of a small company. Understanding the challenges and nuances of the sales process is crucial to increasing revenue and productivity.

Imagine you’re in a room full of sports equipment scattered everywhere, from basketball shoes to cheerleading pom-poms. It’s a total mess, and you can barely see the floor. This is a perfect metaphor for what a disorganized sales pipeline can look like. It’s messy chaotic, and there’s always something that doesn’t quite smell right.

The sales pipeline is vital for tracking and managing sales prospects from the initial contact to the deal’s closing. It visually represents where potential customers are in the sales process. However, if not properly managed, the pipeline can become a mess.

A common issue is when a deal gets pushed from one month to the next. The sales rep simply changes the closing date, making it seem like procrastination has become a part of the process. This can be due to various reasons, such as a lack of commitment from the customer, the sales rep not understanding the customer’s needs, or simply a lack of follow-up. To avoid this, it’s essential to go back to basics. Understand where the customer is in their evaluation and buying process. Are they genuinely interested in buying or just exploring the idea? It’s perfectly fine for a customer to be in the exploratory stage, but that doesn’t mean they’re ready to buy. These customers should be considered early-stage prospects and not be rushed into buying.

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