Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

You’ll eventually hit a wall if you’re running a sales organization—or wearing multiple hats as founder, CEO, and sales manager. That wall is often invisible until growth stalls, key deals slip through the cracks, or your top salesperson burns out. So, what’s the next move? It’s not more hustle. It’s assessment.

A sales assessment isn’t about checking boxes. It’s about understanding where you are, how you operate, and what’s holding you back. Too many small business leaders assume they’re doing fine because revenue is growing or the team is hitting their quotas. But are you growing at the rate your market allows? Are your sales activities aligned with your long-term goals? Are you building a repeatable system, or are you just getting lucky?

Let’s get tactical. A sales plan isn’t just a revenue target. It’s your go-to-market strategy. It defines your audience, your message, and your motion. It answers why you’re talking to those prospects and what value you’re bringing to them. Without a plan, you’re reacting instead of executing. You’re chasing leads instead of building a pipeline.

If you’re a small company—perhaps under $30 million in revenue—and selling into a national market, chances are your market potential is hundreds of millions, maybe billions. That means your market share is a rounding error, which means there’s room to grow. The question is: Are you operating in a way that allows you to capture that growth?

Even if you’re running lean, you should benchmark your performance against top-tier organizations. Not because you’re competing with them directly, but because they set the standard. What are they doing that you’re not? Where are they more efficient? How do they structure their teams? You’re leaving money on the table if you’re not asking those questions.

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Two Tall Guys Talking Sales – Know Your Numbers: A Sales Leader’s Guide to Growth Metrics – E132

Two Tall Guys Talking Sales – Know Your Numbers: A Sales Leader’s Guide to Growth Metrics – E132

As Q2 kicks into full gear, it’s time to pause and reflect—are you ahead, on pace, or falling behind on your sales targets? In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey unpack one of a sales leader’s most crucial yet often overlooked responsibilities: knowing your numbers. With equal parts practical advice and strategic vision, this conversation walks you through the foundational metrics every sales leader should track—customer acquisition cost, average transaction size, support staffing ratios, and more. Whether you’re forecasting growth, scaling headcount, or simply trying to stay ahead of the competition, this episode is your playbook for building a metrics-driven sales organization that thrives.

Key Topics Discussed

  • Why “Keeping Score” Matters in Sales Leadership (00:00)
    Kevin kicks off the episode with a strong analogy to competitive sports, emphasizing that tracking performance metrics is non-negotiable for sales leaders aiming to grow.
  • Building a Forward-Looking Sales Metrics Matrix (00:01)
    Kevin walks through how to build a simple but powerful matrix using transaction volume, average deal size, and headcount to visualize both current performance and future goals.
  • Calculating Average Transaction Size and Quota Coverage (00:02)
    Learn how to reverse-engineer quota achievement by dividing sales goals by average transaction size to determine activity targets for your team.
  • Understanding Customer Acquisition Cost (CAC) (00:05)
    Sean breaks down the components of CAC and explains why every sales leader must know this figure to scale sustainably and profitably.
  • Debunking the “Geopolitics Are Killing Sales” Excuse (00:09)
    Sean challenges the notion that global events are valid reasons for missed quotas, reinforcing that internal execution and strategic clarity are what really matter.
  • Aligning Sales Activity with Strategic Growth Goals (00:12)
    Kevin closes the episode with a systems-thinking approach to leadership, showing how small adjustments in metrics, team development, and compensation can drive exponential growth.

Key Quotes

Kevin Lawson: “Keeping score is important. Really important. I’m talking like March Madness. Final game. Important.” (00:00)

Sean O’Shaughnessey: “If it takes you more than 20 minutes to figure out this information, then you need a better bookkeeping system.” (00:06)

Sean O’Shaughnessey: “You need to know what your average deal size is. You need to know how long it takes you to get a customer. Your CRM should be solving that.” (00:07)

Kevin Lawson: “We want to gently steer our company towards our goals. So the thinking about this process is all about knowing your numbers.” (00:12)

A Significant Actionable Item from this Podcast

Build Your Sales Metrics Matrix This Week
Start with your annual revenue goal. Break it down by the number of salespeople, average transaction value, and number of transactions needed per rep per month. Then layer in your customer acquisition cost, support staffing ratios, and expected margin. This matrix becomes your roadmap for scaling intelligently—whether you’re doubling headcount, expanding territory, or just trying to hit a consistent quota.

Episode Summary

In a world of uncertainty, Two Tall Guys Talking Sales reminds us that clarity comes from data. Kevin and Sean deliver a compelling, no-nonsense discussion about how to take control of your revenue engine by genuinely understanding the math behind your sales motion. Whether you’re a CEO, VP of Sales, or just starting to lead a team, this episode offers an essential primer on aligning your operations to your goals. Don’t miss this one—it might be the wake-up call your spreadsheet has been waiting for.

👉 Hit play now to future-proof your sales strategy by learning how to know your numbers like a pro.

Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

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 a sales executive interested in how sales performance impacts company valuation, this episode delivers invaluable guidance. It’s part education, part strategy session, and all high-value insight.

Key Topics Discussed

  • The Three Core Approaches to Business Valuation – Asset, income, and comparative market methods explained simply and practically. (04:22)
  • Preparing a Business for Sale: Lessons from Real Estate – Why “curb appeal” matters for companies and how to improve it over time. (07:36)
  • What Buyers Want: Sales Growth, Consistency, and Processes – How prospective buyers assess the health of a business beyond profit margins. (09:00)
  • The Hidden Red Flag: When the Owner Is the Only Salesperson – Risks for buyers and strategies for mitigating dependency on the founder. (13:31)
  • Leveraging AI to Gain Competitive Market Intelligence – How technology is transforming buyer and seller knowledge in M&A. (11:32)

Key Quotes

Tom Gottlieb: “Every buyer wants the same thing: a business that works without the owner. That means strong processes, steady sales growth, and predictable profitability.” (09:01)
Sean O’Shaughnessey: “So if you don’t want to stick around after the sale, then train your sales team now—and watch the value of your company go up.” (14:16)
Kevin Lawson: “Tom, every time we talk, I walk away with something new. This episode is no exception.” (11:31)
Tom Gottlieb: “Buyers rarely show up with a bag of cash. There’s a timeline. A deal doesn’t close in a weekend—it’s often a year-long journey.” (07:00)

Additional Resources

A Significant Actionable Item from this Podcast

Start documenting your sales process today.
If you are a business owner—or advise one—and the majority of revenue hinges on a single salesperson (often the owner themselves), that’s a red flag for any future buyer. Begin formalizing your sales process, distribute responsibilities among team members, and track sales metrics consistently. This improves operational resilience and significantly enhances company value in a potential sale.

Why You Should Listen to This Episode

Selling a business isn’t just about profit, perception, process, and preparedness. In this episode, Kevin and Sean extract wisdom from Tom Gottlieb that applies to any B2B organization considering an exit in the next 3 to 10 years. It’s packed with strategic takeaways, sales insights, and behind-the-scenes truths about what makes a business attractive to buyers. Whether you’re a founder, an investor, or a sales leader, this episode will reshape how you think about long-term value creation. Tune in and learn how to make your business sell-ready—starting now.

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

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.

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Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

Welcome back to another episode of Two Tall Guys Talking Sales with Kevin Lawson and Sean O’Shaughnessey! This week, we’re diving deep into measuring marketing effectiveness with special guest Amy Connor, founder of CMO OnLoan. If you’ve ever struggled to connect marketing strategies to real business results, this episode is for you. Grab your marketing colleague and tune in—understanding what’s working (and what’s not) in your marketing is the key to driving sales growth.

Key Topics Discussed:

  • The Importance of Measuring Marketing Performance (01:08)
    Many companies don’t effectively track their marketing impact. Amy shares how focusing on key metrics—without overwhelming dashboards—can create a direct path to success.
  • Sales and Marketing Must Be Aligned (02:09)
    Customers don’t see marketing and sales as separate—they see one company. Amy explains why integrating both functions is crucial for a seamless customer journey.
  • Why Vanity Metrics Don’t Matter (02:55)
    Impressions, clicks, and leads may look impressive, but if they don’t translate to business results, they don’t matter. Learn how to focus on meaningful data that connects to revenue.
  • The Billboard Advertising Myth (03:12)
    Can a billboard drive B2B sales? Amy and Sean discuss the realities of traditional advertising and why small businesses should think critically about marketing spend.
  • Aligning Sales Messaging with Marketing Content (05:57)
    Sales teams shouldn’t be the only ones communicating key messages. Amy shares why marketing content must reinforce what salespeople say to build trust and shorten sales cycles.
  • Tactical vs. Strategic Marketing – What’s the Right Balance? (08:29)
    Should your marketing focus on brand awareness or immediate sales action? Amy explains the difference and how to measure each effectively.

Key Quotes:

Amy Connor: “Marketing and sales are part of the customer’s journey in a united way. The customer doesn’t see ‘marketing did this and sales did that’—they see the company as a whole.” (01:45)

Sean O’Shaughnessey: “Salespeople start at a disadvantage because buyers inherently don’t trust them. That’s why marketing must reinforce their message to build credibility.” (05:40)

Kevin Lawson: “Up to 70% of the buyer’s journey happens before they talk to sales. If marketing isn’t working ahead of time, you’re already losing.” (07:52)

Additional Resources:

  • Visit CMO OnLoan for free marketing resources: www.cmo-onloan.com
  • Connect with Amy Connor on LinkedIn: Amy Connor LinkedIn
  • Listen to the first episode featuring Amy: Last Week’s Podcast: https://podcasts.apple.com/us/podcast/amy-connor-discusses-salespeople-vs-lead-generation/id1668686029?i=1000693738159

A Significant Actionable Item from this Podcast:

Audit Your Marketing Metrics
Take 30 minutes this week to assess what marketing data your company is tracking. Are you focusing on impressions and clicks or lead conversion and revenue impact? Identify one metric that directly connects marketing activity to business growth and make it your priority.

Why You Should Listen to This Episode

Marketing is more than just branding—it’s a revenue-driving function. In this conversation, Amy Connor unpacks how B2B companies can measure what truly matters, align sales and marketing, and ensure every dollar spent on marketing contributes to the bottom line. If you want your marketing efforts to drive real sales results, don’t miss this insightful discussion. Tune in now!

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

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

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

Unlock Revenue Growth with a Fractional VP of Sales

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

Driving Sales Performance with Strategic Competitive Analysis

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

Turning Competition into Opportunity: A Guide for Success in Sales

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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Unlocking Sales Success: The Power of KPIs in Sales Processes

Unlocking Sales Success: The Power of KPIs in Sales Processes

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?

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