Stop Guessing. Start Assessing: The First Step Toward Sales Growth

Stop Guessing. Start Assessing: The First Step Toward Sales Growth

By Sean O'Shaughnessey

Are you feeling stuck in your sales organization? You’re not alone. Many founders, CEOs, and sales leaders eventually hit an invisible wall—a growth plateau. Key deals slip away. Your top salesperson, who carries far too much weight, starts to burn out.

In these moments, the instinct is often to push harder. But what’s needed isn’t more hustle. It’s clarity. And clarity starts with a strategic sales assessment.

What a Sales Assessment Means

Too often, leaders see assessments as formalities—checklists that confirm what they already believe. That’s a mistake. An accurate sales assessment is diagnostic. It reveals what’s working, what’s broken, and what’s missing.

Revenue growth doesn’t always mean you’re on the right path. Many companies are growing despite misalignment, not because of strategic execution. Are your sales activities aligned with your market opportunity? Are you pursuing the right prospects with the right message? Or are you just getting lucky?

Read the rest of the article…
Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

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

By Sean O'Shaughnessey

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.

Read the rest of the article…
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

By Sean O'Shaughnessey

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

By Sean O'Shaughnessey

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/

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

By Sean O'Shaughnessey

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!

Unlocking Sales Success: The Power of KPIs in Sales Processes

Unlocking Sales Success: The Power of KPIs in Sales Processes

By Sean O'Shaughnessey

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

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. 

Read the rest of the article…
Designing Sales Compensation Plans That Drive Performance

Designing Sales Compensation Plans That Drive Performance

By Sean O'Shaughnessey

The success of any sales-driven organization in the business-to-business (B2B) space hinges on the sales team’s compensation plan. Over my four decades in B2B sales, I’ve observed that nothing influences the performance of sales personnel more directly than the design and implementation of their compensation plans. Compensation is not merely about rewarding sales achievements but crafting a strategy aligning individual salespeople’s goals with the company’s broader objectives.

A well-structured compensation plan acts as both a motivator and a guide. It compels sales teams not only to meet but exceed their targets, fostering an environment where continuous improvement is not just encouraged but becomes a natural byproduct of the system. For small business CEOs, understanding this dynamic is critical for sustaining and driving growth. Sales compensation is more than just a cost; it’s an investment in the company’s future.

In any sales environment, whether the market is brimming with potential or tightly contested, the compensation plan must be a living document that evolves in response to market conditions, company goals, and team performance. With this adaptability, companies can avoid stagnation or regression in their market positions. As businesses strive to scale and adapt, constructing a compensation plan that genuinely drives the right behaviors becomes all the more pertinent.

To delve deeper into this vital subject, CEOs should consider the immediate impacts of their compensation strategies and their long-term implications on sales culture and employee retention. For those ready to explore the intricacies of effective sales compensation and ensure their strategies are well-suited to their specific business contexts, I am here to lend my expertise. With extensive experience tailoring compensation plans to enhance sales productivity and company profitability, I invite you to reach out for further guidance on crafting a plan that meets and exceeds your strategic goals. You can set a time to talk to me using my link above Book Appointment With Sean.

Read the rest of the article…
The Dashboard Difference: Transforming B2B Sales with Data-Driven Insights

The Dashboard Difference: Transforming B2B Sales with Data-Driven Insights

By Sean O'Shaughnessey

A sales dashboard in business-to-business sales is pivotal for guiding sales teams toward success. This methodical approach to tracking and interpreting data illuminates the path to revenue scaling and fosters a culture of achievement and recognition within an organization.

At its core, a sales dashboard transforms raw data into actionable insights. For salespeople, sales managers, and CEOs of small companies, understanding the nuances of the dashboard can be the difference between stagnation and growth. The key is to develop dashboards that serve the executive leadership, sales managers, and salespeople, ensuring everyone is aligned and moving towards common goals.

The essence of an effective dashboard lies in its ability to reflect both the company’s strategic objectives and its sales force’s individual contributions. It is a balancing act of capturing relevant metrics while also celebrating successes, large and small. For instance, while revenue might be the most apparent indicator of success, the underlying drivers of those revenues—such as the number of first conversations, demos, or site visits—are equally important. These metrics offer a deeper insight into the sales process and are indispensable for a nuanced dashboard. They also offer insights into predictive behavior that will result in increased revenue.

However, dashboards are not just about tracking sales activities. Effective dashboards track not only the quantity but also the quality of efforts. By identifying which events lead to meaningful interactions and ultimately to sales, companies can allocate their resources more wisely.

A sales dashboard enables sales teams to recognize patterns and trends that might otherwise go unnoticed. For example, understanding the conversion rate from demos or proofs of value can highlight areas of the sales process that need refinement. Similarly, tracking the frequency of interactions with prospects can help ensure that potential deals do not fall through the cracks due to neglect.

Despite the apparent complexity, the principle behind dashboarding is straightforward: what gets measured gets managed. By meticulously tracking the right metrics, sales teams can focus on activities that drive success. This approach improves the efficiency and effectiveness of the sales process and aligns the sales team’s efforts with the company’s strategic objectives.

A sales dashboard is invaluable for any sales organization aiming to elevate its performance. By capturing and analyzing the right data, companies can gain insights into their sales process, identify opportunities for improvement, and celebrate successes. As the sales landscape continues to evolve, the ability to adapt and optimize through dashboarding will remain a critical determinant of success.

Immediate actions that you can do today

  1. Audit Your Current Sales Dashboard: Review your existing sales dashboard to ensure it aligns with your strategic goals and effectively tracks leading and lagging sales success indicators. Identify any gaps in data collection, particularly around the quality of interactions, conversion rates, and networking efforts. If you find areas lacking in insights or if certain activities are not being tracked, make a plan to integrate these into your dashboard. This step ensures that your sales team is focused on activities that directly contribute to revenue growth and customer engagement.
  2. Implement a Routine Dashboard Review Process: Establish a routine, whether daily, weekly, or monthly, for your sales team to review dashboard metrics together. This meeting should focus on analyzing the data for patterns, trends, and actionable insights that can drive strategic decisions. Use this time to celebrate wins, identify areas for improvement, and adjust strategies as needed based on the dashboard’s data. Encouraging open discussion around the dashboard metrics fosters a culture of continuous improvement and team alignment toward common sales goals.
Maximizing Sales Performance: The Critical Importance of Compensation Planning

Maximizing Sales Performance: The Critical Importance of Compensation Planning

By Sean O'Shaughnessey

In B2B sales organizations, ensuring a robust sales force capable of adapting to market fluctuations and corporate objectives is paramount. Among the myriad factors contributing to sales teams’ success, two elements emerge as particularly crucial: the design and timely dissemination of compensation plans.

At the heart of a well-oiled sales organization lies the principle of trust, a currency of immense value in building a healthy sales culture. Transparency and punctuality in rolling out compensation plans are not merely administrative duties but foundational to establishing trust within the sales team. As we edge closer to the end of the year, the urgency of having these plans in place by January 1 cannot be overstated. Delays in distributing compensation details not only seed doubt and uncertainty but can significantly impede the sales momentum critical in the initial months of the fiscal year.

Understanding the weight of this responsibility, it’s imperative for CEOs, CFOs, and sales managers to appreciate the broader implications of compensation plans on the sales organization’s trust. These plans serve as a tangible manifestation of the company’s priorities and a roadmap for sales personnel to align their efforts with overarching business goals. More than a mere outline of potential earnings, they encapsulate strategic objectives, incentive mechanisms, and performance expectations.

In crafting these plans, it is essential to consider holistically the company’s strategic direction, market positioning, and the sales force’s role in realizing corporate ambitions. Compensation plans should not only reflect a company’s immediate revenue objectives but also its long-term growth aspirations. They ought to incentivize behaviors that align with the company’s strategic initiatives, such as penetrating new markets, enhancing customer retention, or diversifying product portfolios.

Moreover, the process of developing and communicating these plans must be imbued with clarity, foresight, and empathy. It’s not enough to dictate terms; there must be a dialogue—a genuine effort to convey the rationale behind compensation structures, changes, and expectations. This transparency ensures that sales professionals are not just recipients of a policy but active participants in a shared mission.

Timing plays a crucial role in this equation. The goal of distributing compensation plans well before the year’s end cannot be understated. This preemptive approach allows for necessary dialogues, adjustments, and mental preparations, ensuring that sales teams hit the ground running come January 1. Such punctuality respects the personal and professional timelines of sales personnel and signals the organization’s respect for their role and contributions.

In essence, creating and disseminating thoughtful, timely compensation plans are fundamental to cultivating a motivated, aligned, and high-performing sales team. These plans are not static documents but living agreements that reflect the dynamic interplay between a company’s vision and its most valuable asset—its people. As businesses navigate the complexities of market environments and strive for growth, the strategic alignment facilitated by well-conceived compensation plans becomes an invaluable lever for success.

Immediate actions that you can use

Focusing on actionable strategies is key to making theoretical knowledge practical and impactful. Here are immediate action items readers can implement today to enhance their sales organizations:

  1. Review Your Current Compensation Plans:
    • Take a detailed look at your existing compensation structures. Are they aligned with your current business goals and market dynamics? This initial review is crucial for identifying areas that need adjustment or complete overhaul.
    • Action: Gather your sales leadership team for a briefing on current compensation structures. Initiate a discussion on how they align with company goals and market conditions.
  2. Set a Clear Timeline for the Roll-out of New Plans:
    • Establish a firm deadline for the new compensation plans to be communicated to the sales team. A good practice is to aim for a distribution date well before the new fiscal year begins, allowing time for feedback and questions.
    • Action: Draft a project timeline today that includes key milestones like plan finalization, team briefing sessions, and the deadline for official roll-out.
  3. Initiate Open Dialogues with Sales Teams:
    • Transparency and communication are vital in ensuring the sales team’s buy-in for the new compensation plans. Start conversations with your sales team about their current challenges and expectations for the upcoming plans.
    • Action: Schedule a series of feedback sessions or one-on-one meetings with sales representatives over the next week to gather input and address concerns regarding compensation plans.
  4. Align Compensation Plans with Strategic Goals:
    • Ensure that the new compensation plans are not just numbers but are strategically designed to drive the behaviors and outcomes that align with the company’s long-term objectives.
    • Action: Convene a meeting with key stakeholders in sales, finance, and strategic planning today to ensure the alignment of compensation plans with the company’s strategic goals.

Implementing these action items promptly can significantly enhance the effectiveness of your sales team, align efforts with strategic goals, and foster a culture of trust and motivation within your organization.