Two Tall Guys Talking Sales – The Four Buckets of Sales Growth with Steve Wittal

Two Tall Guys Talking Sales – The Four Buckets of Sales Growth with Steve Wittal

By Sean O'Shaughnessey

In this dynamic episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome Canadian SalesXceleration expert Steve Wittal for an in-depth look into the foundations of effective sales strategies. Steve brings decades of experience in startup advisory, sales management, and business growth, sharing a robust framework that simplifies complex growth challenges into four digestible buckets: desirability, clarity, predictability, and deliverability. If you’re a business leader looking to strengthen your sales processes, sharpen your messaging, or improve revenue generation, this conversation is a goldmine.

Key Topics Discussed

  • The Power of Leadership in Change Management (~01:02)
    Steve opens by explaining why leadership is the starting point for any growth initiative, especially when change is involved.
  • The Four Buckets Framework for Growth (~03:00)
    Steve outlines his method for diagnosing and resolving growth issues by focusing on four pillars: desirability, clarity, predictability, and deliverability.
  • Desirability and Understanding the Customer’s Pain (~04:00)
    Why identifying whether your product is a “must-have” or “nice-to-have” is critical to sales success.
  • The Importance of Clarity and Quantifying the Cost of Inaction (~06:39)
    Sean and Steve unpack how clarity in messaging and value proposition can move buyers from indecision to action.
  • Predictability, Scalability, and Sales Playbooks (~09:20)
    How aligning your sales process with the customer’s buying journey enables scale and drives predictable revenue.
  • Deliverability and the Voice of the Customer (~10:50)
    Steve emphasizes the importance of retention, early wins, and referrals as indicators that your solution truly delivers.

Key Quotes

  • Steve Wittal: “A problem well-defined is a problem half-solved. Before we prescribe, we have to truly understand.” (~02:46)
  • Kevin Lawson: “When you’ve dotted all those i’s, it makes you a market-facing product. That’s how you achieve market fit.” (~13:25)
  • Sean O’Shaughnessey: “When a customer comes to you and says, ‘Can you help me solve this?’ — that’s sales nirvana.” (~08:35)

Additional Resources

  • Connect with Steve Wittal on LinkedIn – https://www.linkedin.com/in/stevewittal/
  • Steve’s email: Steve Wittal <swittal@salesxceleration.com>

A Significant Actionable Item from this Podcast

Audit Your Sales Strategy Through the Four Buckets.
Take a moment to evaluate your organization’s performance across Steve’s four key areas:

  • Desirability: Is your product essential or optional to your buyers?
  • Clarity: Can your team articulate your value proposition in a way that resonates with prospects and highlights the cost of inaction?
  • Predictability: Do you have a repeatable sales process that aligns with how your customers buy?
  • Deliverability: Are you consistently delivering on promises and capturing client feedback to validate success?

This self-assessment will uncover gaps in your current sales approach and point to immediate areas for improvement.

Summary

Whether you’re leading a startup or managing a growing sales team, this episode delivers a concise yet powerful framework for achieving sales success. Steve Wittal’s “Four Buckets” offer practical, business acumen–driven insights that will help you reframe your growth strategy and improve every stage of your sales process. If you’re serious about improving revenue generation and becoming a trusted advisor in your client relationships, don’t miss this episode. Tune in now and transform your approach to value selling.

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…
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?

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Balancing Act: Networking, Direct Prospecting, and Customer Referrals for Revenue Growth

Balancing Act: Networking, Direct Prospecting, and Customer Referrals for Revenue Growth

By Sean O'Shaughnessey

Is your sales pipeline running dry? We’ve all been there.

Let me share a personal story that might resonate with you. After spending months securing a major deal, I found myself staring at an empty pipeline. The celebration of landing that giant whale quickly became a stark reality check. This experience taught me an invaluable lesson about sustainable sales growth.

Revenue generation isn’t just about closing deals—it’s about maintaining a consistent flow of opportunities. Your success depends on mastering the art of prospecting, yet many salespeople struggle with this fundamental skill. Are you dedicating enough time to building your pipeline, or are you caught in the feast-and-famine cycle?

The most effective sales professionals understand that prospecting isn’t a one-dimensional activity. Think of your prospecting strategy as a carefully orchestrated symphony, where different elements work together to create a harmonious result. Direct outreach and network-based approaches each play their unique roles in this composition.

Visualize a three-legged stool symbolizing the three-pronged approach to sales: networking and referrals, direct prospecting, and existing customers. Each of these legs supports growing your business and consistently achieving your revenue goals.

Consider how a software company might approach this dual strategy. While tracking metrics for direct outreach is straightforward, measuring networking success requires a different lens. How many new relationships have you cultivated? Which dormant connections have you rekindled? These indicators matter just as much as your cold call statistics.

I recently spoke with a consulting professional who shared an interesting perspective on networking metrics. Rather than counting sales pitches, he measures success by the number of times he naturally introduces his services in conversations. This subtle shift transforms aggressive selling into educational opportunities. Have you considered how this approach might work in your context?

Your prospecting strategy must align with your target audience’s expectations and behaviors. Waiting for inbound leads isn’t a strategy—it’s a recipe for inconsistent results. When you prospect through your network, the goal isn’t to ask for immediate business. Instead, you’re planting seeds for future opportunities through strategic introductions.

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Two Tall Guys Talking Sales – Sales Planning 101: How to Crush Your Quota and Grow New Accounts – E108

Two Tall Guys Talking Sales – Sales Planning 101: How to Crush Your Quota and Grow New Accounts – E108

By Sean O'Shaughnessey

Welcome back to Two Tall Guys Talking Sales! In this episode, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the nuts and bolts of individual sales planning. This conversation moves beyond just hitting quotas—it’s about creating a personal strategy that drives you toward success. Whether you’re starting fresh in a new fiscal year or planning for growth, Kevin and Sean have you covered with actionable advice, real-world examples, and inspiration for developing your own winning sales plan. Get ready to sharpen your tools and plan to exceed your quota!

Key Topics Discussed

  • Building Your Sales Plan (2:00): Sean breaks down the critical elements of creating your personal sales plan, including setting a quota, calculating the number of deals you need to close, and how to push yourself beyond expectations.
  • Analyzing Your Existing Customer Base (4:10): Kevin emphasizes the importance of understanding your existing customers, maintaining relationships, and strategically growing accounts that can carry you through the year.
  • Knowing Your Competitors and Market (6:30): Both hosts discuss the significance of competitor analysis and knowing your market, down to the behaviors and needs of your customers.
  • Planning for New Accounts (9:00): Sean challenges listeners to add new accounts to their plan and start treating those prospective clients like they are essential to your financial future.
  • Collaborating with Marketing (11:00): Sean and Kevin stress the importance of working hand-in-hand with your marketing team to fill the gaps in your sales plan and generate quality leads.

Key Quotes

  • Sean (2:50): “If you’re supposed to do 50 deals to hit your million-dollar quota, guess what? You have to do 60. We’re going over quota—no excuses!”
  • Kevin (4:40): “Am I taking care of the customers that I know I should be taking care of? Yes or no. It’s really straightforward.”
  • Kevin (5:50): “Know who your competitors are, and know who you want to do business with. Don’t just rely on marketing to tell you—figure it out for yourself.”
  • Sean (9:55): “You need to think of these prospective accounts as your best friends. If they are important to your success, know everything about them.”

Additional Resources

  • If you missed last week’s episode on Building a Sales Plan That Works: Aligning Vision with Execution, go back and listen for an in-depth look at building sales strategies from a leadership perspective. https://sites.libsyn.com/458454/site/building-a-sales-plan-that-works-aligning-vision-with-execution

A Significant Actionable Item from this Podcast

Identify 20 new accounts you do not currently have a relationship with and begin learning everything about them—competitors, pain points, goals, and market behaviors. Integrating these targets into your sales plan today can set you up for growth and success as early as January.

Summary

This episode of Two Tall Guys Talking Sales is packed with valuable insights for every sales professional looking to take control of their personal sales plan. Kevin and Sean encourage you to meet your quota and exceed it by going the extra mile—analyzing existing customers, targeting new ones, understanding your competitors, and working closely with marketing to generate leads. Whether you’re an individual salesperson or a sales leader, this conversation will leave you energized and ready to tackle the coming months with a winning strategy. Don’t miss this episode!

Two Tall Guys Talking Sales Podcast – Sales Success and Growing Pains: How to Build Systems That Scale – E104

Two Tall Guys Talking Sales Podcast – Sales Success and Growing Pains: How to Build Systems That Scale – E104

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey explore the complexities of rapid sales growth. While many companies aspire to grow, not all are ready for the operational strain accompanying success. The hosts share insights on scaling systems, optimizing sales operations, and ensuring growth doesn’t break your business. This episode offers actionable strategies for businesses facing fast-paced expansion, from onboarding salespeople to expanding infrastructure.

Key Topics Discussed:

  • Recognizing the Pain of Growth (00:01:00)
    Sean discusses the challenge of managing growth when sales outpace operational capabilities, posing critical questions about when to add resources like marketing or legal support.
  • Building Systems That Scale (00:02:30)
    Kevin shares how building robust, repeatable processes—whether hiring one salesperson or ten—ensures sustainable and scalable growth.
  • When to Hire Sales Support Staff (00:03:32)
    The discussion highlights the importance of adding operational roles such as sales analysts or revenue operations personnel to ease the workload on sales teams.
  • Maximizing Sales Efficiency (00:07:14)
    Sean advises identifying which tasks to delegate from high-performing salespeople to specialists, increasing overall efficiency and productivity.
  • Tailoring Sales Strategy to Industry Needs (00:09:26)
    Kevin elaborates on how different industries may require unique sales strategies, emphasizing the need to adapt based on business size and market demands.

Key Quotes:

  • Sean: “We need to grow, but can the rest of the organization grow with us?” (00:05:00)
  • Kevin: “Growth is a cash event. Growth is a change event. When you 2x, 3x a business in sales, you often break things.” (00:02:48)
  • Sean: “Think about how much time high-performing people spend doing things that are not high-performing tasks, and figure out how you can take that off their plate.” (00:12:52)

A Significant Actionable Item from this Podcast:

Conduct a time audit for your sales team. Identify non-sales tasks that consume their time, such as data entry or order processing. Delegate these tasks to a dedicated admin or sales operations role. This can significantly boost productivity and allow your top performers to focus on closing deals.

Summary:

In this episode, Kevin and Sean break down the key challenges of scaling a business during periods of fast growth. They offer practical advice on creating efficient processes, hiring the right support staff, and ensuring your sales operations keep pace with your revenue expansion. Whether your company is rapidly expanding or preparing for future growth, this episode is packed with actionable insights that can help you maintain momentum without breaking your business. Tune in to learn how to balance growth and efficiency for long-term success!

Crafting a Sales Process Flowchart: Visualize the stages in your sales process for consistency – Driving New Sales: Transforming Small Businesses into Sales Powerhouses – Episode 9

Crafting a Sales Process Flowchart: Visualize the stages in your sales process for consistency – Driving New Sales: Transforming Small Businesses into Sales Powerhouses – Episode 9

By Sean O'Shaughnessey

Welcome to “Driving New Sales: Transforming Small Businesses into Sales Powerhouses,” the essential podcast for B2B sales professionals, managers, and CEOs of companies aiming for revenue growth. In today’s episode, we’re diving into the core of any thriving sales organization: the Sales Process Flowchart. Guided by Sean O’Shaughnessey, a veteran in sales strategy, we’ll explore how to craft and refine your sales process for peak efficiency and effectiveness.

Our esteemed sponsor, Kevin Lawson of Lighthouse Sales Advisors and Sales Xceleration, is our sponsor for this episode. Kevin offers unparalleled sales leadership solutions for small businesses, focusing on navigating sales growth challenges and scaling up operations through his extensive experience. Kevin’s fractional consultancy is the answer for those looking for expert guidance in sales team development without the commitment of a full-time executive.

Contact Kevin:
Email: Kevin@lighthousesalesadvisors.com
LinkedIn: linkedin.com/in/kwlawson

Key Topics Discussed

  • Blueprint of Success: Discover the importance of having a well-defined Sales Process Flowchart as your guide through the sales journey.
  • Stages of the Sales Process: Sean breaks down each stage of the sales process, from prospecting to nurturing long-term relationships.
  • Customizing Your Sales Approach: Learn the significance of tailoring your sales process to fit your unique business model and industry requirements.
  • Visualizing the Sales Funnel: An exploration of how visualizing your sales funnel can identify potential leaks and optimize the sales journey.
  • Leveraging Technology: Insight into how automation tools and CRM systems can enhance your sales process and free up your team to focus on selling.
  • The Dynamic Nature of Sales Processes: Emphasizing the importance of continuous feedback and adaptation to keep your sales process relevant and effective.

Key Quotes

  • “Success doesn’t come from random acts of effort. It requires a blueprint, a master plan that orchestrates every step of the sales journey.”
  • “Imagine your Sales Process Flowchart as the architectural plan for a skyscraper. Without it, you’re merely stacking bricks without knowing how high they should go.”
  • “Technology is the wind beneath our sales team’s wings, freeing them up to do what they do best—sell.”

Additional Resources

  • Sales Management Association Study: Highlights the performance impact of using a formal sales process.
  • Harvard Business Review Study: Shows a significant revenue increase for businesses with a standardized sales process.

Action Items You Can Do Today

  • Develop a Visual Sales Process Flowchart: Start with a simple outline and refine it to suit your team’s needs.
  • Solicit Feedback from Your Sales Team: Use their frontline insights to improve your sales process.
  • Customize Your Approach: Ensure your sales stages align with your business model for increased efficiency.
  • Invest in Training and Technology: Equip your team with the necessary knowledge and tools to excel.
  • Embrace Continuous Improvement: Regularly update your sales process based on feedback and changing market conditions.

Today’s episode with Sean O’Shaughnessey has armed you with the knowledge to construct a Sales Process Flowchart that is the backbone of a successful sales strategy. Implementing the discussed actionable strategies will refine your sales process, making it a powerful engine for business growth. Stay tuned for more insightful episodes to further empower your journey to becoming a sales powerhouse.

Contact Information

  • Sean O’Shaughnessey: Email – Sean@NewSales.Expert

For more expert advice on transforming your sales strategies, don’t forget to subscribe to “Driving New Sales: Transforming Small Businesses into Sales Powerhouses.” Join us next time for another deep dive into the strategies that can elevate your sales game. Until then, keep selling smart and forging meaningful connections with your customers.