Two Tall Guys Talking Sales – Fixing the Funnel – Building a Sales Pipeline That Actually Works – E130

Two Tall Guys Talking Sales – Fixing the Funnel – Building a Sales Pipeline That Actually Works – E130

By Sean O'Shaughnessey

Welcome back to Two Tall Guys Talking Sales with hosts Kevin Lawson and Sean O’Shaughnessey. In this episode, the tall guys dive deep into one of the most critical yet commonly broken elements in any sales organization: the sales funnel. Whether you’re stuck with a clunky three-stage process that tells you nothing or overwhelmed with 35 micro-stages that only confuse your reps, Sean and Kevin offer a practical guide to rethinking and rebuilding your pipeline strategy. Packed with metaphors (yes, even superhero ones) and sharp analysis, this episode will leave you inspired to take a hard look at your funnel—and finally fix it.


Key Topics Discussed

  • Why Most Sales Funnels Are Broken (00:00:45)
    Sean unpacks the common pitfalls in how companies define and manage their sales stages, including oversimplified or overly complex CRM setups.
  • Defining Sales Stages Based on the Buyer Journey (00:04:30)
    Kevin emphasizes the need to align your sales stages with how buyers actually buy—not how your company wants to sell.
  • How Many Sales Stages Are Too Many? (00:05:00)
    The guys explore the delicate balance between not enough insight and too much complexity in stage design.
  • The Case for Multiple Pipelines (00:08:00)
    When does it make sense to separate budgetary planning pipelines from active sales discussions? Kevin and Sean explain.
  • What a Healthy Funnel Actually Looks Like (00:10:45)
    Sean introduces a visual and mathematical approach to evaluating whether your funnel is properly shaped—and what to do if it’s not.


Key Quotes

“The Avengers became a team, not just Iron Man. You need to have a team. Even superhero salespeople like to have support.”
— Sean O’Shaughnessey (00:02:50)

“Fixing the funnel starts visually. Does it fit well on one sheet of paper? If not, you’ve already lost the battle for clarity.”
— Kevin Lawson (00:04:45)

“Stages should be built to qualify someone into the next step—not just to log an activity. Every transition should represent progress, not busyness.”
— Kevin Lawson (00:06:15)

“If your pipeline doesn’t look like a funnel, then you’re either wasting time or losing deals. Probably both.”
— Sean O’Shaughnessey (00:12:20)

Additional Resources Referenced

A Significant Actionable Item from this Podcast

Audit Your Sales Funnel for Shape and Stage Effectiveness
Pull a report from your CRM and visualize your current pipeline by number of deals and total revenue per stage. Does it actually look like a funnel? If it doesn’t, dig deeper. Are your stages aligned with your buyer’s journey? Are reps stuck in certain stages too long? This snapshot identifies gaps and opportunities for stage redefinition or activity refinement.

Summary

Whether managing a sales team or closing deals yourself, this episode of Two Tall Guys Talking Sales gives you the blueprint to diagnose and repair a misaligned funnel. Sean and Kevin combine humor, hard truths, and highly actionable insights to help you bring structure and sanity back to your sales process. If you’re ready to create a pipeline that reflects how buyers buy—and helps your team win more deals—this episode is a must-listen.

🎧 Listen now and take the first step in fixing your funnel for good.

Two Tall Guys Talking Sales – Sales Prospecting: Are You Chasing Leads or Cultivating Success? – E127

Two Tall Guys Talking Sales – Sales Prospecting: Are You Chasing Leads or Cultivating Success? – E127

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive into the art of sales prospecting using an unusual but powerful analogy—chasing butterflies versus building a garden. Are you tirelessly running after leads or cultivating an environment where ideal prospects naturally come to you? Learn how to create a long-term strategy for consistent revenue growth by positioning your business as the go-to solution for your ideal customers.

Key Topics Discussed:

  • The Butterfly Effect in Sales (00:01:00) – The difference between chasing every lead and strategically attracting the right ones.
  • Building a Sales Garden (00:02:49) – Developing a long-term strategy that consistently nurtures and attracts the best-fit prospects.
  • Marketing & Content Strategy Alignment (00:04:22) – Collaborating with marketing to ensure the right messaging.
  • The Value of Inbound Leads (00:06:11) – Why leads that come through your marketing efforts are often easier to close and more profitable.
  • Tactical Steps for Sales Leaders (00:08:00) – Actionable insights for sales managers to help their teams attract, engage, and convert better.
  • Crafting a Strong Value Proposition (00:10:18) – The foundation of effective lead generation and how to align it with your ideal customer profile.

Key Quotes:

  • Sean O’Shaughnessey (00:01:52): “If you’re hungry for revenue, you’re probably running around chasing butterflies. But if you want sustainable growth, you need to create an environment where prospects naturally come to you.”
  • Kevin Lawson (00:03:55): “Sales leaders, think about your team—have you equipped them with butterfly nets, or have you taught them how to build a garden?”
  • Sean O’Shaughnessey (00:06:44): “The best prospects aren’t the ones you chase—they’re the ones who find their way to your garden because you’ve built something valuable for them.”

Additional Resources:

A Significant Actionable Item from this Podcast:

If you rely solely on outbound prospecting, evaluate your value proposition and content strategy today. Align your marketing and sales teams to ensure your messaging is clear, consistent, and tailored to your ideal buyer. Identify gaps in your digital presence and take the first step toward creating a sales garden that nurtures and attracts the right leads.

Final Thoughts:

Sales is more than just chasing down deals—it’s creating an ecosystem where prospects feel drawn to your expertise, insights, and solutions. In this episode, Sean and Kevin explain shifting from frantic outbound prospecting to a methodical approach that fosters sustainable revenue growth. Whether you’re a sales leader or an individual contributor, you’ll walk away with practical steps to build your high-converting sales garden.

Tune in now and take your sales strategy to the next level!

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!

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

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

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!