Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

By Sean O'Shaughnessey

Autumn is the time of year for sales leaders, managers, and CEOs to begin laying the groundwork for next year’s success. Have you considered how your current sales compensation plans impact your team’s motivation and productivity? Now is the ideal moment to evaluate, adjust, and deliver these plans, preferably by December 1st. Doing so can significantly influence your team’s drive to close deals in December and build momentum heading into the next fiscal year.

Sales compensation should be motivating and rewarding for employees. It directly shapes your sales team’s behaviors and priorities. An effective plan incentivizes the right actions and deters the wrong ones.

Consider a common pitfall: salespeople holding back deals to inflate their numbers for the following year. Does your current compensation structure inadvertently reward this practice? If so, you’re unintentionally harming your year-end results.

To counter this, strategically incorporate compensation escalators and cliffs into your plan. Escalators progressively reward increased sales performance throughout the year. Higher performance equals higher commission rates, driving your sales team to push forward continually. 

Commission cliffs reset commission rates at the beginning of each year, creating a sense of urgency to close deals before the end of December. Communicating these compensation details clearly by early December ensures your team understands what’s at stake.

Don’t hold your team back!

Another critical compensation consideration is eliminating commission caps. While some organizations cap commissions to control expenses, this practice can backfire dramatically. Caps tell your top-performing salespeople that their exceptional efforts are neither valued nor rewarded appropriately. This demotivates your top talent and encourages them to seek opportunities elsewhere that offer uncapped rewards. 

Removing commission caps signals that the organization fully supports and rewards outstanding performance. Have you considered how much growth your company might achieve if artificial constraints didn’t limit your sales team?

When evaluating compensation, look beyond simple cost containment. Consider the true profitability of incentivizing increased sales volume. Once salespeople reach their targets and enter accelerators, each additional dollar earned typically comes at a lower incremental cost to your organization. 

Sales transactions earlier in the year have already covered the salesperson’s base salary once they have met their annual quota. In fact, at 100% of quota, the salesperson should have covered all their costs and their share of the overall company’s revenue needs. Thus, every extra sale at escalated commission rates still contributes positively to your overall profitability. 

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Hiring for Growth: How to Build a Sales Team That Drives Long-Term Success

Hiring for Growth: How to Build a Sales Team That Drives Long-Term Success

By Sean O'Shaughnessey

Building a successful sales team requires more than just filling open seats with available candidates. Company leadership must strategically align its hiring process with business objectives, market needs, and long-term goals. 

Whether you’re a solopreneur transitioning to a team-based approach or a CEO managing a growing sales force, the principles of intentional recruitment and onboarding remain the same. Hiring the right people is an investment in the future of your business.

One of the most common pitfalls in sales hiring is a lack of intentionality. Too often, small businesses hire out of convenience, choosing candidates from their immediate network or taking the first person who seems interested. While this approach may solve an immediate need, it rarely leads to long-term success. 

Hiring a salesperson means selecting someone who can actively drive growth and represent your brand with competence and integrity. The stakes are even higher when you’re working with a lean team; every hire matters, and mediocrity is not an option.

To avoid these missteps, it’s essential to approach hiring with the same rigor you apply to your sales process. Think of recruiting as a parallel to securing a high-value client. Just as you wouldn’t sell your product without qualifying leads or understanding their needs, you shouldn’t hire without a structured process to evaluate candidates. 

Begin by defining what success looks like for the role. What skills and attributes are non-negotiable? What specific outcomes do you expect this person to achieve within their first 90 days? A clear job description and measurable KPIs set the foundation for finding the right fit.

Cultural alignment is another critical factor. Your salespeople are the face of your business to prospects and customers. Their ability to embody your company’s values and mission can make or break the customer experience. A candidate might have a stellar track record, but if their approach clashes with your team’s culture, the partnership is unlikely to succeed. At the same time, skills and experience must align with the specific demands of the role. For instance, if your goal is aggressive market penetration, you need a hunter mentality, someone skilled in building relationships from scratch and closing deals in uncharted territory.

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Mastering Sales Channels: How to Align Your Strategy for Maximum Impact

Mastering Sales Channels: How to Align Your Strategy for Maximum Impact

By Sean O'Shaughnessey

Understanding the dynamics of sales channels can transform how businesses approach their markets. Many sales professionals, whether they are salespeople, managers, or CEOs, often miss a critical distinction: the difference between the product they are selling and the value it provides. 

This gap in understanding can lead to suboptimal sales performance, particularly in environments where products are sold through intermediaries, such as distributors, referral partners, or dealer networks. The challenge is not just about knowing your product, but also about understanding how to position it in a way that resonates with every player in the sales chain.

Sales success starts with recognizing who your true customer is. In sales management or channel sales, the end customer is often not the person you interact with directly. Instead, your “customer” might be the intermediary, your distributor, reseller, or even your own sales team. These intermediaries are the ones who ultimately connect your product to its final user. If you don’t understand their challenges, motivations, and context, you risk failing to equip them with the necessary tools to succeed. Are you selling a product’s features, or are you helping them understand how to sell it effectively? This distinction is vital.

When selling through intermediaries, the emphasis should shift from “what the product does” to “how the product can be sold.” Your distributors or referral partners don’t need every technical detail of your product. They need clarity on how it solves problems for their customers, how it fits into their existing offerings, and how they can position it to drive sales. 

The goal is not to overwhelm your partners with information but to provide actionable insights that align with their specific needs. If you’re focusing solely on product features, you’re likely missing the mark.

Salespeople and sales managers must also recognize the game they are playing. Are you selling a commodity, a widely available product, or an exclusive offering? Each scenario demands a different strategy. 

Commodities often compete on price, necessitating bulk sales or value-added services to differentiate themselves. Widely available products often rely on relationships, service quality, or unique add-ons to differentiate themselves. Exclusive products, on the other hand, can often avoid price wars by emphasizing their uniqueness and superior quality. Knowing which game you’re in allows you to tailor your approach and avoid misaligned strategies.

For small businesses and solopreneurs, the challenge lies in effectively managing referral partners. Referral partnerships are a powerful way to generate leads, but they require careful management and oversight. 

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Transforming Quota-Setting: Strategies for Sales Leaders to Optimize Performance and Revenue

Transforming Quota-Setting: Strategies for Sales Leaders to Optimize Performance and Revenue

By Sean O'Shaughnessey

Quota-setting is one of the most misunderstood elements of sales leadership. Too often, it’s treated as a spreadsheet exercise or a top-down directive, rather than a strategic lever that drives behavior, performance, and growth.

Whether you’re leading a team of 20 or you’re the founder managing three reps, how you define quotas has a direct impact on your revenue trajectory and your team’s motivation.

So, where do you start?

With timing. If you’re not delivering quotas to your team until February or March, you’re already behind. Salespeople need clarity by December. That gives them runway to plan, prioritize, and hit the ground running in January. Delayed quotas create confusion and stall momentum. To achieve a strong Q1, you need to equip your team early.

Quota-setting varies depending on the size of your company. Larger teams offer more flexibility. With 10 or more reps, you can spread risk, balance performance, and model averages. You’ll have top performers who consistently overdeliver, alongside newer reps who are still ramping up. The law of averages works in your favor. You can afford some variance. Smaller teams don’t have that luxury.

When you’re running a small team, maybe two or three reps or founder-led sales, every individual matters. One person missing quota can tank your number.

You can’t rely on averages. You need precision.

That means tying quotas to actual relationships, known opportunities, and real probability. It’s not about slicing up a target evenly. It’s about assigning numbers based on what’s realistically achievable in each territory or account list.

Territory design plays a big role here. Whether it’s geographic, vertical, or named accounts, quota must reflect the market potential. You can’t expect equal performance from unequal opportunity. If Rep A has 500 viable accounts and Rep B has 50, their quotas shouldn’t look the same unless you have data that says Rep B’s accounts are closer to your Ideal Client Profile. Use available market data to inform the number. Don’t assign quotas in a vacuum. 

In larger organizations, quotas often originate from the top down, typically from finance. The CEO and CFO commit a growth number to the board, investors, or in public filings to the SEC. They have no choice but to pass it down. It’s not uncommon for the sales team to receive the number without context. That’s a problem. If you’re in a leadership role, you need to pressure test that number. Can your team realistically hit it? If not, what additional resources are required?

  • More headcount?
  • Better enablement?
  • Marketing support?

In large organizations where the quota is driven by investor expectations, the VP of Sales must establish an organization well before the new year that achieves this year’s goal, while also meeting the expectation of growth for the next year. Planning ahead, sometimes years in advance, is part of the job.

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Two Tall Guys Talking Sales – Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows – Episode 144

Two Tall Guys Talking Sales – Future-Proofing Your Sales Career with AI, Strategy, and Smarter Workflows – Episode 144

By Sean O'Shaughnessey

Is artificial intelligence coming for your sales job? Not if you understand the power of business acumen, value selling, and strategic adoption of tools that amplify, not replace, human expertise. In this high-impact episode of Two Tall Guys Talking Sales, Kevin and Sean tackle the loud claims of AI-induced layoffs with a grounded, practical message for salespeople and sales managers: evolve or fall behind. This is not a doomsday episode; it’s a wake-up call, a roadmap, and a motivational boost for anyone in the world of revenue generation, sales processes, and messaging strategy.

Whether you’re a frontline salesperson or a VP of sales leading a team, this conversation will inspire you to rethink how you work, what skills future-proof your career, and how AI can become your competitive advantage instead of your competitor.

Key Topics Discussed

  • The 4 Irreplaceable Skills That Safeguard Sales Careers (01:00)
    Sean breaks down a framework for evaluating whether your job is AI-proof, hint: if you’re in B2B sales and good at it, you’re likely already building a durable edge.
  • How AI Mirrors the Arrival of the Internet in Sales Evolution (04:10)
    Kevin draws a compelling parallel between today’s AI landscape and the early days of the internet, showing why this shift is just as transformative.
  • Sales Management and Strategic Value in an AI World (02:46 & 07:31)
    From leadership and team building to messaging and workflow design, the episode highlights why sales managers need to think beyond quotas and towards long-term enablement.
  • A Personal Story of Old-School Sales and the Power of Adapting Tools (08:00)
    Sean shares a nostalgic (and relevant) story about his father’s sales career before personal computers, offering perspective on how sales adapts across generations.
  • Weaponizing Your Time: Using AI to Amplify Human Strengths (13:00)
    Kevin delivers a call to action on how to audit your own sales day and offload low-value tasks through automation, freeing up more time for high-impact strategy and consultation.

Key Quotes

  • “You won’t lose your job to AI, you’ll lose your job to a better salesperson who uses AI.”
    – Sean O’Shaughnessey (01:02)
  • “If you’re not using AI, or any sales technology, you’re not doing your job. You’re underperforming.”
    – Kevin Lawson (06:11)
  • “Sales worked before computers, and it will work after AI. What changes is how well you adapt the tools available.”
    – Sean O’Shaughnessey (10:04)
  • “Your time is your greatest asset, and your biggest liability, when you’re not using it to its highest utility.”
    – Kevin Lawson (14:00)

Additional Resources

  • Sean’s original blog post on this topic (available in the B2B Sales Lab and LinkedIn) https://newsales.expert/2025/06/b2b-sales-in-the-age-of-ai-why-top-salespeople-will-thrive-while-the-repetitive-roles-disappear/
  • B2B Sales Lab community discussion on sales evolution and AI https://b2b-sales-lab.com/
  • Tools mentioned: ChatGPT, Perplexity, Gemini (as starting points for AI integration)

A Significant Actionable Item from this Podcast

Audit your sales day for repeatable, low-value tasks that can be automated.
Pick one of them, like researching prospects, summarizing meeting notes, or drafting follow-ups, and replace it with an AI tool like ChatGPT or Perplexity. You’ll recover time, increase productivity, and move closer to building a modern, AI-augmented sales practice.

Final Summary

This episode of Two Tall Guys Talking Sales isn’t about fear, it’s about focus. Sales success today requires a sharp blend of strategic thinking, tool adoption, and human skills that are nearly impossible to replicate. Kevin and Sean lay out a blueprint that every sales leader, rep, and business owner should follow to thrive in this new era. If you’re serious about sales management, value selling, messaging clarity, and staying ahead of disruption, this episode will give you the mindset and tactical clarity to act now. Don’t just listen, level up.

Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

By Sean O'Shaughnessey

Sales isn’t about persuasion but service, resilience, and growth. In this episode of Two Tall Guys Talking Sales, co-hosts Kevin Lawson and Sean O’Shaughnessey welcome sales leader and former professional athlete Jeff Parris to explore the fundamental skills that separate elite salespeople from the rest. Drawing on decades of experience, Jeff shares three often-overlooked yet foundational competencies that drive sales success, and they’re not what you’d expect. Whether you’re a VP of Sales building a high-performance team or a seller looking to level up, this episode delivers sharp insights on value selling, business acumen, and sales management excellence.

Key Topics Discussed

  • Why great salespeople see themselves as servants first (approx. 04:00)
    Jeff outlines why a “motivation to serve” mindset creates stronger client relationships and more consistent revenue generation.
  • Ego Drive vs. Ego Trip: Understanding the will to win without arrogance (approx. 07:30)
    Learn how ego drive, a hunger to persuade for the buyer’s benefit, builds durable sales performance.
  • Curiosity as the gateway to sales mastery (approx. 10:15)
    Jeff and Sean dig into why curiosity fuels continuous improvement and business acumen across every sales process.
  • How to coach the “accidental salesperson” into a top performer (approx. 11:45)
    Kevin asks how people without formal sales backgrounds can thrive by developing the right mindset.
  • Sales leaders as talent architects: Building high-performance teams (approx. 02:00)
    Jeff draws on his athletic past to share what makes a sales team championship-worthy.

Key Quotes

  • “Sales isn’t something we do to people, it’s something we do for people.”
    — Jeff Parris (04:00)
  • “The real goal of a great salesperson is: ‘Mr. Prospect, let me help you solve that problem.”
    — Sean O’Shaughnessey (05:55)
  • “Having the right people, with the right skills, in the right seats makes winning so much easier.”
    — Kevin Lawson (03:36)
  • “Curiosity leads to better solutions. Every interaction is a chance to learn and improve your craft.”
    — Jeff Parris (10:50)

Additional Resources

A Significant Actionable Item from this Podcast

Evaluate your team (and yourself) on the “Service–Drive–Curiosity” Triad.
Start by asking three questions:

  1. Does this salesperson show a genuine desire to serve the customer’s goals?
  2. Do they take pride in persuading with purpose, not just for commission but impact?
  3. Are they consistently seeking to learn more about the customer, the industry, and their performance?

Use these questions in your next 1-on-1 or team coaching session to align your talent strategy with the kind of sales success that sustains revenue generation.

Why You Should Listen to This Episode

If you’re tired of surface-level sales advice, this conversation will challenge your thinking and expand your toolkit. Jeff Parris brings clarity, conviction, and humility to what it means to lead with purpose in today’s complex B2B landscape. From building elite sales teams to refining your individual sales strategy, this episode is packed with practical wisdom for leaders, sellers, and anyone serious about mastering the craft of sales. Tune in now and discover the underestimated traits that drive extraordinary outcomes.

Two Tall Guys Talking Sales – Mastering Sales Hiring with John Lee – Sales Management Insights for Growth-Focused Teams – Episode 138

Two Tall Guys Talking Sales – Mastering Sales Hiring with John Lee – Sales Management Insights for Growth-Focused Teams – Episode 138

By Sean O'Shaughnessey

In this week’s episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined by the “Elder Statesman” of fractional sales management: John Lee. With nearly four decades of experience and a deep track record of helping companies hire top-performing sales professionals, John shares a masterclass in sales hiring strategy. Whether you’re scaling from a two-person team to ten or trying to avoid costly hiring mistakes, this episode delivers practical, field-tested advice on building elite sales teams, strengthening your sales processes, and aligning talent with company culture.

Don’t miss this conversation if you’re committed to improving your sales success through smarter hiring, better business acumen, and scalable revenue generation.

Key Topics Discussed:

  • The Hiring Mindset for Growth Companies (00:01:45)
    Why hiring rock stars—not warm bodies—matters and how John filters for high performers.
  • From First Hire to Scaling a Team (00:04:44)
    CEOs and sales leaders must ask the evolving questions when hiring their 3rd, 5th, or 10th rep.
  • Psychographics, Not Just Resumes (00:05:24)
    How John builds candidate profiles that match top performers using behavior and motivation, not just skills.
  • Parallel Sales and Hiring Processes (00:08:00)
    Why a successful sales hiring process mirrors your value selling strategy—with defined steps, assessments, and clear messaging.
  • Avoiding Common Hiring Mistakes (00:11:43)
    The critical danger of hiring salespeople who are better at selling themselves than your solution.
  • Top 3 Rules for Hiring Sales Talent (00:13:33)
    John’s unfiltered checklist for hiring decisions that fuel revenue growth and protect your sales culture.

Key Quotes:

  • John Lee: “Don’t hire someone who can’t show they’ve been successful—and don’t hire someone who doesn’t fit your culture.” (00:13:57)
  • Sean O’Shaughnessey: “A salesperson might not be able to sell your product to save their life—but they’re often great at selling themselves. That’s a trap for business owners.” (00:11:55)
  • Kevin Lawson: “You talk about hiring the way you talk about sales infrastructure—it’s all about process, fit, and purpose.” (00:07:42)

Additional Resources Mentioned:

A Significant Actionable Item from this Podcast:

Design a Hiring Process Like a Sales Process
Treat your hiring efforts with the same rigor as your sales process. Start by defining a psychographic profile based on your top performers. Use structured assessments to evaluate “sales DNA” and focus interviews on demonstrated success, not just confidence. Then, make cultural fit a deal-breaker. Great hires aren’t just competent—they’re aligned with your mission, methods, and team dynamics.

Summary Paragraph:

This episode is essential listening for sales leaders and business owners looking to scale their teams without sacrificing culture, performance, or momentum. John Lee brings a rare mix of seasoned sales management expertise and real-world hiring acumen to the table. If you want to improve revenue generation through smarter hiring and better sales strategies, you’ll find actionable insights packed into every minute. Don’t settle for average; build a sales team that drives success. Tune in now.

Understanding Your Customers: The Role of Buyer Personas and Quarterly Business Reviews

Understanding Your Customers: The Role of Buyer Personas and Quarterly Business Reviews

By Sean O'Shaughnessey

Want to know the real secret behind successful sales? It’s not just about knowing what your customers need. The true power lies in understanding who they are at their core.

Have you ever wondered why some sales professionals consistently outperform their peers? The answer often comes down to their mastery of buyer personas and detailed profiles that capture the essence of your ideal customers.

Think of buyer personas as your secret weapon in the sales battlefield. These aren’t just random customer profiles thrown together in a rushed afternoon meeting. They represent carefully crafted composites of your most valuable clients, built from real-world data and insights. Your company might need several of these personas, each targeting different market segments with laser precision.

Creating effective buyer personas demands more than just surface-level observation. Start with a thorough analysis of your business landscape. Examine your strengths and weaknesses. Map out the opportunities that excite you and the threats that keep you up at night. This foundation helps you understand exactly where you fit in your customers’ world.

What makes your top customers tick? The answer lies in meaningful conversations with your best clients. These discussions should dig deep into both quantitative and qualitative factors. Demographics tell part of the story – age, position, education, family status. But the real gold comes from understanding their motivations. Why did they choose you? What problems do you solve that keep them coming back?

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Turning Competition into Opportunity: A Guide for Success in Sales

Turning Competition into Opportunity: A Guide for Success in Sales

By Sean O'Shaughnessey

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

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

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

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

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

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