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

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

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

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

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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B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

  1. Hard-to-automate skills
  2. Deployment-related skills
  3. Scarce, high-utility skills
  4. Skills hard for others to learn or replicate

Each of these aligns tightly with the demands of modern B2B sales.

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Two Tall Guys Talking Sales – Elevate Your Sales Game with B2B Sales Lab: A New Resource for Revenue Growth – Episode 141

Two Tall Guys Talking Sales – Elevate Your Sales Game with B2B Sales Lab: A New Resource for Revenue Growth – Episode 141

When sales professionals hit a roadblock, where do they turn? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey unveil an exciting new initiative: B2B Sales Lab, a private peer networking community designed to support salespeople, sales managers, and business owners in their journey toward revenue generation excellence. This isn’t just a conversation; rather, we are offering an invitation to join something powerful. If you’ve ever felt alone in a tough sales challenge or wished for experienced advice on your messaging, sales processes, or strategy, this episode is for you.

Key Topics Discussed

  • (00:00) Why selling isn’t easy and how sales professionals can benefit from a support network
  • (00:39) The creation and mission of the B2B Sales Lab community
  • (01:42) How the platform fosters peer-to-peer learning without judgment or pressure
  • (02:58) The importance of community in developing strong sales strategies and business acumen
  • (03:54) Guardrails that make this space safer and more effective than LinkedIn or Facebook groups
  • (05:00) Why there’s a membership fee—and why the first three months are free

Key Quotes

  • Sean O’Shaughnessey (00:01:00): “We’re creating a community where people can get together, bounce ideas off each other without fear—just designed to help.”
  • Kevin Lawson (00:02:58): “It’s unreasonable to think your small sales team has all the answers. But it’s completely reasonable to find a community that does.”
  • Sean O’Shaughnessey (00:04:16): “If you’re not a salesperson or sales leader, you’re not getting in. This isn’t about selling to each other. It’s about growing together.”

Additional Resources

  • B2B Sales Lab Information & Registration: https://newsales.expert/b2b-sales-lab
    (Free for the first three months with no obligation.)

A Significant Actionable Item from this Podcast

Join the B2B Sales Lab.
If you’ve ever wished you had a sounding board for a tough sales call, a creative partner to work through messaging, or a peer to validate your sales strategy, this is your moment. Visit the link in the show notes and apply to join the B2B Sales Lab. The first three months are free, giving you access to experienced sales minds, curated content on value selling and revenue management, and a judgment-free environment to grow your sales acumen. Don’t wait for your next deal to fall through; build your support system today.

Why You Should Listen

This episode is a call to action for sales professionals serious about growth. If you’re navigating complex sales cycles, seeking stronger messaging, or simply want a community that understands your world, the B2B Sales Lab might be the resource you’ve been missing. Kevin and Sean, both seasoned in sales leadership and sales management, offer not just insights but an entire framework to elevate your career. Listen now to learn how to take the next step toward sustainable sales success—and connect with others on the same journey.

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

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

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?

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

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

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

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

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

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

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

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

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

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

Key Topics Discussed

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

Key Quotes

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

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

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

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

A Significant Actionable Item from this Podcast

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

Episode Summary

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

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

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

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

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome business intermediary Tom Gottlieb of Berkshire Hathaway. Tom brings decades of experience in buying, selling, and valuing businesses across the Midwest. The conversation dives deep into what truly drives the value of a company—and how sales leaders and business owners alike can prepare their organizations for a future transition. Whether you’re a business owner considering a sale or a sales executive interested in how sales performance impacts company valuation, this episode delivers invaluable guidance. It’s part education, part strategy session, and all high-value insight.

Key Topics Discussed

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

Key Quotes

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

Additional Resources

A Significant Actionable Item from this Podcast

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

Why You Should Listen to This Episode

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

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

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

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

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

Key Topics Discussed:

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

Key Quotes:

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

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

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

Additional Resources:

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

A Significant Actionable Item from this Podcast:

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

Why You Should Listen to This Episode

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

Unlocking Sales Success: The Power of KPIs in Sales Processes

Unlocking Sales Success: The Power of KPIs in Sales Processes

Are your sales KPIs helping your team succeed? Many sales leaders focus solely on closed deals. This narrow view misses crucial elements of sustainable sales growth.

The journey matters more than the destination. Sales excellence follows a similar path. Your team’s daily actions and behaviors create the foundation for lasting success.

Effective sales measurement requires a comprehensive view of your team’s activities. Top performers consistently execute vital behaviors that drive results. They prospect strategically, nurture relationships, and expand their presence within existing accounts. These leading indicators paint a clearer picture of future performance than lagging metrics alone.

Your KPI framework must evolve beyond historical analysis. Forward-looking metrics help you spot opportunities and challenges before they impact revenue. What’s happening in your pipeline right now? How are your teams finding new prospects? Which accounts show growth potential?

Experience levels significantly impact appropriate performance measures. New salespeople face different challenges than seasoned veterans. A rookie might need help with fundamental sales behaviors while learning your company’s approach. They need clear operational guidance and structured metrics that reinforce proper execution.

Veteran salespeople bring established skills and proven track records. Their KPIs should emphasize continuous improvement and cultural alignment. How are they advancing their capabilities? What value do they add to the broader sales organization?

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