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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AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

By Sean O'Shaughnessey

AI isn’t replacing salespeople, it’s making them more effective. The real risk isn’t losing your job to AI; it’s losing to a competitor who uses AI better than you do. Sales professionals who integrate AI into their workflow will outperform those who don’t. 

It’s not about technology taking over but about using technology to gain an edge. The market is becoming increasingly competitive, and the most efficient salespeople will emerge victorious.

Time is a salesperson’s most valuable asset. 

Every minute spent on administrative tasks is a minute not spent selling. AI helps reclaim those lost hours. Tools that automate writing, scheduling, and research allow salespeople to focus on what matters: building relationships and closing deals. If you’re not leveraging AI to increase productivity, you’re leaving opportunities on the table.

Sales emails need to be clear and professional. AI-powered writing assistants ensure your messages are polished and effective. A poorly written email can cost you a deal. AI tools catch grammatical mistakes, improve clarity, and even suggest more effective phrasing. This isn’t just about looking professional; it’s about being understood. 

If your message isn’t clear, it won’t convert.

Presentations are another time-consuming task. AI can generate professional decks in minutes. Instead of spending hours designing slides, salespeople can focus on developing effective strategies. AI-powered tools create branded, structured presentations based on simple inputs. This ensures consistency while saving time. Sales professionals who utilize AI for presentations can focus on delivering insights rather than formatting slides.

CRM systems are the backbone of sales operations. AI enhances CRM by automating data entry, tracking customer interactions, and suggesting next steps. Salespeople often struggle with keeping CRM data updated. AI reduces this friction by automatically capturing and organizing information. A well-maintained CRM leads to better forecasting and stronger customer relationships. 

If your CRM doesn’t have AI capabilities, it’s time to upgrade.

AI-driven insights enable sales managers to make more informed decisions, rather than relying on instinct. Managers can use AI to analyze performance trends, identify coaching opportunities, and predict revenue outcomes. AI doesn’t replace leadership; it enhances it. 

Sales managers who adopt AI can build stronger teams and achieve better results. Ignoring AI in sales management is a strategic mistake.

Lead generation is another area where AI adds value. AI-powered tools can analyze vast amounts of data to identify high-potential prospects. Instead of spending hours researching leads, salespeople can receive AI-generated recommendations. This allows for more targeted outreach and higher conversion rates. AI doesn’t just find leads, it finds the right leads.

Sales follow-up is often inconsistent. AI ensures follow-ups happen at the right time with the right message. Automated reminders and AI-generated responses keep deals moving forward. 

A well-timed follow-up can be the difference between closing a deal and losing it. AI helps salespeople stay on top of their pipeline without relying on memory.

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Turning Around Sales Performance: Strategies for CEOs and Sales Managers to Foster Internal Alignment

Turning Around Sales Performance: Strategies for CEOs and Sales Managers to Foster Internal Alignment

By Sean O'Shaughnessey

Navigating a sales turnaround isn’t just about fixing numbers; it’s about transforming the business. It’s about realigning expectations, rebuilding internal trust, and creating a structured, sustainable path forward. 

If you’re a CEO, sales manager, or a key salesperson in your organization, the pressure to reverse a sales slump can feel overwhelming. However, the truth is that turnarounds aren’t made in a sprint; they’re built through clarity, consistency, and effective communication.

Too often, sales leaders make the mistake of focusing only on the downward trend. They get caught up in the urgency of the numbers and forget that the real challenge lies in managing upward, setting expectations with executive leadership, and aligning them with reality. 

If your sales team is underperforming, your internal stakeholders are your new audience. Just as with external prospects, you need to manage their expectations with a clear, actionable plan.

The process starts with a shift in mindset. 

Instead of viewing upper management as critics, think of them as clients. What do they need to believe in this turnaround? What information do they need to trust your leadership? Start by building a high-level outline. Avoid over-engineering the details in the early stages. Focus on where you want to go, then reverse-engineer the steps to get there.

Every turnaround starts from a rear position. That means your first job is to stop the downward momentum. Before you can scale revenue, you need to stabilize it. That requires a clear definition of success, agreed upon by everyone involved. 

  • Are you trying to double revenue in 12 months? 
  • Or just return to last year’s baseline? 
  • Is that goal realistic given your market, team, and resources? 

If not, revise it. A stretch goal is fine. A fantasy is not.

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Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey dive deep into one of the most misunderstood dynamics in business: the relationship between sales and marketing. Pulled directly from a thought-provoking question inside the B2B Sales Lab community, this conversation explores how sales teams can contribute meaningfully to marketing efforts and why that collaboration drives better revenue generation. Whether you lead a sales team, run marketing campaigns, or wear both hats in a small business, this episode gives you practical strategies to align your teams, sharpen your messaging, and enhance sales success.

Key Topics Discussed

  • The Role of Sales in Marketing & Content Development (00:00)
    How sales leaders can become strategic contributors to content and campaign direction.
  • Being the Voice of the Customer Across the Business (00:02)
    Why sales must act as a conduit of market intelligence, not just for marketing but across production, delivery, and operations.
  • Sales Behavior That Builds or Breaks Internal Trust (00:04)
    The importance of accountability and humility when offering feedback to other departments.
  • Making Marketing a Regular Part of Sales Meetings (00:08)
    A tactical breakdown of how to engage marketing in the sales rhythm without derailing productivity.
  • Field Collaboration: Invite Your Internal Teams to Ride Along (00:10)
    Why taking engineers or operations managers on customer calls creates stronger cross-functional empathy and better customer experiences.
  • Marketing Assets: Create Them, Use Them, Give Feedback (00:12)
    How to close the feedback loop on content effectiveness and ensure sales uses what marketing builds.

Key Quotes

  • “Sales is accountable for driving the revenue, but sales is also accountable for working with marketing to get to a market-facing message that addresses current needs.”
    — Kevin Lawson (00:00)
  • “Your job in sales is to be the best-run department in the company. If you’re not, your opinion probably doesn’t matter.”
    — Sean O’Shaughnessey (00:08)
  • “Please, oh please, use the tools your marketing team creates for you. If you don’t, that’s on you.”
    — Kevin Lawson (00:12)
  • “There’s no better way to get internal teams aligned with customers than to take them on sales calls. Let them breathe your air and eat at Burger King between meetings.”
    — Sean O’Shaughnessey (00:11)

Additional Resources

  • B2B Sales Lab Community: A peer group for sales professionals focused on sharpening sales processes, messaging, and revenue management. www.b2b-sales-lab.com

A Significant Actionable Item from this Podcast

Hold a joint sales-marketing meeting each quarter.

Schedule a dedicated 30-minute session within your sales team’s recurring meeting where your marketing counterpart joins to review current messaging, upcoming campaigns, and voice-of-the-customer insights. Let marketing ask questions, present new content, and gather sales feedback. Use this as a structured loop to align both teams on business acumen, sales strategies, and revenue goals.

Why You Should Listen Now

If you’ve ever wondered why your sales messaging isn’t landing or why marketing feels “out of touch,” this episode is for you. Kevin and Sean pull back the curtain on how high-performing sales organizations dissolve silos, share real-time customer feedback, and co-create assets that drive revenue. Whether you’re a VP of Sales, a marketing leader, or a business owner trying to scale effectively, you’ll walk away with ideas you can implement this week to align your teams for better revenue generation and sales success. Tune in now and start building the team your customers deserve.

Two Tall Guys Talking Sales – Patrick O’Donnell Explains How to Hire and Onboard Sales Talent That Actually Performs – Episode 139

Two Tall Guys Talking Sales – Patrick O’Donnell Explains How to Hire and Onboard Sales Talent That Actually Performs – Episode 139

By Sean O'Shaughnessey

In this high-impact episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome sales acceleration expert Patrick O’Donnell to tackle one of the toughest challenges facing small business CEOs: hiring and onboarding top-performing sales talent. Together, they dive deep into proven sales strategies that help CEOs find strong candidates and keep them engaged, successful, and driving revenue. If you’ve ever hired a salesperson who didn’t work out, or you’re planning to hire your first, this conversation is your roadmap to sales success. From creating a robust onboarding plan to integrating soft skills training and cultural alignment, this episode is packed with value-selling insights you can apply immediately.

Key Topics Discussed:

  • [00:01:00] Why small business CEOs struggle to attract and retain top salespeople
  • [00:03:00] Patrick’s proven hiring and onboarding process for sales roles
  • [00:05:10] The importance of structured 30-60-90 day plans and Sean’s GUTS framework
  • [00:07:00] Kevin’s NASA Plan for onboarding: A granular, hourly approach to early success
  • [00:10:00] The role of soft skills and professional development in retaining talent
  • [00:11:50] A lighthearted look at entrepreneurship: Why Patrick bought a historic Indianapolis tavern

Key Quotes:

  • “They’re in such a hurry to take the sales hat off their head that they hire the first person who looks okay on the surface. That rushed approach almost always ends poorly.”
    – Patrick O’Donnell [00:02:06]
  • “I hand every new rep a GUTS document—Getting Up To Speed. It’s a 30-60-90 plan that clearly spells out what they need to accomplish. They can be ahead, but they can’t fall behind.”
    – Sean O’Shaughnessey [00:05:10]
  • “Most small business owners think they have a plan because it’s in their head. But if it’s not written down, it doesn’t exist.”
    – Kevin Lawson [00:07:29]
  • “We want every new hire to be the most professional person in the company, because it’s their job to make everyone around them better.”
    – Sean O’Shaughnessey [00:10:35]

Additional Resources:

  • LinkedIn profile for Patrick O’Donnell https://www.linkedin.com/in/patrickwodonnell/
  • Soft skills training programs referenced by Sean for onboarding enrichment
  • GUTS (Getting Up To Speed) framework and NASA Plan discussed during onboarding best practices

A Significant Actionable Item from this Podcast:

Implement a Written 30-60-90 Onboarding Plan with a Two-Week NASA Schedule.
Salespeople need clarity to succeed. Whether you’re a first-time sales manager or a seasoned executive, stop relying on verbal plans or “tribal knowledge.” Create a written 30-60-90 onboarding plan that details expectations, milestones, and key outcomes. For the first two weeks, apply the NASA method: a daily, hour-by-hour schedule that aligns the new hire with every department, cultural cue, and technical requirement. Doing so sets a strong foundation for success and dramatically reduces early turnover.

Summary Paragraph:

If you’re serious about improving your sales management, elevating your sales processes, and building a team that drives real revenue generation, this episode of Two Tall Guys Talking Sales is essential listening. Kevin, Sean, and Patrick break down what too many business owners get wrong—and how you can get it right. Whether you’re scaling a team or hiring your first rep, these insights around onboarding, messaging, and business acumen will accelerate your journey toward consistent sales success. Press play now and walk away with tools you can use today.

Validation Events: The Unsung Hero of Sales Process Discipline

Validation Events: The Unsung Hero of Sales Process Discipline

By Sean O'Shaughnessey

In the complex world of B2B selling, trust is built in stages. The challenge in all sales campaigns is ensuring the prospect trusts they are making the best decision for their business.

  1. Do they trust that the salesperson is giving them all of the information?
  2. Do they trust that the company will support them after the sale?
  3. Do they trust that the product will perform as they expect it to perform?

As I have explained in my book, Eliminate Your Competition, as well as the blog for that book and in this blog, the prospect needs to trust all three elements the salesperson is selling:

  1. They need to trust the product.
  2. They need to trust the company behind the product.
  3. They need to trust the salesperson.

Prospects listen to your sales message, review your materials, and hear your claims, but none of that guarantees belief or trust. Trust is validated when your claims are validated. That’s why validation events are crucial to any rigorous sales process.

In The Qualified Sales Leader, John McMahon stresses the importance of customer-driven validation. He cautions sales leaders against relying on internal optimism or anecdotal “good signals” from prospects. Instead, McMahon emphasizes observable proof—real buyer behavior that confirms alignment, commitment, and value. Validation events are when the customer takes action to validate that what you’ve promised is accurate and valuable.

An excellent sample sale process flow looks like this:

  1. Discover
  2. Scoping
  3. Economic Buyer Meeting
  4. Validation Event
  5. Business Case and Final Proposal
  6. Negotiate and Close

As you can see, the Validation Event is the last step before creating the final business case, which will be bundled with your final proposal.

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Two Tall Guys Talking Sales – Scaling Smarter: Building Sales Teams with Steve Caton – Episode 136

Two Tall Guys Talking Sales – Scaling Smarter: Building Sales Teams with Steve Caton – Episode 136

By Sean O'Shaughnessey

What does it take to scale a sales organization in today’s unpredictable business environment? In this dynamic episode of Two Tall Guys Talking Sales, hosts Sean O’Shaughnessey and Kevin Lawson welcome back Steve Caton, CEO of Altezza Solutions, to unpack the nuances of scaling sales teams, especially through the power of fractional sales professionals. Together, they explore the critical role that sales processes, sales management, and business acumen play in enabling organizations to grow without overspending or compromising performance. Whether you’re navigating the “zero to one” phase or planning your expansion from one rep to five, this episode offers a roadmap for smart, sustainable revenue generation.

Key Topics Discussed

  • Zero to One vs. One to One Hundred: Two Models for Scaling Sales Teams (00:01:14)
    Kevin and Steve outline the difference between launching your first rep and accelerating team expansion, with a focus on structured growth.
  • Fractional Salespeople as a Low-Risk Growth Strategy (00:02:45)
    Steve explains how the fractional model supports learning, experimentation, and ROI without overcommitting resources too early.
  • Determining the Right Time to Expand Territories or Add Headcount (00:04:10)
    The team discusses key signals—like activity level, lead flow, and deal volume—that indicate when it’s time to grow.
  • Using Leading Indicators vs. Lagging Indicators in Sales Management (00:06:16)
    Steve shares the importance of measuring inputs (calls, meetings, proposals) over outputs (closed deals) to ensure predictable scale.
  • The Power of Process-Driven Selling for Sales Success (00:13:08)
    Sean and Steve emphasize why experienced sales pros rely on systems, not improvisation, and why process must precede people.

Key Quotes

  • Kevin Lawson (00:01:34):
    “Think hockey stick versus gradual—zero to one is about getting that first good hire. That’s when you unlock real scale potential.”
  • Steve Caton (00:02:45):
    “Start small, see what works, then expand. That’s the foundation of scalable revenue—and the fractional model makes that possible without spending a crazy amount of money.”
  • Sean O’Shaughnessey (00:08:00):
    “Sales is about finding the customer that is going to buy—that’s not just a marketing thing, that’s a sales thing.”
  • Steve Caton (00:13:08):
    “Process comes before people. If there’s no process, your reps will build one—and that distracts them from actually selling.”

Additional Resources

A Significant Actionable Item from this Podcast

Use leading indicators—not just closed deals—to decide when it’s time to grow your sales team. Many companies scale reactively, hiring after success arrives. But Steve Caton challenges leaders to evaluate the activity level of their reps—calls made, meetings scheduled, deals created—to make data-driven decisions before hitting a bottleneck. If your top performer is maxing out their productive hours, it’s time to split territories, not overload. Review your leading indicators this week and see where your next growth step should begin.

Why You Should Listen

This episode is a must-listen for founders, CEOs, and sales leaders trying to build smarter, not just bigger. With deep insight into the value of fractional sales professionals, the importance of sales strategies, and how to use data for effective revenue management, Steve Caton offers a practical, grounded view of what scalable sales success looks like. If you’re serious about growing your team without growing your headaches, hit play and take notes.

Two Tall Guys Talking Sales – Winning Without Discounting: Mastering Value Selling at Premium Prices – Episode 135

Two Tall Guys Talking Sales – Winning Without Discounting: Mastering Value Selling at Premium Prices – Episode 135

By Sean O'Shaughnessey

When it comes to holding firm on pricing, many salespeople stumble at the finish line, undermining their value and margin in pursuit of a quick win. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey explore the essential topic of value selling, especially when offering a premium-priced solution. They break down how business acumen, sales strategy, and relationship-based selling contribute to sales success—and how to confidently command the price your product deserves. If you’ve ever been told you’re “too expensive,” this is your playbook for holding the line and still closing the deal.

Key Topics Discussed

  • Why customers buy more than just your product—they buy your company and you (00:01:00)
  • The danger of sending a quote without a conversation (00:02:21)
  • How sales reps can create momentum in late-stage deals by previewing terms early (00:03:00)
  • Breaking away from “feeds and speeds” and focusing on business outcomes (00:05:00)
  • Real-world coaching example: winning a deal despite being $9,000 more expensive (00:08:25)
  • The importance of sales process alignment with customer learning styles (00:10:48)

Key Quotes

“Your customers are not just buying your product—they’re buying your company, and they’re buying the wisdom of the salesperson.”
— Sean O’Shaughnessey (00:01:00)

“Don’t just throw a document on their desk that says, ‘here’s my price.’ That’s not value selling. That’s transactional noise.”
— Kevin Lawson (00:03:21)

“I told her: thank them for the feedback. Tell them you can’t meet the price because you’re delivering something of higher value—and she won the deal.”
— Sean O’Shaughnessey (00:09:01)

“If you’re always responding with a discount, you’re not putting forward the confidence that your product actually delivers value.”
— Kevin Lawson (00:10:28)

A Significant Actionable Item from this Podcast

Stop emailing quotes—start previewing them. Before sending out another proposal or quote, schedule a call or meeting with your prospect to review the terms and value proposition. Use that time to reinforce the business impact of your solution and clarify any remaining concerns. This approach increases close rates and reduces last-minute pricing objections, protecting revenue and margin.

Summary

In today’s ultra-competitive B2B environment, salespeople must do more than deliver specs—they must deliver confidence. This episode of Two Tall Guys Talking Sales arms you with a clear, repeatable strategy for commanding premium pricing through value selling. If you’re serious about improving your sales management, sales processes, and revenue generation tactics, then this 15-minute episode could be the most profitable quarter-hour of your week. Tune in now and elevate your ability to win—without discounting.