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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Two Tall Guys Talking Sales – How Sales Leaders Use CRMs to Align Sales Processes, Value Selling, and Revenue Management – Episode 152

Two Tall Guys Talking Sales – How Sales Leaders Use CRMs to Align Sales Processes, Value Selling, and Revenue Management – Episode 152

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey build on last week’s discussion of qualification methodologies and take the conversation further—into how these frameworks should live inside your CRM. From aligning sales processes with the buyer’s journey to enforcing accountability at each stage, this conversation offers practical strategies that every sales leader and salesperson can implement. Expect a deep dive into sales management, revenue generation, sales processes, and how value selling thrives when marketing and sales teams work in sync.

Key Topics Discussed

  • Why your CRM is the right home for qualification methodologies (00:48)
  • Best practices for embedding qualification questions into sales processes (02:01)
  • How sales leaders enforce discipline and consistency across teams (03:18)
  • Eliminating Excel spreadsheets and consolidating data for effective revenue management (05:12)
  • Aligning marketing collateral with sales strategies to support qualification and value selling (06:00)
  • Real-world stories of late-stage deal failures caused by missing buyer-side approvals (10:21)

Key Quotes

  • Kevin Lawson (05:12): “Oh, please, oh, please evacuate Excel spreadsheets from your solution guide… For the purposes of this discussion, we want to strenuously avoid having third-party apps disconnected from your system.”
  • Sean O’Shaughnessey (10:40): “There is nothing worse than missing your quarterly number because you didn’t know how they were going to buy… Knowing the paperwork process is the difference between celebrating the win and missing your commission check.”
  • Kevin Lawson (14:10): “Having a qualification methodology mapped into your CRM, aligned with a buyer’s journey and supported by marketing resources, gives you a fully wrapped system that prevents that dreaded CEO call asking, ‘What’s the status of that deal?’”

Additional Resources

A Significant Actionable Item from this Podcast

Embed your qualification methodology directly into your CRM, tied to each stage of your sales process.

Don’t let critical deal information reside inside spreadsheets or Word docs; configure your CRM so progression requires those qualification questions to be answered. This not only improves sales accuracy but also enhances revenue management, ensures consistency across your team, and creates alignment with marketing resources to drive value selling.

Summary

This episode of Two Tall Guys Talking Sales is a must-listen for anyone serious about building sustainable sales success. Sean and Kevin reveal how sales strategies such as qualification methodologies come to life when fully integrated into CRM-driven sales processes. You’ll learn why sales management must prioritize data consistency, how business acumen prevents late-stage deal disasters, and how aligning messaging between sales and marketing fuels stronger revenue generation. If you want practical insights on improving your sales processes and elevating your organization’s performance, download this episode today and start putting these best practices to work.

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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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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From Reporting to Coaching: Elevate Your One-on-One Sales Meetings to Drive Performance and Trust

From Reporting to Coaching: Elevate Your One-on-One Sales Meetings to Drive Performance and Trust

By Sean O'Shaughnessey

A one-on-one sales meeting is not a reporting meeting. It’s not about reviewing what already happened. And it’s definitely not about the manager doing most of the talking. The purpose of a one-on-one pipeline review is to develop the salesperson, surface challenges, and accelerate opportunities. If your one-on-ones are anything less, you’re leaving performance on the table.

Sales leaders often default to micromanagement. 

Especially when the rep is new or struggling. But that approach backfires. It creates dependency and stifles problem-solving. The goal is to coach your reps into leading the meeting. That shift changes everything. When reps own the agenda and bring forward deal-level insights, they’re forced to think critically. That’s where growth happens.

If you’re leading a sales team or are a CEO playing the role of sales manager, you need to establish a clear structure. But the rep does the prep. You define the meeting cadence and format. Weekly or bi-weekly, depending on your velocity. You outline the sections: committed deals, stalled deals, and at-risk deals. 

But the rep fills in the content. They come to the meeting ready to walk you through each opportunity, with specific updates and clear asks.

Preparation is non-negotiable. For both sides. 

The salesperson should have updated their CRM before the meeting. The manager should have reviewed that data in advance. If either party shows up unprepared, the meeting becomes reactive. 

A waste of time. And it erodes trust quickly. 

Reps notice when you haven’t read the notes. They know when you’re winging it. And if they feel their effort isn’t valued, they’ll stop putting in the effort.

You want to create a culture where preparation is expected and rewarded. 

The fastest way to management failure is to ask questions that could have been answered by reading the CRM. Instead, use that time: 

  • To probe deeper. 
  • Ask about the deal strategy. 
  • Challenge assumptions. 
  • Help salespeople spot gaps they missed. 

That’s where your experience has real value.

It’s tempting to jump in and solve the problem. Especially when you see the red flags before the rep does. But resist the urge. Let them talk it through. Coach them toward the insight. Your job isn’t to close the deal; it’s to build someone who can. That means teaching them how to identify weak spots, how to pressure test a deal, and how to re-engage a stalled buyer. The real value of one-on-ones is in that development.

Think about how you coach. 

Are you diagnosing for them? Or are you helping them diagnose for themselves? When a rep says “this deal is solid, no issues,” that’s a red flag. Every deal has risk. Your job is to help them uncover it. Ask: “What’s the biggest thing that could derail this?” Or “What’s the last thing the buyer said that gave you pause?” These questions surface the truth. And they teach reps to self-assess more effectively.

There’s a fine line between coaching and grading. You want reps to be honest about their pipeline without fear of judgment. 

If a deal is weak, that’s not a character flaw. It’s a coaching moment. 

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Two Tall Guys Talking Sales – Winning Sales Strategies for Productive, High-Impact Pipeline Reviews – Episode 149

Two Tall Guys Talking Sales – Winning Sales Strategies for Productive, High-Impact Pipeline Reviews – Episode 149

By Sean O'Shaughnessey

Pipeline reviews don’t need to feel like an ambush. In this episode, Kevin Lawson and Sean O’Shaughnessey break down how to turn pipeline meetings into high-value working sessions that improve sales management, strengthen sales processes, and accelerate revenue generation. The conversation focuses on preparation discipline, trust, and transparency, as well as a practical playbook for advancing complex deals through relationship mapping and peer-to-peer executive engagement.

You’ll hear straightforward sales strategies you can implement immediately, whether you lead a large enterprise team or a small, founder-led organization. Expect a sharp focus on business acumen, value selling, and the day-to-day messaging that keeps deals moving. The result is a meeting format that fuels sales success and better revenue management, not another hour of defensive status reporting.

Key Topics Discussed

  • Make pipeline reviews not suck — Focus the agenda on the few deals that genuinely need help; skip deep dives on healthy opportunities. [~00:00:00]
  • The salesperson’s prep checklist — Current notes, clear qualification status, and a concrete next step; never open with “I need to get a meeting.” [~00:03:00]
  • Trust, transparency, and speed — Why open admission of gaps prevents executive “gotchas” and keeps the team collaborative. [~00:04:34–00:05:34]
  • Taming the “big deal” distraction — How sales leaders manage CEO attention and ensure one opportunity doesn’t hijack the meeting. [~00:07:52–00:08:20]
  • Relationship mapping for top deals — Title-to-title engagement, executive assignments, and the “11-on-11” football metaphor for flawless execution. [~00:09:00–00:11:55]
  • Adapting for smaller orgs — Three-on-three analogy, “weaponize” your internal team as peer resources, and coach reps to lead 1:1s. [~00:12:30–00:15:06]

Key Quotes

  • Sean O’Shaughnessey [~00:01:36]: “Bring up the ones that hurt, the deals where you need help. Wouldn’t it be nice to get helped in a pipeline review instead of just being told to ‘get your ass out there and go work on it’?”
  • Kevin Lawson [~00:05:00]: “Transparency is our key that will keep us moving forward and fast. Sales pipeline meetings don’t have to be the Spanish Inquisition.”
  • Sean O’Shaughnessey [~00:11:34]: “Run your top deals like you’re running a football team, every player knows their assignment, and you execute flawlessly.”
  • Kevin Lawson [~00:14:33]: “For one-to-ones, the salesperson should be leading the meeting, your job is to coach them to bring challenges you can clear.”

Additional Resources (mentioned in the episode)

  • Sales Meeting Agenda Templates — Free downloadable agendas for effective pipeline reviews and 1:1s (from Sean and Kevin’s sites).
  • B2B Sales Lab Community — A peer-led forum to refine sales strategies, strengthen messaging, and accelerate revenue generation. https://b2b-sales-lab.com/

A Significant Actionable Item from this Podcast

Adopt the “Help-First Pipeline Review” and Relationship Map.

Before your next review, split your pipeline into two lists: On-Track and Needs Help. Use meeting time almost exclusively on the “Needs Help” list. For each flagged deal, arrive with: (1) current status and qualification level, (2) the single next step, and (3) a relationship map that pairs your execs and functional leaders title-to-title with the customer’s counterparts (CEO↔CEO, CFO↔CFO, VP Eng↔VP Eng). Assign those internal players specific outreach tasks and deadlines. This simple shift transforms pipeline reviews into working sessions that improve sales management, sharpen sales processes, and advance value-based conversations, fast.

Two quick tips to lock it in:

  1. Never start with “I need to get a meeting.” Instead, say, “I’m trying to reach Larry; here are the three touches I’ve already made and my next move.”
  2. Preempt “big deal” derailments by updating its status in CRM ahead of time and summarizing it briefly; then return to the prepared “Needs Help” list.

Summary

If pipeline reviews feel like public performance reviews, this conversation will reset the culture. Kevin and Sean outline a decisive, repeatable approach that blends business acumen, crisp messaging, and practical value selling to move deals. By prioritizing help over inspection, mapping peer-to-peer relationships, and coaching reps to lead, you’ll turn a dreaded ritual into a lever for sales success and consistent revenue management. Queue it up, your next pipeline meeting can actually be the best hour of your sales week.

Two Tall Guys Talking Sales – Chris Spanier Explains Marketing Professional Services: Sales Strategies That Actually Work – Episode 142

Two Tall Guys Talking Sales – Chris Spanier Explains Marketing Professional Services: Sales Strategies That Actually Work – Episode 142

By Sean O'Shaughnessey

When marketing professional services, the playbook isn’t the same as product sales, and today’s episode dives into exactly why. Sean O’Shaughnessey and Kevin Lawson are joined by returning guest Chris Spanier, CEO of Carpe Diem Consulting Group and host of the Practical Actionable Marketing podcast. This conversation tackles the nuances of sales strategies for service-based businesses, blending value selling with measurable marketing and aligning both functions for stronger revenue generation. If you’re a business owner, consultant, or fractional executive trying to sharpen your sales processes and improve messaging, this episode is a goldmine of practical advice.

🔑 Key Topics Discussed

  • [02:44] Why traditional product marketing doesn’t work for professional services—and how to adapt
  • [03:46] The importance of measuring marketing effectiveness and integrating KPIs into the sales process
  • [07:36] How to position and market services that don’t have tangible “speeds and feeds”
  • [08:28] Letting go of the fear of “giving away your secret sauce” in thought leadership content
  • [10:30] Systemizing stories and messaging to scale sales efforts across a growing team
  • [12:14] How to use lead nurturing email campaigns to drive engagement and trust over time

🗣️ Key Quotes

  • Sean O’Shaughnessey:
    “Sales is a really expensive marketing arm if you’re not doing really good marketing.”
    — [05:59]
  • Kevin Lawson:
    “Tell how you win, how you help others win, and how they win when working with you—this is as key as anything in professional services.”
    — [10:52]
  • Chris Spanier:
    “If you freely share value, people won’t take advantage of you—they’ll start trusting you. That’s the first step in real sales success.”
    — [08:54]
    “Marketing is half magic and half numbers. But the numbers—that’s where the proof comes in.”
    — [04:14]

📚 Additional Resources

✅ A Significant Actionable Item from this Podcast

Systemize your lead nurturing.
Create a recurring, value-focused email campaign to maintain top-of-mind awareness. Whether your cadence is every three or six weeks, focus 80% on providing helpful insights and only 20% on pitching your services. Tracking measures email open rates and clicks, and then the behavior is aligned with site visits or follow-up outreach. This strategy turns occasional touchpoints into consistent momentum, critical for long-cycle sales in professional services.

🎧 Why You Should Listen Now

This episode is packed with strategic clarity and tactical insight for anyone selling invisible services. Whether you’re a fractional executive, consultant, or marketing-savvy sales leader, you’ll leave with a more innovative approach to messaging, a stronger understanding of sales and marketing alignment, and actionable ways to drive revenue generation with business acumen. Tune in now and rethink how you build trust and momentum in your professional services pipeline.