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.

From Manual to Automated: A Sales Pro’s Guide to Zapier, Make.com, n8n, and Pipedream

From Manual to Automated: A Sales Pro’s Guide to Zapier, Make.com, n8n, and Pipedream

By Sean O'Shaughnessey

A sales manager recently told me something that stuck: “We went from twenty hours per week of manual work to two hours. Our lead response time dropped from four hours to four minutes.” That dramatic transformation wasn’t magic—it was automation.

The reality is that sales teams today have more automation tools available than ever before. But with options like Zapier, Make.com, n8n, and Pipedream, the real challenge isn’t whether you should automate—it’s choosing the right platform for your team. Each one comes with strengths, limitations, and unique philosophies. Get that choice wrong, and you’ll waste time, money, and buy-in. Get it right, and you’ll see efficiency gains that completely reshape your sales process.

Why Platform Choice Matters

Many sales teams stumble when they underestimate the cost of a mismatched platform. Some platforms are too simple to scale beyond basic automations. Others are too complex, leaving non-technical teams overwhelmed and projects abandoned. Switching platforms midstream is not only disruptive—it’s expensive and time-consuming. Integration limitations, hidden in the fine print, often surface only after a team has invested weeks in setup.

The right platform, however, unlocks real productivity gains. I’ve seen companies scale from five to fifty automations without hiring additional staff. I’ve seen sales teams reduce errors through automated data transfers, and I’ve seen response times improve from hours to mere minutes. Those results come from aligning platform capabilities with team comfort and long-term strategy.

Breaking Down the Four Platforms

Zapier is often the starting point. It’s user-friendly, highly intuitive, and backed by the largest integration library in the market. For sales teams with little to no technical experience, it’s a great way to achieve quick wins—connecting CRMs, email platforms, and lead management tools in minutes. The trade-off, of course, is cost at scale and limited customization for advanced workflows.

Make.com represents the next step up. It’s a visual workflow builder designed for teams that need more sophisticated automations but still want a no-code interface. It handles complex branching logic, advanced data transformations, and high-volume workflows at a fraction of Zapier’s cost. But it comes with a steeper learning curve and requires more planning.

n8n is the open-source powerhouse. Unlike Zapier or Make.com, there are no artificial limits on workflow complexity or execution. It can be self-hosted, giving technical teams total control over security, customization, and cost. It’s ideal for organizations with developers or strong technical resources. The downside? It requires real expertise, both to implement and to maintain.

Finally, there’s Pipedream, which includes String. It blends accessibility with developer power, offering real-time event processing, API flexibility, and built-in coding support for JavaScript and Python. It’s the platform of choice for teams that want advanced, responsive automations but are comfortable getting hands-on with APIs and code when needed.

Matching Platforms to Your Team

The key to success is not asking which platform is “best,” but which is “best for us.” If your team is non-technical and just needs quick, reliable automations, Zapier is the natural fit. If you want advanced workflows without hiring developers, Make.com is the right middle ground. If you have developers or strong technical resources, n8n gives you unlimited control at a fraction of the long-term cost. And if your workflows demand real-time responsiveness and advanced API integrations, Pipedream is worth serious consideration.

Think carefully about your team’s technical comfort, the complexity of your use cases, your budget for scale, and your integration requirements. These factors should guide your decision far more than flashy features or marketing claims.

Taking the First Step

The best way to move forward is to experiment. Sign up for free accounts on two platforms and run the same simple workflow in each. For example, capture a new lead from your website, push it into your CRM, and trigger an automated welcome email. Watch how each platform handles it. Document the process, note the pain points, and gather feedback from your team.

Once you’ve seen the difference firsthand, you’ll know where to invest. Start small, prove the value quickly, and then scale. Over time, your automation strategy can evolve into a foundational pillar of your sales operations.

You can learn more by listening to my podcast episode for AI Tools for Sales Pros. Check out the episode here:

Join the B2B Sales Lab

If this episode leaves you curious—or perhaps a bit overwhelmed—remember that you don’t have to navigate these decisions alone. Inside the B2B Sales Lab, you’ll find sales professionals who are actively testing these platforms, sharing workflows, and troubleshooting challenges. It’s a private, member-led community where sales pros exchange real-world experience, not theory.

Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Whether you’re evaluating platforms, designing your first automation, or scaling to dozens of workflows, you’ll find actionable insights and peers who’ve been there before.

👉 You can join today with a free 90-day membership at b2b-sales-lab.com.

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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Two Tall Guys Talking Sales – Why Consistent Sales Strategies Win: Forecasting, Messaging, and Revenue Management – Episode 151

Two Tall Guys Talking Sales – Why Consistent Sales Strategies Win: Forecasting, Messaging, and Revenue Management – Episode 151

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey delve into the crucial role of deal qualification in driving sales success. From simple frameworks like BANT to advanced methodologies such as MEDDIC and MEDDPICCC, Kevin and Sean explain how consistent sales processes, value selling, and business acumen can sharpen forecasting, strengthen messaging, and ultimately accelerate revenue generation. Whether you’re managing a sales team or selling solo, this discussion will help you refine your sales strategies and improve your revenue management outcomes.

Key Topics Discussed

  • The cooking analogy for sales qualification – how preparing a meal mirrors building consistent sales processes 
  • Why full qualification matters – reducing forecast slippage, aligning solutions to customer needs, and driving predictable revenue generation.
  • BANT explained – Budget, Authority, Need, and Timeline as a simple framework for qualifying deals 
  • Beyond BANT – an overview of advanced methodologies such as SPIN, SPICED, and NEAT for value selling in complex deals 
  • Deep dive into MEDDIC and MEDDPICCC – why metrics, the economic buyer, and champions are essential for enterprise-level sales success 
  • The importance of sales management consistency – ensuring every salesperson in an organization qualifies deals with the same discipline 

Key Quotes

  • Kevin Lawson : “When you close things better, when you have more deal intelligence or customer intelligence or relationship intelligence gained through a qualifying methodology, you end up being better able to serve a customer.”
  • Sean O’Shaughnessey : “If you have five salespeople trying to qualify deals, you want them to qualify them the same way—consistency matters because it creates repeatable sales success.”
  • Sean O’Shaughnessey : “Every deal needs a champion. If you can get a champion to sell for you when you’re not there, you are far more likely to win.”

Additional Resources

  • HubSpot Blog: A Guide to Sales Qualification Frameworkshttps://blog.hubspot.com/sales/6-popular-sales-methodologies-summarized
  • The Qualified Sales Leader by John McMahon is an essential read on MEDDIC from one of the most successful sales leaders in software history. https://a.co/d/76089W7
  • Join the B2B Sales Lab for 90 days free and access practical community discussions on sales strategies, revenue management, and messaging. https://b2b-sales-lab.com

A Significant Actionable Item from this Podcast

Select and consistently implement one sales qualification framework across all your deals.
Whether you adopt BANT for simplicity or MEDDPICCC for enterprise-level selling, consistency in qualification builds stronger forecasts, improves customer alignment, and accelerates revenue generation. Decide on one methodology, train your team, and hold yourself accountable to using it every time.

Why You Should Listen

This episode is packed with practical insights for salespeople, managers, and business leaders committed to improving revenue management and sales success. Kevin and Sean take you from everyday analogies to advanced enterprise strategies, showing why consistent qualification is the backbone of predictable growth. If you want sharper sales processes, better forecasting, and stronger messaging that supports value selling, you won’t want to miss this conversation. Download now and start applying these proven sales strategies to your own pipeline.

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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