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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AI in B2B Sales Isn’t Optional Anymore

AI in B2B Sales Isn’t Optional Anymore

Several months ago, I was serving as a fractional VP of Sales for a $50 million manufacturing company. Their top salesperson was a 15-year veteran who knew the industry inside and out. Yet he was consistently being outsold by a competitor’s much newer hire. At first, it didn’t make sense until we discovered the reason.

The competitor’s rep wasn’t just more energetic or aggressive. They were AI-enabled. While my client’s rep was manually scrolling LinkedIn and drafting emails from scratch, the competitor’s rep was using AI tools to research prospects, craft personalized outreach, and prepare for meetings. In other words, the competitor had a partner working 24/7—freeing them to focus on what humans do best: building trust and closing deals.

That was the turning point. I realized we weren’t just competing against other salespeople anymore. We were competing against AI-enhanced sales teams.

The Most Urgent Technology Wave in Sales

Throughout my career, I’ve watched new technology waves disrupt the sales profession. Robotics transformed manufacturing in the 1980s. Solid modeling replaced drafting tables in the 1990s. Cloud computing reshaped IT in the 2000s.

Each time, early adopters gained the edge while laggards struggled to catch up. The AI wave is different for two reasons:

  1. It’s broader: touching every aspect of sales, from prospecting to forecasting.
  2. It’s faster: companies have months, not years, to adapt before the competitive gap becomes overwhelming.

AI in sales isn’t coming. It’s already here.

The Four Pillars of AI Sales Transformation

To make sense of AI’s role in sales, I use a framework I call the Four Pillars of AI Sales Transformation.

1. Efficiency Amplification

Salespeople lose hours each week on research, data entry, and administrative tasks. AI automates these repetitive activities, turning wasted time into revenue-generating capacity. If a rep with a $2 million quota spends 40% of their time on admin work, reclaiming even half of that time can translate into hundreds of thousands of dollars in additional revenue potential.

2. Personalization at Scale

Buyers expect relevance. AI enables sales teams to tailor outreach at a scale that was previously impossible. One client of mine went from producing 10 personalized emails per day to 500, each one referencing company news, industry pain points, or competitive dynamics. The result: higher engagement and faster response times.

3. Predictive Intelligence

AI spots patterns humans miss. It identifies which deals are at risk, when prospects are most likely to respond, and which leads are worth pursuing first. For one client, simply shifting demos to Tuesday afternoons increased conversion rates by 40%. When your competitors are guessing, AI gives you confidence.

4. Continuous Learning & Optimization

Unlike static playbooks, AI evolves. It analyzes win/loss data, tests messaging, and provides real-time coaching insights. One client discovered that pricing discussions were their biggest choke point. AI flagged the pattern, we built automated battlecards, and close rates improved by 18%.

Real-World Results

These aren’t theoretical benefits. In my own client work:

  • An AI-powered prospecting rollout increased appointment-setting rates from 8% to 23% in just six weeks.
  • A lost-deal analysis uncovered patterns that helped recover $2 million in the pipeline.

The reality is clear: companies already experimenting with AI are pulling ahead. Those who delay are watching the gap widen daily.

Three Things You Can Do This Month

If you’re ready to start, here are three immediate steps:

  1. Audit your workflow. Identify one repetitive task you can automate—prospect research, meeting prep, or follow-up emails.
  2. Pilot an AI tool. Start small with an affordable, no-code platform. Many cost less than $200/month.
  3. Learn with others. Don’t navigate this change alone. Surround yourself with peers who are experimenting, learning, and winning with AI.

Join the B2B Sales Lab

The best way to accelerate your adoption is to connect with others on the same journey. That’s why we built the B2B Sales Lab, a private, member-led community for sales professionals who want actionable insights, not theory. It’s where strategy meets execution.

In the Lab, you can:

  • Ask real questions about sales challenges.
  • Share proven best practices.
  • Learn from other sales professionals and veteran leaders.

Your first 90 days are free. Join us today at b2b-sales-lab.com.

The future of B2B sales isn’t about choosing between humans and AI. It’s about humans amplified by AI. Those who adapt now will thrive. Those who wait may not get the chance to catch up.

To learn more, listen to this podcast on the subject.

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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Adapting to the New Sales Landscape: The Importance of Omni-Channel Outreach

Adapting to the New Sales Landscape: The Importance of Omni-Channel Outreach

Are you still relying on trade shows as your primary sales driver? The sales landscape has undergone a seismic shift. Those packed convention halls and endless rows of booths no longer serve as the bedrock of business development they once were.

Let’s talk about what works in today’s sales environment. Building an effective outbound pipeline isn’t just an option anymore – it’s your survival toolkit. But here’s the challenge: how do you stand out in a market where everyone’s fighting for attention?

Your unique value proposition makes all the difference. Yet many sales professionals miss a crucial point: your value proposition isn’t static. What resonates with a manufacturing client might fall flat with a distribution company. Have you tailored your message to address each industry’s pain points?

Think about your last prospecting campaign. Did you give up after four or five attempts? Research shows it takes 12 to 16 touches before prospects typically respond. This gap between persistence and practice often determines success or failure in modern sales.

The game has changed. Your prospects live in an omnichannel world. They check email between Zoom calls, scroll LinkedIn during lunch, and scan their phones throughout the day. How are you showing up in their digital world?

Consider this: every unanswered email or phone call might be a messaging problem. Are you talking about your features when you should be solving your prospects’ problems? Your prospects don’t care about your product specifications. They care about their challenges, their goals, and their bottom line.

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Two Tall Guys Talking Sales Podcast – From Microphones to Mountains – Reflecting on 100 Episodes of Sales Wisdom – E100

Two Tall Guys Talking Sales Podcast – From Microphones to Mountains – Reflecting on 100 Episodes of Sales Wisdom – E100

Join hosts Kevin Lawson and Sean O’Shaughnessey in this milestone 100th episode of “Two Tall Guys Talking Sales.” They take a nostalgic trip down memory lane, revisiting the evolution of their podcast from simple LinkedIn live events to a thriving sales discussion platform on Spotify and Apple Podcasts. They delve into their personal growth, the transformative insights gained, and the invaluable lessons they’ve shared across 100 episodes.

Key Topics Discussed:

  • Evolution of the Podcast [00:00:21]: Kevin and Sean reflect on the technological and methodological shifts they’ve embraced to enhance their podcast experience.
  • Insights on Sales Excellence [00:01:35]: Sean shares his journey of continuous learning in sales, emphasizing the wisdom imparted by Kevin and its impact on his professional development.
  • Role of Content Creation [00:03:11]: Kevin discusses the significance of creating and repurposing valuable content, drawing parallels with daily writing practices to improve skill.
  • Interviews with Industry Experts [00:04:14]: The hosts highlight the diverse insights gained from interviews with visionaries across various sectors, from SaaS founders to business coaches.
  • Future of the Podcast [00:08:31]: Looking ahead, Kevin outlines their aspirations to scale the podcast’s impact and deepen listener engagement.

Key Quotes:

  • Kevin [00:00:00]: “It’s basically a stack of wires and plastic…a lost and found of sorts for electronics equipment.”
  • Sean [00:01:35]: “Listening to Kevin explain sales is insightful…I have learned an immense amount in the last 100 episodes.”

Additional Resources:

Previous episodes on building a comprehensive sales process.

  1. https://sites.libsyn.com/458454/site/e1-inaugural-episode-why-should-a-company-assess-its-practices-in-sales
  2. https://sites.libsyn.com/458454/site/e2-how-do-you-determine-your-companys-sales-objectives-each-year
  3. https://sites.libsyn.com/458454/site/e3-are-your-sales-representatives-consistently-hitting-their-assigned-quotas
  4. https://sites.libsyn.com/458454/site/e4-how-do-you-compensate-your-salespeople
  5. https://sites.libsyn.com/458454/site/e5-do-you-have-a-documented-sales-process-that-is-followed-all-the-time
  6. https://sites.libsyn.com/458454/site/e6-how-do-salespeople-retain-client-information-and-document-sales-opportunities
  7. https://sites.libsyn.com/458454/site/e8-can-your-salespeople-clearly-communicate-your-unique-selling-proposition-what-makes-you-different-than-your-competition
  8. https://sites.libsyn.com/458454/site/e9-do-you-have-a-dashboard-view-into-the-major-determinants-of-sales-success
  9. https://sites.libsyn.com/458454/site/e10-do-you-feel-you-have-the-right-salespeople-to-get-you-where-you-want-to-go
  10. https://sites.libsyn.com/458454/site/e11-does-your-organization-hold-salespeople-accountable-for-lack-of-performance

Summary:

This 100th episode is a celebration and a testament to continuous improvement and shared growth in the sales world. Kevin and Sean unpack the layers of learning they’ve experienced and the wealth of knowledge they’ve gathered from various experts. Whether you’re a seasoned sales professional or a newcomer to the field, this episode offers a wealth of practical advice, humor, and insights that can transform your approach to sales and leadership.

A Significant Actionable Item from this Podcast:

Adopt the practice of discussing and refining your craft regularly. As highlighted by Kevin, talking about your sales strategies and processes, much like writers improve by writing daily, can significantly enhance your expertise and execution in sales.

To understand if your company is doing a great job in sales, take this quick and easy 10-question assessment: https://salesxceleration.com/sales-agility-assessment/?locationid=26671639

Driving Sales Success through Collaborative Learning and Knowledge Sharing

Driving Sales Success through Collaborative Learning and Knowledge Sharing

Aiming to increase revenue and boost productivity in sales processes, sales managers and company CEOs are constantly searching for effective strategies to streamline their operations and ensure optimal results. One such strategy involves conducting sales meetings for educational purposes. These meetings focus on enhancing knowledge and skills, and this is where the real game begins. 

Imagine a sales meeting where, instead of a mundane round-up of weekly activities, there’s an engaging discussion about a new book that can potentially revolutionize the sales process. Picture a team of four or five salespeople, including you, each reading two chapters of a book overnight. The next day, everyone shares the high-level takeaways from their assigned chapters. This practice allows the team to consume an entire book’s content in a day and empowers each member to become an authority on the subject matter because they’re teaching others. The exercise is educational, promotes team collaboration, and enhances communication skills. 

This approach can be extended beyond books to other areas, such as market research. For instance, if a company is looking to enter a new vertical, different aspects of the industry, like market influencers, challenges, and political, economic, and legal factors, can be assigned to team members for research. Each member returns their findings to the team, comprehensively understanding the new market. This practice is not merely busy work; it’s sales-driving work that benefits the entire team and accelerates learning about the new market.

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Maximizing Productivity in Sales Meetings: Key Principles and Best Practices

Maximizing Productivity in Sales Meetings: Key Principles and Best Practices

Sales meetings are the lifeblood of any sales-driven organization, providing an essential forum for communication, collaboration, and strategy development. Yet, despite their significance, many salespeople, managers, and CEOs struggle to conduct productive and efficient meetings. This issue often stems from a lack of understanding of key meeting principles and best practices, particularly in the areas of time management, content planning, and participant engagement.

The adage “time is money” holds especially true in sales. Every minute counts, and wasted time equates to lost opportunities. This is why punctuality is of the utmost importance. A meeting that starts late or runs over time is disrespectful to participants and detrimental to the team’s overall productivity. 

To avoid this pitfall, sales leaders should ensure they always arrive early to meetings and start them on time, without exception. This requires careful planning and preparation, as well as a commitment to respecting the time and schedules of others. The same principle applies to the end of the meeting. Sales leaders should always strive to conclude meetings on time, which requires careful meeting agenda management and a willingness to keep discussions focused and on track.

Content planning is another crucial aspect of effective meeting management. Just as a ship needs a compass to navigate the seas, a meeting needs an agenda to guide its proceedings. A well-crafted agenda provides a clear structure for the meeting and helps to keep discussions focused and productive. It also sets clear expectations for participants and helps to ensure that all relevant topics are covered.

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Proactive Coaching: The Key to Unlocking Exceptional Sales Performance

Proactive Coaching: The Key to Unlocking Exceptional Sales Performance

A shift is occurring away from simply correcting problems after they’ve happened toward a more proactive and developmental approach to coaching sales teams. This evolution in strategy empowers sales leaders, CEOs, and managers to not only meet but also exceed their targets through effective team management and personal development.

The concept of continuous improvement in sales begins with a focus on coaching. Unlike traditional reactive methods, modern sales leadership emphasizes coaching as a tool for ongoing development rather than merely correcting errors. This proactive coaching involves setting strategic goals with sales teams and using performance reviews—not as a critique but as a platform for growth and future planning. This method mirrors practices from top professionals in various fields who, regardless of their success, regularly receive coaching to enhance their performance.

Applying a coaching mindset to sales involves recognizing each team member’s individual needs and strengths. This personalized approach ensures that all team members, from the highest performers to those who might be struggling, receive the guidance they need to improve. The dialogue between a sales leader and their team shifts from what went wrong to what can be optimized, fostering a culture of continuous learning and adaptation.

An important part of this coaching process is the practical application of strategic planning, such as using quarterly business reviews (QBRs) to assess past performance and set proactive goals for future achievements. These sessions provide a structured framework for both leaders and salespeople to reflect on successes, learn from challenges, and plan actionable steps for ongoing improvement.

Leadership in sales also extends beyond internal team dynamics to personal development. Sales leaders are encouraged to invest in their own skills and capabilities to better serve their teams. This commitment to personal growth is crucial as it models the importance of lifelong learning to their teams, thereby instilling a similar mindset in their salespeople.

Effective sales leadership thus requires a dual focus: enhancing the team’s capabilities while simultaneously improving one’s own leadership skills. This approach not only achieves better sales outcomes but also builds a more resilient and adaptive sales organization, where both leaders and team members are committed to continuous improvement and excellence in their craft.

The role of a sales leader today is not just about managing a team but about actively participating in and fostering an environment of growth and excellence. By adopting a coaching mentality and focusing on both team and personal development, sales leaders can create dynamic teams that meet their current sales targets and are equipped to handle future challenges, ensuring sustained success and growth in the competitive market.

Here are a few actionable suggestions that a sales leader can do today!

  1. Schedule a Strategic Coaching Session: Identify a sales team member who could benefit from targeted coaching. Set up a one-to-one meeting for this week, focusing not on past shortcomings but on potential growth areas and setting actionable goals.
  2. Review and Refine Sales Metrics: Take a closer look at the metrics currently used to evaluate your team’s performance. Consider whether these truly capture the critical drivers of success or if they need adjustment to better reflect and promote your sales organization’s strategic goals.
  3. Initiate a Personal Development Plan: Reflect on your own leadership skills and identify areas for personal growth. Commit to a specific action, such as enrolling in a leadership workshop, starting a new book on advanced sales strategies, or scheduling regular check-ins with a mentor to enhance your leadership effectiveness.
Building High-Performing Sales Teams through Strategic Alignment

Building High-Performing Sales Teams through Strategic Alignment

The challenge of aligning the right people with the right organizational roles is paramount. As sales leaders and CEOs of small companies, understanding the intricacies of building and maintaining a proficient sales team is crucial for driving growth and achieving success.

The concept of having the “right people in the right seats” is not just a matter of recruitment but an ongoing process of evaluation, development, and strategic alignment. It’s essential to recognize that the adequacy of a sales team is not solely dependent on individual capabilities but also on how these individuals fit within the broader sales strategy and organizational culture.

Compensation plans, customer relationship management (CRM) systems, and the overarching sales infrastructure play significant roles in enabling sales teams to perform at their best. However, the foundation of a high-performing sales team lies in the continuous investment in people. This involves identifying talent and fostering an environment that promotes learning, growth, and adaptation.

Training and development are often overlooked aspects of sales management. Surprisingly, a significant number of sales professionals and leaders go years without receiving formal training. This gap in skill development can lead to stagnation and inefficiency. Therefore, organizations must prioritize ongoing education and training to keep their sales teams agile and competitive.

Furthermore, it is critical that individual roles align with the organization’s goals. This may involve reevaluating existing roles, responsibilities, and processes to ensure they contribute effectively to the sales strategy. Sometimes, the solution does not lie in hiring new talent but in optimizing the current team’s structure and roles to leverage their strengths more effectively.

Performance improvement plans (PIPs) and the concept of “top-grading” the sales team highlight the importance of accountability and continuous improvement. While PIPs can be a tool for addressing performance issues, they should not be the first resort. Instead, leaders should focus on setting clear expectations, providing the necessary resources and support, and fostering a culture of excellence.

Sometimes, the issue may not be with the sales personnel but with the systems, processes, or even the leadership approach. Before making drastic decisions, such as replacing team members, it’s worth taking a step back to assess whether the organization provides the right environment, tools, and guidance for the team to succeed.

Ultimately, building and managing an effective sales team is an intricate process that requires a balanced approach. It involves ensuring that you have the right people in place and that these individuals are equipped, motivated, and aligned with the organization’s goals. As sales leaders and managers, it’s essential to identify and address gaps, foster a culture of continuous learning and improvement, and strategically align team structures and processes to drive sales performance.

For salespeople, sales managers, and CEOs of small companies, understanding these dynamics and adopting a holistic approach to sales management can significantly enhance their team’s effectiveness and their organization’s ability to achieve its sales objectives.

Actionable items that you can do today

  1. Evaluate Your Team’s Composition: Take a moment to assess the current structure of your sales team. Identify whether each member is in the role that best suits their skills and where they can contribute the most to the team’s objectives. This could involve one-on-one discussions to understand their goals, strengths, and areas for improvement.
  2. Initiate a Training Needs Analysis: Conduct a thorough training needs analysis to identify gaps in skills and knowledge within your sales team. This should cover everything from product knowledge to sales techniques and the use of CRM systems. Based on this analysis, outline a tailored training program to address these gaps and elevate your team’s performance.
  3. Review and Adjust Compensation Plans: Analyze your current compensation and incentive structures to ensure they align with your organizational goals and sales targets. Adjustments might be necessary to better motivate your team and encourage the behaviors and outcomes you wish to see. This could mean introducing new performance bonuses, adjusting commission rates, or implementing non-monetary rewards that drive motivation.
  4. Implement a Sales Enablement Strategy: Start developing or refining your sales enablement strategy to ensure your sales team has the tools, resources, and content they need to succeed. This could involve updating sales playbooks, improving CRM processes, or investing in new sales enablement technology. The goal is to make it easier for your sales team to sell effectively and efficiently.