collaboration

Energize and Motivate: Essential Tips for an Effective Sales Kickoff Meeting

By Sean O'Shaughnessey

Before the year comes to a close, it’s time for sales teams and their leaders to prepare for the annual kickoff meeting. Don’t wait until December to start this process. If you have 50 or more people to invite, you may have to plan 6-9 months in advance. If your group is smaller (under 50), you should start planning by late September or early October.

This crucial event sets the stage for the upcoming year, establishing goals, strategies, and the motivation necessary to hit the ground running. Whether you are a salesperson, a sales manager, or the CEO of a small company, organizing an effective kickoff meeting is imperative to ensure a successful year ahead.

The first step in planning your annual sales meeting is to choose an appropriate venue. While it may be tempting to hold the meeting in your usual office space, it’s beneficial to opt for a location outside of your daily work environment. This helps to minimize distractions and fosters a creative atmosphere.

A nearby hotel or a conference center can serve as an excellent venue. The key is to find a place where your team can focus entirely on the meeting without the usual interruptions from their day-to-day responsibilities.

Once the venue is secured, it’s time to think about who should be in attendance. While the primary focus will be on your sales team, consider including key personnel from other departments such as marketing, IT, and customer service. These individuals play a crucial role in supporting the sales process and can provide valuable insights and updates that will help your sales team achieve success. Additionally, involving them in the kickoff meeting promotes a sense of unity and collaboration across the company.

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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

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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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.

Unlocking Sales Success: The Power of KPIs in Sales Processes

By Sean O'Shaughnessey

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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Two Tall Guys Talking Sales – Future-Proofing Your Sales with the Right Tech Stack – E115

By Sean O'Shaughnessey

In this thought-provoking episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive into the transformative power of technology in sales and operations. From the essentials of adopting a CRM to leveraging AI and automation, Kevin and Sean discuss how modern businesses can streamline operations, boost productivity, and prepare for the future. Whether you’re managing a small team or a large enterprise, this episode will provide actionable insights into creating an integrated tech stack that supports growth and resilience.

Key Topics Discussed

The Importance of a CRM System (Approx. 00:01:00)
- Why every organization needs a CRM to centralize and share data across teams, from sales to manufacturing.
- How a CRM can prevent revenue loss during sales team transitions.
Building an Integrated Tech Stack (Approx. 00:03:00)
- Understanding the interconnectedness of CRM, ERP, and project management tools.
- Simplifying operations with modern, cloud-based solutions.
Preparing for the AI Revolution (Approx. 00:04:00)
- How AI and machine learning are redefining operational workflows.
- Why having an AI strategy is essential for staying competitive.
Forecasting and Automation (Approx. 00:09:00)
- Leveraging technology to improve forecasting, pipeline management, and resource allocation.
- Automating routine tasks for efficiency and scalability.
The Role of Sales and Marketing Alignment (Approx. 00:11:00)
- Why sales and marketing collaboration is critical for success.
- How technology bridges the gap between these teams.

Key Quotes

Sean O’Shaughnessey:
“Your journey to 2035 starts right now. By staying on outdated tools, you’re not just behind—you’re making it harder to catch up later.” (Approx. 00:06:06)
Kevin Lawson:
“Technology is now part of the fabric of how we do business. If you want to grow and scale—or even just survive—adopting the right tools is the right battle to fight.” (Approx. 00:02:34)
Sean O’Shaughnessey:
“Revenue solves all problems in companies, but only if your systems are set up to support it.” (Approx. 00:12:23)

Additional Resources

McKinsey Report on AI in Business: September 2024 Edition.
HubSpot Marketplace: Tools to integrate CRM with calling apps and social media management platforms.
Ninety.io: Software for tracking KPIs and achieving quarterly goals.

A Significant Actionable Item from this Podcast

Start with Your CRM:
Evaluate your current CRM system (or lack thereof) and its integration with other business tools. Focus on centralizing data and enabling seamless communication between teams. This single step can drastically improve productivity, forecasting accuracy, and cross-functional collaboration.

Why You Should Listen

This episode of Two Tall Guys Talking Sales is a must-listen for anyone looking to future-proof their business. Kevin and Sean offer practical advice and actionable strategies to help you streamline operations, adopt cutting-edge technologies, and align your team for success. Whether you’re planning for 2025 or 2035, the insights shared in this episode will set you on the path to achieving your goals.

Tune in and discover how to take your sales operations to the next level!

The Secret to Sales Success: Effective Management and Qualification of MQLs and SQLs

By Sean O'Shaughnessey

The concept of leads is familiar to sales and marketing novices and experts. However, leads are not created equal. There are Marketing Qualified Leads (MQL) and Sales Qualified Leads (SQL). The differences between these two types of leads and the approach to handling them can significantly impact the efficiency and success of your sales pipeline.

The journey of a lead typically begins with the marketing team. They craft messages and campaigns to attract potential customers, drawing them towards the company. These potential customers or leads are known as Marketing Qualified Leads (MQLs). MQLs are individuals who have shown interest in the company’s product or service but have yet to be vetted for sales-readiness. They may have responded positively to the company’s marketing efforts by downloading a case study, signing up for a newsletter, following the company on social media, or a wide variety of other criteria that can be unique to each selling organization.

Unfortunately, just because a lead has shown interest does not mean they are ready to make a purchase. This is where the sales team comes in. Their role is to qualify these leads further, turning them into Sales Qualified Leads (SQLs). SQLs are leads the sales team has determined are ready for direct sales engagement. They have been vetted and have shown a clear interest and willingness to hear about the company’s offering from a sales perspective.

While marketing messages are designed to attract and engage a broad audience, the sales approach is more personal and more targeted. Sales focuses on building a relationship with the individual, understanding their unique needs, and demonstrating how the product or service can meet those needs.

Miscommunication or differing expectations can result in leads being passed along that are not truly sales-ready. This can waste time and resources and even damage potential customer relationships. It’s important for sales and marketing to work together, communicate effectively, and have a clear understanding of what constitutes a qualified lead.

One way to navigate this challenge is to establish clear criteria for MQLs and SQLs. What actions or behaviors indicate that a lead is ready to move from marketing to sales? This might include downloading certain resources, attending webinars, or requesting a product demo. By defining these criteria, both teams can ensure they’re on the same page and that leads are passed along at the appropriate time.

Salespeople should also understand how a lead became an MQL. What attracted them to the company? What information have they consumed? This understanding can inform the sales approach and help the salesperson build a relationship with the lead.

Communication between sales and marketing doesn’t end when a lead becomes an SQL. Salespeople should provide feedback to their marketing colleagues about the leads they’re receiving. If certain leads aren’t panning out, it’s important to communicate this so that marketing can adjust their strategies accordingly. Similarly, marketing should be open to feedback and willing to collaborate with sales to refine their lead qualification process.

In the end, marketing and sales have the same goal: to generate revenue for the company. By working together to manage and qualify leads effectively, they can ensure they’re both working towards this common goal.

With clear communication, collaboration, and a shared understanding of what makes a lead sales-ready, marketing and sales can streamline the sales pipeline and drive success.

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Building a High-Performing Sales Team: The Benefits of Recognizing Effort and Results in Sales Meetings

By Sean O'Shaughnessey

Sales drives the engine of any B2B business. Enhancing sales strategies and management capabilities is crucial to success for salespeople, sales managers, and CEOs of small companies. One aspect of this involves rewarding effort and results during sales meetings. This practice motivates the sales team and encourages them to strive for better performance.

Salespeople are naturally competitive and driven, but they also appreciate recognition. While a paycheck is important, it’s also essential for salespeople to feel valued and appreciated for their efforts. This recognition can come in various forms, from verbal praise to tangible rewards. It’s important to remember that recognition should not be limited to monetary rewards. The simple act of acknowledging someone’s hard work and contributions can be incredibly motivating.

A sales meeting is an opportune moment to recognize and reward your sales team’s efforts. It’s not just about discussing targets and strategies; it’s also a chance to celebrate successes, however big or small. These meetings can be used as a platform to highlight the best practices and strategies employed by the team members, fostering a culture of learning and improvement.

Every salesperson has a unique approach and strategy. If nothing else, they experiment with different ways to share the benefits of their product or ask a particular discovery question. By sharing these individual successes or failures during meetings, sales teams can learn from each other, thus promoting a collaborative and supportive environment. The sales leader may prompt these discussions, but the actual learning comes from the experiences and strategies the salespeople share.

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Two Tall Guys Talking Sales Podcast – Leading with Generosity- The Servant Leadership Approach to Sales with Tom Daly – E93

By Sean O'Shaughnessey

Welcome to another enriching episode of “Two Tall Guys Talking Sales,” where hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the art of sales with special guest Tom Daly from Focus Insights Group. In this episode, we explore the concept of servant leadership in sales and how giving more can ultimately lead to receiving more in business and personal growth.

Key Topics Discussed:

Servant Leadership in Sales [00:01:00 – 00:10:00]: Tom Daly discusses the importance of building productive referral networks and how servant leadership has helped him succeed in sales.

The Power of Giving Freely [00:05:00 – 00:08:00]: A detailed exploration of how giving without expecting immediate returns can foster long-term business relationships and personal satisfaction.

Balancing Generosity with Business Acumen [00:05:20 – 00:06:30]: Kevin probes the delicate balance between generosity and ensuring business viability.

Community and Collaboration [00:06:43 – 00:07:33]: The significance of a supportive community within the sales acceleration network, emphasizing collective success over individual gains.

Sales as a Helping Profession [00:08:21 – 00:09:52]: Sean reflects on the philosophy that sales should focus on helping and solving problems rather than just transactional interactions.

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Driving Sales Success through Collaborative Learning and Knowledge Sharing

By Sean O'Shaughnessey

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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