Business growth

Two Tall Guys Talking Sales – Sales Planning 101: How to Crush Your Quota and Grow New Accounts – E108

By Sean O'Shaughnessey

Welcome back to Two Tall Guys Talking Sales! In this episode, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into the nuts and bolts of individual sales planning. This conversation moves beyond just hitting quotas—it’s about creating a personal strategy that drives you toward success. Whether you’re starting fresh in a new fiscal year or planning for growth, Kevin and Sean have you covered with actionable advice, real-world examples, and inspiration for developing your own winning sales plan. Get ready to sharpen your tools and plan to exceed your quota!

Key Topics Discussed

Building Your Sales Plan (2:00): Sean breaks down the critical elements of creating your personal sales plan, including setting a quota, calculating the number of deals you need to close, and how to push yourself beyond expectations.
Analyzing Your Existing Customer Base (4:10): Kevin emphasizes the importance of understanding your existing customers, maintaining relationships, and strategically growing accounts that can carry you through the year.
Knowing Your Competitors and Market (6:30): Both hosts discuss the significance of competitor analysis and knowing your market, down to the behaviors and needs of your customers.
Planning for New Accounts (9:00): Sean challenges listeners to add new accounts to their plan and start treating those prospective clients like they are essential to your financial future.
Collaborating with Marketing (11:00): Sean and Kevin stress the importance of working hand-in-hand with your marketing team to fill the gaps in your sales plan and generate quality leads.

Key Quotes

Sean (2:50): “If you’re supposed to do 50 deals to hit your million-dollar quota, guess what? You have to do 60. We’re going over quota—no excuses!”
Kevin (4:40): “Am I taking care of the customers that I know I should be taking care of? Yes or no. It’s really straightforward.”
Kevin (5:50): “Know who your competitors are, and know who you want to do business with. Don’t just rely on marketing to tell you—figure it out for yourself.”
Sean (9:55): “You need to think of these prospective accounts as your best friends. If they are important to your success, know everything about them.”

Additional Resources

If you missed last week’s episode on Building a Sales Plan That Works: Aligning Vision with Execution, go back and listen for an in-depth look at building sales strategies from a leadership perspective. https://sites.libsyn.com/458454/site/building-a-sales-plan-that-works-aligning-vision-with-execution

A Significant Actionable Item from this Podcast

Identify 20 new accounts you do not currently have a relationship with and begin learning everything about them—competitors, pain points, goals, and market behaviors. Integrating these targets into your sales plan today can set you up for growth and success as early as January.

Summary

This episode of Two Tall Guys Talking Sales is packed with valuable insights for every sales professional looking to take control of their personal sales plan. Kevin and Sean encourage you to meet your quota and exceed it by going the extra mile—analyzing existing customers, targeting new ones, understanding your competitors, and working closely with marketing to generate leads. Whether you’re an individual salesperson or a sales leader, this conversation will leave you energized and ready to tackle the coming months with a winning strategy. Don’t miss this episode!

Two Tall Guys Talking Sales – Building a Sales Plan That Works: Aligning Vision with Execution – E107

By Sean O'Shaughnessey

Join Kevin Lawson and Sean O’Shaughnessy, your hosts on Two Tall Guys Talking Sales, as they delve into the crucial topic of building a comprehensive corporate sales plan. Fresh off last week’s enlightening episode with Richard Cogswell, Kevin and Sean are back to share actionable strategies for creating a robust sales plan that aligns with corporate goals, ensures sales team success, and drives growth. Whether you’re a VP of Sales or a business owner looking to scale, this episode is packed with insights to help you reach your sales targets effectively.

Key Topics Discussed:

The Importance of Sales Plan Alignment (Approx. 01:32) Kevin explains why sales reps and leaders must understand and align with the company’s long-term vision, ensuring goals cascade from top-level leadership to every sales team member.
Bottom-Up vs. Top-Down Sales Planning (Approx. 03:17) Sean and Kevin outline the tactical approaches to sales planning, with bottom-up focusing on individual sales potential and top-down focusing on company-wide aspirations and limitations.
Risk-Adjusted Goal Setting (Approx. 02:55) Kevin highlights how to factor in both realistic and aspirational targets while accounting for potential risks, offering a pragmatic approach to sales planning.
Understanding Limiting Factors in Sales Growth (Approx. 06:30) Sean shares an example of a client that couldn’t scale due to manufacturing constraints, emphasizing the need to account for operational bottlenecks in the sales plan.
The Value of Discovery Questions (Approx. 08:45) Sean underscores the importance of including tailored discovery questions for different buyer personas, ensuring salespeople are prepared to ask the right questions during prospecting.

Key Quotes:

Kevin Lawson:
“As a VP of Sales, my compensation was directly tied to helping the board, the leader, the owner achieve their vision. What we’re doing is creating alignment between the company’s big picture and the sales team’s tactical execution.” (Approx. 01:32)
Sean O’Shaughnessy:
“When you’re thinking top-down, think about what your limitations are for delivering on those goals. It’s not just about setting lofty sales targets; it’s about asking, ‘How are we going to deliver on this?’” (Approx. 05:10)

Additional Resources:

Previous Episode:
If you missed last week’s discussion with Richard Cogswell on culture and developing sales plans, be sure to catch up for more insights that build upon today’s conversation.
https://sites.libsyn.com/458454/site/building-a-mission-led-sales-culture-insights-from-richard-cogswell

A Significant Actionable Item from this Podcast:

Write down the top 10 companies that fit your ideal client profile but aren’t currently customers. Challenge your sales team to convert at least one of these prospects into a paying customer by year-end. The simple act of documenting these targets can dramatically improve your chances of success by keeping everyone focused and accountable.

Summary:

In this episode of Two Tall Guys Talking Sales, Kevin and Sean lay out the blueprint for developing a high-impact sales plan that aligns with your company’s goals and sales targets. With practical examples and actionable advice, they explain how to approach sales planning from both the bottom-up and top-down perspectives, highlighting the importance of understanding your business’s limitations and opportunities for growth. If you’re looking to elevate your sales strategy, this episode is a must-listen!

Two Tall Guys Talking Sales – Building a Mission-Led Sales Culture: Insights from Richard Cogswell – E106

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey sit down with Richard Cogswell, a 20-year sales veteran and author who leads the APAC region in the FinTech space. Richard shares his journey from commission-only sales in the insurance industry to becoming a B2B sales leader in the complex world of payments. Together, they discuss the critical importance of developing a mission-led culture, the pitfalls of sales leadership without a plan, and actionable strategies for creating a structured sales environment.

Join the conversation as they explore how sales leaders can move beyond the typical financial-year focus and elevate their teams with clarity, focus, and purpose. Whether you’re a sales leader or a single contributor looking to up your game, this episode is packed with insights to help you build a more robust sales foundation.

Key Topics Discussed:

The Importance of a Go-to-Market Sales Plan (00:01:47): Richard highlights why many organizations lack an articulated sales strategy and the repercussions this can have on cross-functional alignment and growth.
From Surviving Year-to-Year to a Mission-Led Culture (00:04:22): The hosts dive into how sales leaders can shift from short-term financial targets to a long-term, mission-driven approach.
Creating a Structured Sales Environment (00:06:18): Richard explains the necessity of documenting your big bets and aligning your team with cross-functional partners.
Identifying and Empowering Sales Leaders (00:11:00): Learn how to recognize key players within your team and use them to foster growth and cohesion.
The Power of Salespeople Creating Their Own Plans (00:12:48): Richard shares the importance of involving sales reps in the planning process and how it strengthens accountability and execution.

Key Quotes:

Richard Cogswell: “If you’re a commercial leader and you don’t have a structured sales plan, I’m sorry, but that is your responsibility to create one. How else do you align your team and cross-functional leaders toward the same goals?” (00:03:18)
Sean O’Shaughnessey: “You have to have a plan. Kevin and I are often brought in as fractional VPs of sales, and the first thing we see is the absence of a plan, which is exactly why we’re needed.” (00:04:43)
Kevin Lawson: “I love what you said about getting beyond the fiscal year focus and building a mission-led culture. That’s a simple, but powerful, shift every sales leader needs to understand.” (00:10:31)

Additional Resources:

Richard Cogswell’s book, The Cultural Sales Leader: Sustaining People, Attaining Results, is available on Amazon, Barnes & Noble, and other retailers. https://a.co/d/1sc187j
Connect with Richard on LinkedIn for more insights into sales leadership and cultural transformation in business. https://www.linkedin.com/in/richardcogswell/

A Significant Actionable Item from this Podcast: Sales leaders should implement a one-page sales plan for their team. This document should clearly define the financial goals, top priorities, values and behaviors expected, and specific actions needed to achieve success. Ensure this plan is regularly revisited and adjusted to align with short-term and long-term goals.

Summary: In this episode, Richard Cogswell brings a wealth of experience to the table, sharing his journey from commission-only sales to leading an entire region in the FinTech industry. His insights into the necessity of structured sales plans, mission-led cultures, and empowering sales leaders are invaluable for anyone in sales leadership or aspiring to be. Whether you’re managing a team or just starting out, the principles Richard discusses can help take your sales strategy from surviving to thriving. Don’t miss this chance to learn how to build a focused, intentional sales culture that drives long-term success!

Two Tall Guys Talking Sales Podcast – Strategic Sales Planning: Finish Strong and Prepare for FY25 – E105

By Sean O'Shaughnessey

As the year winds down and football season takes over, Sean O’Shaughnessey and Kevin Lawson remind us that it’s time for sales leaders to focus on the coming year. In this episode of Two Tall Guys Talking Sales, Sean and Kevin dive into actionable strategies for building a strong foundation in FY25, including compensation plan design, strategic projects, and investing in your sales team. Whether you’re a sales leader, business owner, or manager, this episode provides expert advice on how to finish strong and gear up for the year ahead.

Key Topics Discussed:

The Importance of Sales Compensation Plans (00:01:57): Sean and Kevin highlight the need to deliver next year’s compensation plans by December 1st and the impact of “cliffs” and “escalators” on driving end-of-year sales.
Prioritizing Strategic Projects for FY25 (00:08:00): From technology investments to adding resources, the hosts explain how to plan for success beyond basic sales goals.
Incentivizing Sales Success Without Caps (00:04:38): Kevin discusses why capping commissions can limit growth, and how uncapped plans can drive higher performance and retention.
Skills Building as a Strategic Investment (00:09:22): Sean encourages sales leaders to invest in skill development, particularly for small businesses, to boost overall sales team performance.
Assessing Your Sales Organization (00:13:51): Sean and Kevin emphasize the value of conducting a sales assessment to identify areas for improvement before the new year begins.

Key Quotes:

Sean O’Shaughnessey: “The time to write your sales compensation plan is October 15th or November 1st so you can deliver it by December. This year is what we’re being graded on, so we need to finish strong.” (00:03:48)
Kevin Lawson: “If you’re trying to 3x, 4x, 5x your business, putting a cap on commissions will stall that growth. We need to incentivize success, not limit it.” (00:05:19)
Sean O’Shaughnessey: “It’s not just about closing deals, it’s about investing in your team’s skills so they can deliver more revenue next year.” (00:10:24)

A Significant Actionable Item from this Podcast:

Deliver your sales compensation plans by December 1st. Incorporate “cliffs” to incentivize end-of-year performance and use “escalators” to reward ongoing success throughout the year. This structure not only pushes deals forward but ensures your team is focused on finishing the year strong and starting the next with momentum.

Summary:

Don’t wait until January to plan your sales strategy! In this episode, Kevin and Sean break down the crucial elements you need to set your team up for success in FY25, from delivering well-timed compensation plans to strategic project planning and skills development. Tune in now for expert advice and practical tips on how to finish this year strong and hit the ground running next year.

Two Tall Guys Talking Sales Podcast – Sales Success and Growing Pains: How to Build Systems That Scale – E104

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey explore the complexities of rapid sales growth. While many companies aspire to grow, not all are ready for the operational strain accompanying success. The hosts share insights on scaling systems, optimizing sales operations, and ensuring growth doesn’t break your business. This episode offers actionable strategies for businesses facing fast-paced expansion, from onboarding salespeople to expanding infrastructure.

Key Topics Discussed:

Recognizing the Pain of Growth (00:01:00)
Sean discusses the challenge of managing growth when sales outpace operational capabilities, posing critical questions about when to add resources like marketing or legal support.
Building Systems That Scale (00:02:30)
Kevin shares how building robust, repeatable processes—whether hiring one salesperson or ten—ensures sustainable and scalable growth.
When to Hire Sales Support Staff (00:03:32)
The discussion highlights the importance of adding operational roles such as sales analysts or revenue operations personnel to ease the workload on sales teams.
Maximizing Sales Efficiency (00:07:14)
Sean advises identifying which tasks to delegate from high-performing salespeople to specialists, increasing overall efficiency and productivity.
Tailoring Sales Strategy to Industry Needs (00:09:26)
Kevin elaborates on how different industries may require unique sales strategies, emphasizing the need to adapt based on business size and market demands.

Key Quotes:

Sean: “We need to grow, but can the rest of the organization grow with us?” (00:05:00)
Kevin: “Growth is a cash event. Growth is a change event. When you 2x, 3x a business in sales, you often break things.” (00:02:48)
Sean: “Think about how much time high-performing people spend doing things that are not high-performing tasks, and figure out how you can take that off their plate.” (00:12:52)

A Significant Actionable Item from this Podcast:

Conduct a time audit for your sales team. Identify non-sales tasks that consume their time, such as data entry or order processing. Delegate these tasks to a dedicated admin or sales operations role. This can significantly boost productivity and allow your top performers to focus on closing deals.

Summary:

In this episode, Kevin and Sean break down the key challenges of scaling a business during periods of fast growth. They offer practical advice on creating efficient processes, hiring the right support staff, and ensuring your sales operations keep pace with your revenue expansion. Whether your company is rapidly expanding or preparing for future growth, this episode is packed with actionable insights that can help you maintain momentum without breaking your business. Tune in to learn how to balance growth and efficiency for long-term success!

Two Tall Guys Talking Sales Podcast – Daily Habits for Deepening Sales Relationships: A Guide for Busy Sales Professionals – E103

By Sean O'Shaughnessey

In this insightful episode, Kevin Lawson and Sean O’Shaughnessey delve into practical strategies for deepening relationships and boosting sales without extensive outreach efforts. Whether you’re a seasoned sales professional or just starting out, this episode is packed with actionable tips to enhance your sales approach by focusing on the people you already know.

Key Topics Discussed:

Building Relationships with Minimal Effort (00:01:03) – Strategies to maintain and strengthen relationships with minimal outreach, including personalized interactions beyond generic newsletters.
Utilizing Personal Interests in Sales (00:03:11) – How personal interests and hobbies can be leveraged to maintain contact with clients and build a deeper connection.
The Importance of Customized Communication (00:08:44) – Discuss how tailored communication can enhance customer relationships and trust.
Systematizing Relationship Management (00:12:51) – Sean’s methodical approach to managing relationships through strategic use of CRM and personalized content.
Sales as a Guiding Principle (00:13:00) – How consistent, targeted outreach is foundational to a successful sales strategy and organizational culture.

Key Quotes:

Kevin: “The currency of trust is what we’re building here… The idea that I’m passionate about running is an example of, Hey, we want to pay attention to our customers.” (00:06:10)
Sean: “Just send an article that made you think of them… This personal touch is what keeps the relationship strong and their interest in doing business with you alive.” (00:04:00)

Additional Resources:

Book: “Atomic Habits” by James Clear – referenced by Kevin as a core to building better processes – https://a.co/d/cHE8akb

A Significant Actionable Item from this Podcast:

Daily Personalized Outreach: Dedicate a few minutes daily to send personalized articles or messages to a few contacts. This habit keeps the relationship warm and ensures you remain top of mind, increasing the likelihood of continued business and referrals.

Summary

This episode is a gold mine for anyone looking to effectively maintain and grow their sales networks. Kevin and Sean break down the art of nurturing relationships with existing contacts through simple yet impactful daily habits. By integrating personalized communication and maintaining a consistent presence, sales professionals can foster deeper connections and ensure a robust network. If you want to refine your sales and relationship management approach, this episode is a must-listen.

Two Tall Guys Talking Sales Podcast – Sales Strategy Deep Dive: How to Align Offers with Client Expectations – E102

By Sean O'Shaughnessey

Join hosts Kevin Lawson and Sean O’Shaughnessey in a dynamic episode of “Two Tall Guys Talking Sales,” where they dive deep into the essential elements of crafting an effective sales strategy. Whether you’re a sales newbie or a seasoned pro, this episode promises insights into refining your approach to acquiring new clients and boosting your sales performance.

Key Topics Discussed:

Ideal Client Profiles (Approx. 00:01:00): Discover the power of tailoring your approach to fit the perfect client profile and why it’s the cornerstone of any successful sales strategy.
Messaging in Sales (Approx. 00:03:27): Learn the art of crafting messages that resonate with your target audience, ensuring your communication aligns perfectly with their expectations and needs.
Designing Compelling Offers (Approx. 00:06:31): Explore how to frame your products or services in a way that emphasizes their value and addresses the aspirational needs of your clients.
Strategic Alignment (Approx. 00:12:11): Understand the synergy between client profiles, messaging, and offers and how aligning these elements can lead to sales success.
Sales Process Optimization (Approx. 00:10:59): Gain insights into organizing your sales strategies to ensure they are effective, repeatable, and scalable.

Key Quotes:

Kevin: “If you’re a dentist and all you get is people with foot pain, you’re sending out the wrong message about your practice.” (Approx. 00:03:52)
Sean: “The goal for really selling and eliminating your competition and really setting yourself up for success is to teach them to aspire to something greater.” (Approx. 00:09:04)

Additional Resources:

“Strategic Selling” by Miller Heiman – A seminal book on sales strategies, mentioned for its impactful concepts that have shaped modern sales approaches. – https://a.co/d/iPykhyA
RAIN Group Sales Training – Recommended for those looking to further their understanding of sales aspirations and strategic customer alignment.

A Significant Actionable Item from this Podcast:

Reflect on Your Client Profiles: Take a moment to revisit and refine your ideal client profiles. This exercise will help ensure that your sales messaging and offers are perfectly tailored to meet your target audience’s specific needs and aspirations, significantly increasing your chances of closing more deals.

Summary:

In this episode, Kevin and Sean break down the intricate dance of aligning client profiles, messaging, and offers to craft a sales strategy that meets and exceeds expectations. Their conversation is filled with actionable advice backed by real-world examples and seasoned insights, making it a must-listen for anyone looking to enhance their sales effectiveness. Tune in to refine your approach and learn how to construct sales pitches that are heard and truly resonate.

Two Tall Guys Talking Sales Podcast – Preparing Salespeople for Success: A Deep Dive with Steve Caton – E96

By Sean O'Shaughnessey

Join hosts Kevin Lawson and Sean O’Shaughnessey as they welcome back Steve Caton for another insightful episode of “Two Tall Guys Talking Sales.” This week, they delve deeper into the world of part-time salespeople, discussing the essential tools, traits, and strategies that make them highly effective for businesses. Whether you’re a CEO, sales leader, or aspiring salesperson, this episode is packed with valuable advice and actionable tips.

Key Topics Discussed:

Preparing Part-Time Salespeople for Success (00:00:24): Steve Caton outlines the key factors in readying salespeople for part-time roles, emphasizing the importance of adaptability, trust-building, and research.
Traits of Effective Part-Time Salespeople (00:04:16): Discover the personality traits and experience levels that Steve looks for when recruiting part-time salespeople, including adaptability, organizational skills, and systematic approaches.
Measuring Success and Setting Expectations (00:07:22): Kevin and Steve discuss how to set and measure success metrics for part-time salespeople, focusing on sales activity and CRM usage.
Transitioning from Part-Time to Full-Time Salespeople (00:10:18): Learn about the process and considerations when a company is ready to transition from part-time to full-time sales roles.
Differentiating from Appointment Setting Services (00:11:58): Steve explains how his company focuses on the closer role, highlighting the need for leads and the differences from traditional appointment-setting services.

Key Quotes:

Steve Caton (00:01:46): “The salesperson needs to have shown that they’ve actually done some research on the company like they actually know about the business before they step in and start having the first conversation with the business owner.”
Sean O’Shaughnessey (00:03:26): “Every salesperson that’s looking for a job needs to be able to do those things as well. You need to say, I add value. I know I’m going to ask questions. I’m trying to learn the backstory of the company.”
Kevin Lawson (00:07:22): “How do you measure the success of a new salesperson that you’ve plugged into one of your first customers? What’s the dialogue there?”

Summary:

This episode of “Two Tall Guys Talking Sales” is a must-listen for anyone interested in the dynamics of part-time sales roles and how they can significantly impact business growth. Steve Caton shares his expertise on preparing salespeople, measuring their success, and transitioning them into full-time roles. With practical advice and real-world examples, this episode offers a comprehensive guide for sales leaders and business owners aiming to optimize their sales strategies. Tune in now to learn from the best and take your sales team to the next level!

Two Tall Guys Talking Sales Podcast – From Zero to Sales Hero: Steve Caton’s Strategies for Small Business Growth – E95

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey are joined by Steve Caton, CEO and Founder of Altezza Solutions. Steve shares his insights on how to build effective sales systems for emerging growth companies and provides a unique perspective on hiring part-time experienced salespeople. Dive into this episode to learn about the challenges and solutions in developing a robust sales strategy for small to mid-sized businesses.

Key Topics Discussed

Introduction to Steve Caton and Altezza Solutions (00:00:15)
- Steve discusses the inception of Altezza Solutions and his motivation behind starting the company.
Challenges of Hiring Salespeople for Emerging Companies (00:02:36)
- Steve talks about the common difficulties small companies face when hiring their first salesperson and offers an innovative part-time solution.
Importance of Sales Infrastructure (00:04:55)
- The hosts and Steve explore the critical components of a sales infrastructure necessary for a sales team to thrive.
Salesperson Integration and Training (00:11:44)
- Steve outlines a detailed onboarding process for new salespeople, emphasizing the first three months of integration.
Preparing for Business Exits (00:07:12)
- Discussion on how business owners can enhance their company’s valuation by building a self-sufficient sales team before planning an exit.

Key Quotes

Steve Caton: “The convincing piece wasn’t as hard as I thought it would be because it was almost like the reaction was, ‘Dang, I never even thought about that. That makes a ton of sense.’” (00:03:58)
Kevin Lawson: “Sales organizations that are evolved, mature, robust, they attract talent…let’s build the organization we all want to work for that attracts the right talent.” (00:10:15)
Sean O’Shaughnessey: “One of the challenges that I have heard from my business broker friends is that when the CEO is the salesperson…they really struggle with the selling of the company.” (00:06:53)

Summary

Don’t miss this enlightening episode with Steve Caton, where he shares invaluable advice on building a scalable sales infrastructure and the benefits of hiring part-time sales professionals. Whether you’re a business owner looking to strengthen your sales team or a sales professional seeking new strategies, this episode offers practical insights and actionable steps. Tune in next week for more in-depth discussions with Steve on creating successful sales organizations.

Building a Successful Sales Team: A Guide for CEOs and Managers

By Sean O'Shaughnessey

You can overcome obstacles and significantly improve your sales performance with the right mindset, strategies, and tools. For salespeople, sales managers, and CEOs of small companies, the journey to sales excellence is paved with lessons and insights that can be invaluable in improving management capabilities and driving revenue growth.

The sales process is a critical aspect of any business. It’s the engine that drives revenue and growth and the platform on which customer relationships are built. However, businesses often encounter a unique problem in their sales process. The problem isn’t necessarily about the product or service being sold, the market, or the competition. Rather, it’s about the people involved in the process—the salespeople.

Being a salesperson is a challenging profession. It requires a unique set of skills, a deep understanding of the product or service being sold, and a certain level of resilience to face the inevitable rejections that come with the job. But more than that, it requires a mindset that embraces growth, learning, and continuous improvement.

Read the rest of the article…