From 10 to 100 Customers: Scaling Your Sales Process for Growth

From 10 to 100 Customers: Scaling Your Sales Process for Growth

By Sean O'Shaughnessey

For founders of companies, the journey of a business is a narrative of evolution, growth, and constant adaptation. As salespeople, sales managers, and CEOs, we are all too familiar with the challenges and triumphs that punctuate this journey. In the world of sales, one of the most critical turning points is the transition from acquiring your first ten customers to expanding your customer base to 50 or even 100. This pivotal moment sets the trajectory of a business and is a key focus of our discussion.

When you’re starting, the founding team is focused on acquiring those first ten customers. They’re trying to find their footing in the market, identify their target audience, and refine their product or service offering. You might be customizing your product or service for each customer to ensure it fits their specific needs. However, as you aim for the next level of growth, it’s crucial to start thinking about systemizing your sales process. This will ensure efficiency and prepare you for the next level of growth. 

To scale effectively, company leaders need to standardize their product or service offering. While customization can be beneficial in the early stages, it becomes impractical and inefficient as your customer base grows. The key here is to create a product or service that can be sold repeatedly with minimal adjustments. This streamlines the sales process, making it easier for others to sell the product or service.

In the early stages of a business, the founders might be the ones doing all the selling. But as the company grows, this becomes less feasible. To reach a larger number of customers, you need to bring others on board to sell for you. This is where standardization comes into play. By standardizing your product or service, you make it easier for others to understand and sell it. 

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

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

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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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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Two Tall Guys Talking Sales – Breaking the Silos: Aligning Sales and Marketing for Real Revenue Growth – Episode 147

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.

Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

Two Tall Guys Talking Sales – Building a Sales Powerhouse—The 3 Most Underrated Skills with Jeff Parris – Episode 143

By Sean O'Shaughnessey

Sales isn’t about persuasion but service, resilience, and growth. In this episode of Two Tall Guys Talking Sales, co-hosts Kevin Lawson and Sean O’Shaughnessey welcome sales leader and former professional athlete Jeff Parris to explore the fundamental skills that separate elite salespeople from the rest. Drawing on decades of experience, Jeff shares three often-overlooked yet foundational competencies that drive sales success, and they’re not what you’d expect. Whether you’re a VP of Sales building a high-performance team or a seller looking to level up, this episode delivers sharp insights on value selling, business acumen, and sales management excellence.

Key Topics Discussed

  • Why great salespeople see themselves as servants first (approx. 04:00)
    Jeff outlines why a “motivation to serve” mindset creates stronger client relationships and more consistent revenue generation.
  • Ego Drive vs. Ego Trip: Understanding the will to win without arrogance (approx. 07:30)
    Learn how ego drive, a hunger to persuade for the buyer’s benefit, builds durable sales performance.
  • Curiosity as the gateway to sales mastery (approx. 10:15)
    Jeff and Sean dig into why curiosity fuels continuous improvement and business acumen across every sales process.
  • How to coach the “accidental salesperson” into a top performer (approx. 11:45)
    Kevin asks how people without formal sales backgrounds can thrive by developing the right mindset.
  • Sales leaders as talent architects: Building high-performance teams (approx. 02:00)
    Jeff draws on his athletic past to share what makes a sales team championship-worthy.

Key Quotes

  • “Sales isn’t something we do to people, it’s something we do for people.”
    — Jeff Parris (04:00)
  • “The real goal of a great salesperson is: ‘Mr. Prospect, let me help you solve that problem.”
    — Sean O’Shaughnessey (05:55)
  • “Having the right people, with the right skills, in the right seats makes winning so much easier.”
    — Kevin Lawson (03:36)
  • “Curiosity leads to better solutions. Every interaction is a chance to learn and improve your craft.”
    — Jeff Parris (10:50)

Additional Resources

A Significant Actionable Item from this Podcast

Evaluate your team (and yourself) on the “Service–Drive–Curiosity” Triad.
Start by asking three questions:

  1. Does this salesperson show a genuine desire to serve the customer’s goals?
  2. Do they take pride in persuading with purpose, not just for commission but impact?
  3. Are they consistently seeking to learn more about the customer, the industry, and their performance?

Use these questions in your next 1-on-1 or team coaching session to align your talent strategy with the kind of sales success that sustains revenue generation.

Why You Should Listen to This Episode

If you’re tired of surface-level sales advice, this conversation will challenge your thinking and expand your toolkit. Jeff Parris brings clarity, conviction, and humility to what it means to lead with purpose in today’s complex B2B landscape. From building elite sales teams to refining your individual sales strategy, this episode is packed with practical wisdom for leaders, sellers, and anyone serious about mastering the craft of sales. Tune in now and discover the underestimated traits that drive extraordinary outcomes.