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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Navigating the Sales Maze: Overcoming Missed Steps in Your Sales Process

Navigating the Sales Maze: Overcoming Missed Steps in Your Sales Process

By Sean O'Shaughnessey

The challenges for a salesperson or a sales manager are numerous. One such challenge that often arises during the sales process is the realization that a crucial step has been skipped. This situation is not uncommon and is faced by many salespeople. However, it’s not a moment for reprimanding or pulling out an accountability chart. Instead, it’s a moment of realization and an opportunity to rectify the error to avoid ending up in the ‘no decision lane.’

I have written about the importance of skipping stages of the sales process elsewhere on this site, most recently in “The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process,” where I remind you that, according to the Harvard Business Review, 28% of companies that master at least three stages of their sales process will see an increase in revenue growth.

When you recognize you’ve missed a step in your sales process, it resembles backing up a train. You’ve got a lot of cars put together, but one is out on its own. Addressing this situation requires a specific style and approach. As a sales leader, your focus should be on the next step in the process. Have you covered this step from a question in the sales meeting? It’s important to ask questions like, “What is next? What is missing? What is now?” 

As a salesperson, if you realize you’ve missed a step, address it head-on. This approach allows you to rectify your error and builds trust with your prospect by demonstrating transparency and accountability. 

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

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!

Building High-Performing Sales Teams: Accountability, Strategy, and Success

Building High-Performing Sales Teams: Accountability, Strategy, and Success

By Sean O'Shaughnessey

Navigating the complexities and ensuring a robust and productive team are pivotal to achieving sustained success in sales. Accountability within a sales team requires pinpointing underperformance and creating an environment where feedback is constructive and growth is nurtured. The notion that no team member should be surprised by a change in their employment status underscores the importance of transparent communication. Setting realistic expectations and having regular discussions ensures that salespeople know where they stand and what is expected of them.

Underperformance can stem from various factors, but a common issue highlighted is the lack of skills. Identifying this gap is the first step toward rectification, paving the way for targeted coaching and development. Coaching isn’t just about improving skills; it’s about instilling the right behaviors that drive success. This is particularly crucial in small businesses where the owners might juggle multiple roles, potentially overlooking critical aspects of their operations, including sales.

The dialogue also touches upon the importance of diversifying strategies beyond a single mode of customer engagement. For instance, relying solely on email without integrating calls can limit a salesperson’s effectiveness. Similarly, focusing too intensely on a single key account to the detriment of prospecting new clients can jeopardize overall sales performance.

Sales managers play a crucial role in facilitating the development of their team members, not only by setting expectations but also by actively participating in joint sales calls and understanding the challenges their salespeople face. Unfortunately, many sales managers haven’t engaged in such activities with their team members in years, highlighting a gap in leadership engagement that can contribute to underperformance.

Peer accountability, celebrating small wins, and fostering a culture where successes are recognized and rewarded contribute significantly to a healthy sales environment. These practices motivate salespeople and help to identify those struggling, offering them the support needed to improve. It’s a collective effort, emphasizing that sales is not just about individual achievements but about lifting the entire team, reflecting the adage that a rising tide lifts all boats.

Therefore, Addressing underperformance is not just about identifying weaknesses but creating an ecosystem where salespeople are supported, skilled, and motivated to excel. It involves a comprehensive approach, from ensuring adequate training and development to fostering a culture of accountability and support.

For sales managers and CEOs, the key takeaway is the importance of being actively involved in their team’s development, understanding their challenges, and providing the resources and support necessary for success. Sales is a complex and demanding field, but with the right strategies and a supportive environment, outstanding results are possible.

Actionable items that you can use today!

  1. Evaluate Communication and Expectations: Initiate a comprehensive review of your current communication practices and the clarity of expectations within your sales team. Ensure that every member clearly understands their goals, the metrics by which they are evaluated, and the consequences of underperformance. This could involve revising job descriptions, performance metrics, or the regularity and format of feedback sessions.
  2. Implement a Peer Accountability System: Start the process of establishing a peer accountability system by organizing a team meeting to discuss its benefits. Encourage your sales team to share their successes and challenges openly, and pair team members to serve as accountability partners. This system should aim to foster a supportive environment where salespeople can learn from each other and motivate one another toward achieving their sales targets.
  3. Develop a Mini-Coaching Plan: Identify at least one salesperson on your team who may be struggling or showing signs of underperformance. Design a short, targeted coaching plan to address their specific challenges, whether they be skill-based or motivational. This plan could include shadowing a high-performing team member, attending a specific training session, or setting up regular coaching meetings to work on identified areas of improvement.