The sales profession is challenging. You need to work hard at it to succeed. You need to learn from the best. You need to improve your skills continuously. If you think you can sell since you are a hit at parties and have a lot of friends, you may soon find that you are a failure as a salesperson. Blunt truth:
because the sales profession is so hard, you have to focus on doing everything in sales very well, or you will be considered a failure.
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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.
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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Sales leaders today often fall into the trap of using artificial intelligence tools randomly rather than systematically. This sporadic usage is like owning a Swiss Army knife but only using the bottle opener; you miss out on ninety percent of the available value. AI’s real power comes not from isolated tools but from integrating capabilities across every stage of your sales processes. When mapped correctly, AI accelerates every interaction, shortens sales cycles, and makes revenue generation more predictable.
Random AI adoption leads to inconsistent results. Some reps use it effectively, while others revert to manual methods under pressure, resulting in uneven performance. Systematic AI integration, however, compounds improvements across the entire sales cycle. Data captured at one stage strengthens the next, creating a virtuous cycle of sales success that is scalable, measurable, and sustainable. The outcome is not just faster deals, but stronger business acumen and more consistent revenue management.
The ten-stage AI sales process framework provides a structured way to apply AI:
Each stage leverages AI differently, from intent data analysis in prospecting to AI-driven customer success monitoring post-close. Integration ensures that research informs outreach, discovery guides scoping, and validation improves proposals. By connecting the entire workflow, sales teams gain predictable processes and continuous optimization opportunities.
Process-based implementation builds competitive advantage. Competitors can replicate isolated AI tools, but systematic integration across sales strategies and sales management creates a differentiated approach that scales with growth. Consistency across the team reduces dependency on individual skill differences, enhances messaging, and strengthens value selling.
The measurement framework behind this approach ensures continuous improvement. Stage-specific conversion rates, velocity metrics, and data quality indicators guide refinements. Weekly reviews, monthly AI effectiveness assessments, and quarterly adjustments keep teams aligned while maximizing ROI from AI investments. Over time, these optimizations compound, creating a performance engine that drives long-term revenue generation.
The future of B2B sales isn’t choosing between humans and AI. It’s humans amplified by AI. Let’s build that future together.
If you’d like to explore this topic in more depth, there’s a podcast episode that covers all of this information and more. You can find the link to the episode here and consider subscribing to the podcast AI Tools for Sales Pros on your favorite podcast player.
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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A VP of Sales recently confided in me: “We have six different AI tools, but our reps are still doing manual work. What went wrong?”
This is the AI tool proliferation problem. Sales leaders often collect tools without a strategy, mistaking a pile of features for a cohesive system. It’s like buying a hammer, screwdriver, saw, and drill without realizing you’re actually trying to build a house. An effective AI stack means integration. When tools work together, they amplify each other’s value. When they don’t, they add complexity, confusion, and wasted money.
Random tool adoption is rampant across sales organizations. Teams chase shiny new software, often ending up with overlapping features, siloed data, and productivity lost to tool-switching. Instead of solving problems, the stack itself becomes the problem.
But when built strategically, the benefits are profound. Integrated systems reduce manual data entry, accelerate response times, and deliver actionable insights for reps. Three well-chosen, well-connected tools can outperform six isolated ones. Integrated stacks also improve adoption rates by providing consistent interfaces and reducing training overhead.
To avoid the chaos of random adoption, I use a five-layer framework for structuring sales AI tools:
These layers aren’t just categories; they’re connected through data flows and integration principles. Each layer enhances the next, creating a system that scales intelligently with your team.
Your foundation layer usually consumes about half of your AI stack budget, but it’s worth it. Clean, structured data is the lifeblood of every other tool. From there, intelligence and automation layers drive the bulk of ROI by improving deal velocity, conversion rates, and rep efficiency.
Content tools and optimization layers build on that foundation, ensuring customer-facing communication remains sharp while performance is continually refined. When done right, this phased approach allows organizations to see value in months, not years.
Too many organizations make predictable mistakes: choosing tools for features rather than integration, underestimating training and adoption costs, or layering new tools on top of dirty data. Others rush implementation without testing, or ignore governance and compliance until it’s too late. The result? Expensive tools with low adoption and little measurable impact.
The lesson is simple: treat your AI stack like architecture. Every decision influences the system’s stability and scalability for years to come.
These examples prove the point: success isn’t about tool count, it’s about fit, flow, and integration.
Companies with strategic AI stacks create barriers that their competitors can’t easily replicate. Data integration, consistent workflows, and continuous optimization compound value over time. The earlier you get your architecture right, the stronger your long-term advantage becomes.
And remember: the future of sales isn’t about humans versus AI. It’s about humans amplified by AI.
If you want to go deeper into this topic, listen to Episode 7 of AI Tools for Sales Pros: Choosing the Right AI Stack for Your Sales Organization. You’ll find it on your favorite podcast player. Be sure to subscribe so you don’t miss the next episode: The AI Sales Process Map.
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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AI isn’t replacing salespeople, it’s making them more effective. The real risk isn’t losing your job to AI; it’s losing to a competitor who uses AI better than you do. Sales professionals who integrate AI into their workflow will outperform those who don’t.
It’s not about technology taking over but about using technology to gain an edge. The market is becoming increasingly competitive, and the most efficient salespeople will emerge victorious.
Every minute spent on administrative tasks is a minute not spent selling. AI helps reclaim those lost hours. Tools that automate writing, scheduling, and research allow salespeople to focus on what matters: building relationships and closing deals. If you’re not leveraging AI to increase productivity, you’re leaving opportunities on the table.
Sales emails need to be clear and professional. AI-powered writing assistants ensure your messages are polished and effective. A poorly written email can cost you a deal. AI tools catch grammatical mistakes, improve clarity, and even suggest more effective phrasing. This isn’t just about looking professional; it’s about being understood.
If your message isn’t clear, it won’t convert.
Presentations are another time-consuming task. AI can generate professional decks in minutes. Instead of spending hours designing slides, salespeople can focus on developing effective strategies. AI-powered tools create branded, structured presentations based on simple inputs. This ensures consistency while saving time. Sales professionals who utilize AI for presentations can focus on delivering insights rather than formatting slides.
CRM systems are the backbone of sales operations. AI enhances CRM by automating data entry, tracking customer interactions, and suggesting next steps. Salespeople often struggle with keeping CRM data updated. AI reduces this friction by automatically capturing and organizing information. A well-maintained CRM leads to better forecasting and stronger customer relationships.
If your CRM doesn’t have AI capabilities, it’s time to upgrade.
AI-driven insights enable sales managers to make more informed decisions, rather than relying on instinct. Managers can use AI to analyze performance trends, identify coaching opportunities, and predict revenue outcomes. AI doesn’t replace leadership; it enhances it.
Sales managers who adopt AI can build stronger teams and achieve better results. Ignoring AI in sales management is a strategic mistake.
Lead generation is another area where AI adds value. AI-powered tools can analyze vast amounts of data to identify high-potential prospects. Instead of spending hours researching leads, salespeople can receive AI-generated recommendations. This allows for more targeted outreach and higher conversion rates. AI doesn’t just find leads, it finds the right leads.
Sales follow-up is often inconsistent. AI ensures follow-ups happen at the right time with the right message. Automated reminders and AI-generated responses keep deals moving forward.
A well-timed follow-up can be the difference between closing a deal and losing it. AI helps salespeople stay on top of their pipeline without relying on memory.
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In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey build on last week’s discussion of qualification methodologies and take the conversation further—into how these frameworks should live inside your CRM. From aligning sales processes with the buyer’s journey to enforcing accountability at each stage, this conversation offers practical strategies that every sales leader and salesperson can implement. Expect a deep dive into sales management, revenue generation, sales processes, and how value selling thrives when marketing and sales teams work in sync.
Embed your qualification methodology directly into your CRM, tied to each stage of your sales process.
Don’t let critical deal information reside inside spreadsheets or Word docs; configure your CRM so progression requires those qualification questions to be answered. This not only improves sales accuracy but also enhances revenue management, ensures consistency across your team, and creates alignment with marketing resources to drive value selling.
This episode of Two Tall Guys Talking Sales is a must-listen for anyone serious about building sustainable sales success. Sean and Kevin reveal how sales strategies such as qualification methodologies come to life when fully integrated into CRM-driven sales processes. You’ll learn why sales management must prioritize data consistency, how business acumen prevents late-stage deal disasters, and how aligning messaging between sales and marketing fuels stronger revenue generation. If you want practical insights on improving your sales processes and elevating your organization’s performance, download this episode today and start putting these best practices to work.
A sales manager recently told me something that stuck: “We went from twenty hours per week of manual work to two hours. Our lead response time dropped from four hours to four minutes.” That dramatic transformation wasn’t magic—it was automation.
The reality is that sales teams today have more automation tools available than ever before. But with options like Zapier, Make.com, n8n, and Pipedream, the real challenge isn’t whether you should automate—it’s choosing the right platform for your team. Each one comes with strengths, limitations, and unique philosophies. Get that choice wrong, and you’ll waste time, money, and buy-in. Get it right, and you’ll see efficiency gains that completely reshape your sales process.
Many sales teams stumble when they underestimate the cost of a mismatched platform. Some platforms are too simple to scale beyond basic automations. Others are too complex, leaving non-technical teams overwhelmed and projects abandoned. Switching platforms midstream is not only disruptive—it’s expensive and time-consuming. Integration limitations, hidden in the fine print, often surface only after a team has invested weeks in setup.
The right platform, however, unlocks real productivity gains. I’ve seen companies scale from five to fifty automations without hiring additional staff. I’ve seen sales teams reduce errors through automated data transfers, and I’ve seen response times improve from hours to mere minutes. Those results come from aligning platform capabilities with team comfort and long-term strategy.
Zapier is often the starting point. It’s user-friendly, highly intuitive, and backed by the largest integration library in the market. For sales teams with little to no technical experience, it’s a great way to achieve quick wins—connecting CRMs, email platforms, and lead management tools in minutes. The trade-off, of course, is cost at scale and limited customization for advanced workflows.
Make.com represents the next step up. It’s a visual workflow builder designed for teams that need more sophisticated automations but still want a no-code interface. It handles complex branching logic, advanced data transformations, and high-volume workflows at a fraction of Zapier’s cost. But it comes with a steeper learning curve and requires more planning.
n8n is the open-source powerhouse. Unlike Zapier or Make.com, there are no artificial limits on workflow complexity or execution. It can be self-hosted, giving technical teams total control over security, customization, and cost. It’s ideal for organizations with developers or strong technical resources. The downside? It requires real expertise, both to implement and to maintain.
Finally, there’s Pipedream, which includes String. It blends accessibility with developer power, offering real-time event processing, API flexibility, and built-in coding support for JavaScript and Python. It’s the platform of choice for teams that want advanced, responsive automations but are comfortable getting hands-on with APIs and code when needed.
The key to success is not asking which platform is “best,” but which is “best for us.” If your team is non-technical and just needs quick, reliable automations, Zapier is the natural fit. If you want advanced workflows without hiring developers, Make.com is the right middle ground. If you have developers or strong technical resources, n8n gives you unlimited control at a fraction of the long-term cost. And if your workflows demand real-time responsiveness and advanced API integrations, Pipedream is worth serious consideration.
Think carefully about your team’s technical comfort, the complexity of your use cases, your budget for scale, and your integration requirements. These factors should guide your decision far more than flashy features or marketing claims.
The best way to move forward is to experiment. Sign up for free accounts on two platforms and run the same simple workflow in each. For example, capture a new lead from your website, push it into your CRM, and trigger an automated welcome email. Watch how each platform handles it. Document the process, note the pain points, and gather feedback from your team.
Once you’ve seen the difference firsthand, you’ll know where to invest. Start small, prove the value quickly, and then scale. Over time, your automation strategy can evolve into a foundational pillar of your sales operations.
You can learn more by listening to my podcast episode for AI Tools for Sales Pros. Check out the episode here:
If this episode leaves you curious—or perhaps a bit overwhelmed—remember that you don’t have to navigate these decisions alone. Inside the B2B Sales Lab, you’ll find sales professionals who are actively testing these platforms, sharing workflows, and troubleshooting challenges. It’s a private, member-led community where sales pros exchange real-world experience, not theory.
Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Whether you’re evaluating platforms, designing your first automation, or scaling to dozens of workflows, you’ll find actionable insights and peers who’ve been there before.
👉 You can join today with a free 90-day membership at b2b-sales-lab.com.
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.
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?
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 a sales turnaround isn’t just about fixing numbers; it’s about transforming the business. It’s about realigning expectations, rebuilding internal trust, and creating a structured, sustainable path forward.
If you’re a CEO, sales manager, or a key salesperson in your organization, the pressure to reverse a sales slump can feel overwhelming. However, the truth is that turnarounds aren’t made in a sprint; they’re built through clarity, consistency, and effective communication.
Too often, sales leaders make the mistake of focusing only on the downward trend. They get caught up in the urgency of the numbers and forget that the real challenge lies in managing upward, setting expectations with executive leadership, and aligning them with reality.
If your sales team is underperforming, your internal stakeholders are your new audience. Just as with external prospects, you need to manage their expectations with a clear, actionable plan.
Instead of viewing upper management as critics, think of them as clients. What do they need to believe in this turnaround? What information do they need to trust your leadership? Start by building a high-level outline. Avoid over-engineering the details in the early stages. Focus on where you want to go, then reverse-engineer the steps to get there.
Every turnaround starts from a rear position. That means your first job is to stop the downward momentum. Before you can scale revenue, you need to stabilize it. That requires a clear definition of success, agreed upon by everyone involved.
If not, revise it. A stretch goal is fine. A fantasy is not.
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