forecasting

AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

By Sean O'Shaughnessey

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.

Time is a salesperson’s most valuable asset.

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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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 – Why Consistent Sales Strategies Win: Forecasting, Messaging, and Revenue Management – Episode 151

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey delve into the crucial role of deal qualification in driving sales success. From simple frameworks like BANT to advanced methodologies such as MEDDIC and MEDDPICCC, Kevin and Sean explain how consistent sales processes, value selling, and business acumen can sharpen forecasting, strengthen messaging, and ultimately accelerate revenue generation. Whether you’re managing a sales team or selling solo, this discussion will help you refine your sales strategies and improve your revenue management outcomes.

Key Topics Discussed

The cooking analogy for sales qualification – how preparing a meal mirrors building consistent sales processes
Why full qualification matters – reducing forecast slippage, aligning solutions to customer needs, and driving predictable revenue generation.
BANT explained – Budget, Authority, Need, and Timeline as a simple framework for qualifying deals
Beyond BANT – an overview of advanced methodologies such as SPIN, SPICED, and NEAT for value selling in complex deals
Deep dive into MEDDIC and MEDDPICCC – why metrics, the economic buyer, and champions are essential for enterprise-level sales success
The importance of sales management consistency – ensuring every salesperson in an organization qualifies deals with the same discipline

Key Quotes

Kevin Lawson : “When you close things better, when you have more deal intelligence or customer intelligence or relationship intelligence gained through a qualifying methodology, you end up being better able to serve a customer.”
Sean O’Shaughnessey : “If you have five salespeople trying to qualify deals, you want them to qualify them the same way—consistency matters because it creates repeatable sales success.”
Sean O’Shaughnessey : “Every deal needs a champion. If you can get a champion to sell for you when you’re not there, you are far more likely to win.”

Additional Resources

HubSpot Blog: A Guide to Sales Qualification Frameworkshttps://blog.hubspot.com/sales/6-popular-sales-methodologies-summarized
The Qualified Sales Leader by John McMahon is an essential read on MEDDIC from one of the most successful sales leaders in software history. https://a.co/d/76089W7
Join the B2B Sales Lab for 90 days free and access practical community discussions on sales strategies, revenue management, and messaging. https://b2b-sales-lab.com

A Significant Actionable Item from this Podcast

Select and consistently implement one sales qualification framework across all your deals.
Whether you adopt BANT for simplicity or MEDDPICCC for enterprise-level selling, consistency in qualification builds stronger forecasts, improves customer alignment, and accelerates revenue generation. Decide on one methodology, train your team, and hold yourself accountable to using it every time.

Why You Should Listen

This episode is packed with practical insights for salespeople, managers, and business leaders committed to improving revenue management and sales success. Kevin and Sean take you from everyday analogies to advanced enterprise strategies, showing why consistent qualification is the backbone of predictable growth. If you want sharper sales processes, better forecasting, and stronger messaging that supports value selling, you won’t want to miss this conversation. Download now and start applying these proven sales strategies to your own pipeline.

From Reporting to Coaching: Elevate Your One-on-One Sales Meetings to Drive Performance and Trust

By Sean O'Shaughnessey

A one-on-one sales meeting is not a reporting meeting. It’s not about reviewing what already happened. And it’s definitely not about the manager doing most of the talking. The purpose of a one-on-one pipeline review is to develop the salesperson, surface challenges, and accelerate opportunities. If your one-on-ones are anything less, you’re leaving performance on the table.

Sales leaders often default to micromanagement.

Especially when the rep is new or struggling. But that approach backfires. It creates dependency and stifles problem-solving. The goal is to coach your reps into leading the meeting. That shift changes everything. When reps own the agenda and bring forward deal-level insights, they’re forced to think critically. That’s where growth happens.

If you’re leading a sales team or are a CEO playing the role of sales manager, you need to establish a clear structure. But the rep does the prep. You define the meeting cadence and format. Weekly or bi-weekly, depending on your velocity. You outline the sections: committed deals, stalled deals, and at-risk deals.

But the rep fills in the content. They come to the meeting ready to walk you through each opportunity, with specific updates and clear asks.

Preparation is non-negotiable. For both sides.

The salesperson should have updated their CRM before the meeting. The manager should have reviewed that data in advance. If either party shows up unprepared, the meeting becomes reactive.

A waste of time. And it erodes trust quickly.

Reps notice when you haven’t read the notes. They know when you’re winging it. And if they feel their effort isn’t valued, they’ll stop putting in the effort.

You want to create a culture where preparation is expected and rewarded.

The fastest way to management failure is to ask questions that could have been answered by reading the CRM. Instead, use that time:

To probe deeper.
Ask about the deal strategy.
Challenge assumptions.
Help salespeople spot gaps they missed.

That’s where your experience has real value.

It’s tempting to jump in and solve the problem. Especially when you see the red flags before the rep does. But resist the urge. Let them talk it through. Coach them toward the insight. Your job isn’t to close the deal; it’s to build someone who can. That means teaching them how to identify weak spots, how to pressure test a deal, and how to re-engage a stalled buyer. The real value of one-on-ones is in that development.

Think about how you coach.

Are you diagnosing for them? Or are you helping them diagnose for themselves? When a rep says “this deal is solid, no issues,” that’s a red flag. Every deal has risk. Your job is to help them uncover it. Ask: “What’s the biggest thing that could derail this?” Or “What’s the last thing the buyer said that gave you pause?” These questions surface the truth. And they teach reps to self-assess more effectively.

There’s a fine line between coaching and grading. You want reps to be honest about their pipeline without fear of judgment.

If a deal is weak, that’s not a character flaw. It’s a coaching moment.

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APIs Explained for Sales Leaders: Drive Growth Without Extra Headcount

By Sean O'Shaughnessey

A sales manager recently told me, “I have to copy the same prospect data into five different tools. There has to be a better way.” That frustration is more common than most sales leaders realize, and fortunately, there is a better way.

The reality is that sales teams are hemorrhaging productivity due to disconnected systems. Top performers spend hours manually entering data, bouncing between platforms, and correcting inevitable errors. This administrative overhead steals time from the only activity that drives revenue: selling.

At Oracle, TIBCO Software, and Red Hat, we used to call this “system integration.” Today, the language has shifted, and we call it APIs. But while the terminology may have evolved, the underlying solution remains powerful—and far more accessible than ever. APIs act like invisible bridges, allowing your tools to communicate seamlessly without human intervention.

Think of APIs as the waiter in a restaurant. Your CRM (the customer) tells the waiter what it wants. The waiter goes to the kitchen (the external service), retrieves the order, and delivers it back to the table. Your sales team never sees the behind-the-scenes work, only the results. That’s the beauty of APIs: they quietly enable speed, accuracy, and scale.

The impact on sales organizations is profound. With API integrations in place, companies reduce administrative work by huge percentages, improve data accuracy through automated syncing, and shrink research time from hours to minutes. Sales velocity climbs when tools communicate directly, and managers gain real-time pipeline visibility that simply isn’t possible otherwise.

No-code integration platforms like n8n, Zapier, Make.com, and Microsoft Power Automate make APIs accessible to every sales team. Whether it’s automating lead enrichment, triggering email sequences, streamlining forecasting, or even preventing churn, APIs unlock productivity and accuracy at every stage of the sales process. These aren’t theoretical benefits—they’re measurable gains that compound over time.

The real question isn’t whether your team can benefit from APIs, but whether you’re willing to make the leap. Ask the right questions of your vendors. Start small with one or two integrations. Document and test your processes. And most importantly, free your team from administrative busywork so they can focus on delivering value to customers.

The future of B2B sales isn’t about choosing between humans and AI. It’s about 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 below and consider subscribing to the podcast AI Tools for Sales Pros on your favorite podcast player.

Cut Through the AI Hype: Practical Definitions for Sales Professionals

By Sean O'Shaughnessey

Artificial intelligence is transforming sales, but too many leaders are investing in tools they don’t fully understand. The result? Costly mistakes, poor adoption, and missed opportunities. This episode of AI Tools for Sales Pros breaks down the three core technologies behind AI:

Machine Learning (ML),
Natural Language Processing (NLP),
Large Language Models (LLMs)

and explains them in plain language that every sales professional can use.

The episode compares the current AI confusion to the database revolution of the 1990s. Just as sales leaders once needed to grasp relational databases or virtualization to sell effectively, today’s leaders must understand AI fundamentals to buy, implement, and coach effectively. Without this knowledge, vendor meetings become traps where features outshine true solutions.

Why Sales Leaders Need to Understand AI

Vendors are selling “AI-powered” tools that are often just automation with marketing polish.
ROI depends on knowing what you’re really buying.
Sales reps look to leadership for clarity and coaching on new technologies.
Competitive advantage comes from strategic implementation, not just adoption.

The Three Core AI Technologies

Machine Learning (ML): The pattern recognition engine. It predicts outcomes by analyzing historical sales data. Use cases: lead scoring, deal risk analysis, forecasting.

Natural Language Processing (NLP): The communication translator. It helps machines understand and analyze human conversations. Use cases: call transcription, sentiment analysis, chatbots, and objection detection.

Large Language Models (LLMs): The content creation powerhouse. They generate human-like content at scale. Use cases: personalized emails, proposals, meeting prep, follow-ups.

When the Technologies Work Together

The magic happens when ML, NLP, and LLMs integrate. Imagine: ML identifies the best prospects, NLP uncovers their communication style, and LLMs create personalized outreach. Companies are seeing 30%+ response rates with this integrated approach.

Misconceptions and Realities

Myth: AI replaces humans. Reality: It augments judgment.
Myth: More AI equals better results. Reality: Focused use beats scattered adoption.
Myth: AI requires massive data. Reality: Many sales AI tools work with modest data sets.

Action Steps for Sales Leaders

Audit your current tools—identify which technologies you’re already using.
Apply the vendor evaluation framework before making new purchases.
Share these simplified definitions with your team.
Connect with peers in the B2B Sales Lab community to learn from real implementations.

AI competency isn’t about programming—it’s about making better buying decisions and leading your sales team strategically. The future of B2B sales is not humans vs. AI—it’s humans amplified by AI.

👉 Register for your free 90-day membership at b2b-sales-lab.com and join the conversation.

AI in B2B Sales Isn’t Optional Anymore

By Sean O'Shaughnessey

Several months ago, I was serving as a fractional VP of Sales for a $50 million manufacturing company. Their top salesperson was a 15-year veteran who knew the industry inside and out. Yet he was consistently being outsold by a competitor’s much newer hire. At first, it didn’t make sense until we discovered the reason.

The competitor’s rep wasn’t just more energetic or aggressive. They were AI-enabled. While my client’s rep was manually scrolling LinkedIn and drafting emails from scratch, the competitor’s rep was using AI tools to research prospects, craft personalized outreach, and prepare for meetings. In other words, the competitor had a partner working 24/7—freeing them to focus on what humans do best: building trust and closing deals.

That was the turning point. I realized we weren’t just competing against other salespeople anymore. We were competing against AI-enhanced sales teams.

The Most Urgent Technology Wave in Sales

Throughout my career, I’ve watched new technology waves disrupt the sales profession. Robotics transformed manufacturing in the 1980s. Solid modeling replaced drafting tables in the 1990s. Cloud computing reshaped IT in the 2000s.

Each time, early adopters gained the edge while laggards struggled to catch up. The AI wave is different for two reasons:

It’s broader: touching every aspect of sales, from prospecting to forecasting.
It’s faster: companies have months, not years, to adapt before the competitive gap becomes overwhelming.

AI in sales isn’t coming. It’s already here.

The Four Pillars of AI Sales Transformation

To make sense of AI’s role in sales, I use a framework I call the Four Pillars of AI Sales Transformation.

1. Efficiency Amplification

Salespeople lose hours each week on research, data entry, and administrative tasks. AI automates these repetitive activities, turning wasted time into revenue-generating capacity. If a rep with a $2 million quota spends 40% of their time on admin work, reclaiming even half of that time can translate into hundreds of thousands of dollars in additional revenue potential.

2. Personalization at Scale

Buyers expect relevance. AI enables sales teams to tailor outreach at a scale that was previously impossible. One client of mine went from producing 10 personalized emails per day to 500, each one referencing company news, industry pain points, or competitive dynamics. The result: higher engagement and faster response times.

3. Predictive Intelligence

AI spots patterns humans miss. It identifies which deals are at risk, when prospects are most likely to respond, and which leads are worth pursuing first. For one client, simply shifting demos to Tuesday afternoons increased conversion rates by 40%. When your competitors are guessing, AI gives you confidence.

4. Continuous Learning & Optimization

Unlike static playbooks, AI evolves. It analyzes win/loss data, tests messaging, and provides real-time coaching insights. One client discovered that pricing discussions were their biggest choke point. AI flagged the pattern, we built automated battlecards, and close rates improved by 18%.

Real-World Results

These aren’t theoretical benefits. In my own client work:

An AI-powered prospecting rollout increased appointment-setting rates from 8% to 23% in just six weeks.
A lost-deal analysis uncovered patterns that helped recover $2 million in the pipeline.

The reality is clear: companies already experimenting with AI are pulling ahead. Those who delay are watching the gap widen daily.

Three Things You Can Do This Month

If you’re ready to start, here are three immediate steps:

Audit your workflow. Identify one repetitive task you can automate—prospect research, meeting prep, or follow-up emails.
Pilot an AI tool. Start small with an affordable, no-code platform. Many cost less than $200/month.
Learn with others. Don’t navigate this change alone. Surround yourself with peers who are experimenting, learning, and winning with AI.

Join the B2B Sales Lab

The best way to accelerate your adoption is to connect with others on the same journey. That’s why we built the B2B Sales Lab, a private, member-led community for sales professionals who want actionable insights, not theory. It’s where strategy meets execution.

In the Lab, you can:

Ask real questions about sales challenges.
Share proven best practices.
Learn from other sales professionals and veteran leaders.

Your first 90 days are free. Join us today at b2b-sales-lab.com.

The future of B2B sales isn’t about choosing between humans and AI. It’s about humans amplified by AI. Those who adapt now will thrive. Those who wait may not get the chance to catch up.

To learn more, listen to this podcast on the subject.

B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

By Sean O'Shaughnessey

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

Hard-to-automate skills
Deployment-related skills
Scarce, high-utility skills
Skills hard for others to learn or replicate

Each of these aligns tightly with the demands of modern B2B sales.

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The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process

By Sean O'Shaughnessey

Many salespeople, sales managers, and CEOs face a unique problem. This issue concerns the sales process, particularly when specific steps are skipped. The challenge is common among sales teams across various industries, and there are different perspectives on its causes and solutions.

This issue is concerning since, according to Harvard Business Review, 28% of companies that master at least three stages of their sales process will see an increase in revenue growth. (https://hbr.org/2015/01/companies-with-a-formal-sales-process-generate-more-revenue). That same study states that companies that had trained their sales managers to manage their pipelines saw their revenue grow 9% faster than those that didn’t. But not just any training will do. Sales managers need targeted training to address specific pipeline management challenges.

Sometimes, the sales process might seem tedious, and salespeople may skip steps out of impatience or eagerness to close a deal. However, skipping these steps can lead to further complications down the line. When a sales team is not following the process that has been identified, it can disrupt the team’s rhythm and efficiency. Some might argue that this is a sign that the process needs to change or that more training is required.

This issue extends beyond the sales team. When a company hires a fractional VP of sales, it brings an outside perspective to evaluate its sales process. The fractional VP will often encounter resistance from the existing team, who may feel their industry is unique. While every business has its distinctive elements, the fundamentals of a sales process are universal.

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