customer relationships

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 – Managing the Maverick: How to Lead Top Sales Performers Without Breaking Team Culture – Episode 146

By Sean O'Shaughnessey

When a top-performing salesperson refuses to follow the rules, tensions flare, and your culture might suffer. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey tackle a question straight from their B2B Sales Lab community: What do you do with a sales rockstar who drives the rest of the team nuts? If you’ve ever struggled with managing high-output, low-alignment team members, this conversation is packed with valuable insights, practical strategies, and real-world advice to help you strike a balance between performance and healthy team dynamics. Tune in for battle-tested tips on sales management, building a high-integrity sales culture, and protecting your company’s long-term revenue generation strategy.

Key Topics Discussed

Establishing Clear Norms in Sales Teams – Why your “top dog” needs to play by the same rules as everyone else, and how undefined expectations damage sales processes (Approx. 02:00)
The Power of Documented Standards and Culture Alignment – How lack of structure in small businesses creates room for chaos—and what to do about it (Approx. 03:30)
Tactical Solutions for Managing Lone Wolves – Real examples of how to realign high performers through mentorship and responsibility (Approx. 09:00)
Creating a Unified Sales Culture Without Crushing Performance – Why culture eats strategy for breakfast, especially in sales teams (Approx. 04:30)
Using Silence, Expectations, and Consistency to Set Boundaries – Kevin shares how saying “no” and standing firm protects team cohesion and customer relationships (Approx. 12:00)

Key Quotes

“Culture is probably the most important thing you possibly can have—and it starts with setting clear expectations.”
— Sean O’Shaughnessey (Approx. 06:05)
“Sales culture will eat strategy for breakfast. Culture always wins in the long run.”
— Kevin Lawson (Approx. 04:39)
“Sometimes you have to accept a little current pain to create future gain for your entire organization.”
— Kevin Lawson (Approx. 13:00)
“If you’re the person who colors outside the lines and won’t adjust… maybe you just don’t belong here.”
— Sean O’Shaughnessey (Approx. 08:30)

Additional Resources

Learn more about the B2B Sales Lab community: https://b2b-sales-lab.com

A Significant Actionable Item from this Podcast

Assign a High-Performer as a Mentor to Drive Culture Alignment
If you’re dealing with a rule-breaking top performer, try this: assign them as a mentor to a junior rep. This strategic move puts them in a leadership position where they must model the very behavior they’ve been resisting, updating the CRM, following your sales strategies, and representing your company messaging. This peer responsibility often encourages cultural realignment without confrontation.

Why You Should Listen to This Episode

This episode is a must-listen for sales managers, business owners, and team leaders wrestling with the dilemma of performance vs. process. Sean and Kevin don’t just talk theory—they give real, implementable strategies that can help you protect your sales culture, enforce consistent sales management practices, and drive long-term revenue success. If you’re aiming for scalable growth without sacrificing team cohesion, this episode delivers practical wisdom and a few gut-check moments. Hit play and discover how to bring even the most independent salespeople back into the fold—without losing their fire.

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

By Sean O'Shaughnessey

Building an effective sales pipeline requires a shift in strategy. Traditional cold calling has become increasingly ineffective, with decision-makers ignoring unsolicited calls and emails.

In the spring of 2021, Bank of America Corp.’s Merrill Lynch Wealth Management unit banned trainee brokers from making cold calls. According to the Wall Street Journal, it is hard to succeed with cold phone calls in an era when no one picks up. Merrill executives said personal referrals lead to a response around 40% of the time, but less than 2% of people who are cold-called even answer the phone.

Sales teams must adopt a more strategic approach, focusing on relationships rather than volume-based outreach. The key is leveraging existing networks to create warm introductions, significantly improving engagement rates and overall success.

Cold outreach has become expensive and inefficient, and the time spent dialing numbers, leaving voicemails, and sending emails that never get opened results in diminishing returns. Many executives no longer answer unknown calls, and email filters automatically sort cold outreach into spam. Even when messages get through, recipients are skeptical, assuming they are generated by automation rather than a genuine human connection. In reality, sales professionals must find a better way to reach their target audience.

Relationship-based selling offers a more effective alternative. Salespeople should focus on leveraging their connections instead of reaching out to strangers. This approach involves identifying key contacts who can provide warm introductions to potential prospects. These “super connectors” are individuals with strong networks and the ability to facilitate meaningful introductions. By tapping into these relationships, sales teams can bypass the skepticism associated with cold outreach and start conversations with credibility.

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Two Tall Guys Talking Sales – Prepping for Q2 – Getting Ahead, Catching Up, and Staying on Track – E129

By Sean O'Shaughnessey

As the first quarter comes to a close, sales leaders and professionals must assess their performance and gear up for the challenges and opportunities ahead in Q2. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the essential strategies for those ahead of the plan and those struggling to catch up. From refining your sales process to maximizing customer relationships, this discussion has insights to help you dominate your numbers in the coming months.

Key Topics Discussed:

The Reality of Q1 Performance and the Need for Urgency (00:00:31)
- Why waiting until Q2 to fix Q1 is too late, and how to position yourself for success early in the year.
Strategies for Those Ahead of Plan (00:01:00)
- How to maintain momentum, close key deals, and ensure a strong Q4 while staying ahead of quota.
Critical Steps for Those Behind on Quota (00:04:01)
- Conducting a win-loss analysis, diagnosing deal flow issues, and fine-tuning lead generation strategies.
The Importance of CRM Usage and Sales Efficiency (00:06:35)
- How sales leaders and reps can maximize their CRM to drive efficiency and uncover missed opportunities.
Pricing Strategies and Customer Engagement (00:09:13)
- Why now is the time to strengthen relationships with your top customers and confidently raise prices to improve margins?

Key Quotes:

Sean O’Shaughnessey (00:01:32): “You have a chance at greatness if you are even or ahead at the end of Q1. Now’s the time to double down and make sure you close deals that will set you up for an incredible year.”
Kevin Lawson (00:05:00): “Everyone has a leads problem. Either you don’t have enough, they’re not the right fit, or you’re not communicating your value effectively. That’s where the real focus should be.”
Sean O’Shaughnessey (00:11:00): “Your best customers likely don’t know you as well as you think. Strengthening those relationships can open up new revenue streams and prevent you from falling behind.”

A Significant Actionable Item from this Podcast:

Perform a rapid win-loss analysis on your Q1 deals. If you’re ahead, identify the behaviors and strategies that got you there and double down. If you’re behind, determine whether the issue is a lack of quality leads, poor messaging, or weak follow-through. Adjust your sales approach immediately so you can enter Q2 with a clear plan to recover lost ground.

Summary:

Whether you’re ahead of plan, right on track, or scrambling to catch up, the strategies discussed in this episode will help you refine your sales process and make Q2 a success. Sean and Kevin share actionable insights on deal flow, CRM optimization, pricing strategies, and customer engagement that will set you up for a strong year. Don’t let another quarter slip away—tune in now to get ahead, stay ahead, and finish the year on top!

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

Two Tall Guys Talking Sales – AI for Sales Success: Tools, Tactics, and Why You Can’t Ignore It – E124

By Sean O'Shaughnessey

Artificial intelligence (AI) is transforming the sales industry, but does that mean salespeople are becoming obsolete? Absolutely not! In this high-energy episode, Kevin and Sean debunk the myth that AI will replace sales professionals. Instead, they reveal how AI can be a game-changing tool for sales success.

From using AI to refine communication to automating time-consuming tasks, this episode is packed with insights on how AI can help sales leaders and reps work smarter, sell better, and stay ahead of the competition. Tune in to discover practical ways to leverage AI, improve efficiency, and dominate your market.

Key Topics Discussed

🔹 Will AI Replace Salespeople? – The truth about AI’s role in sales and why your job isn’t at risk—but your quota might be. (00:00:45)

🔹 The Evolution of Sales Tools – A nostalgic (and hilarious) look at how tools have always changed work processes—remember manual garage doors and TV dials? (00:02:21)

🔹 AI for Writing & Communication – How tools like Grammarly can make your emails, proposals, and presentations sharper, clearer, and more professional. (00:04:00)

🔹 Boosting Productivity with AI – From auto-generating customized sales presentations to intelligent scheduling, AI can free up time for what matters most: selling. (00:06:01)

🔹 The AI-Powered CRM – If your CRM doesn’t have AI integration or a plan for it, it’s time to rethink your strategy. A modern CRM is essential for competitive sales teams. (00:12:00)

Key Quotes

🗣️ Sean O’Shaughnessey: “You are not going to be replaced by AI. You’re going to be replaced by a salesperson using AI.” (00:01:00)

🗣️ Kevin Lawson: “AI isn’t here to take your job—it’s here to make you a better salesperson. Weaponize your tools and sharpen your axe.” (00:07:33)

🗣️ Sean O’Shaughnessey: “Being afraid of AI is like being afraid of Microsoft Word instead of a typewriter.” (00:10:18)

Additional Resources

🔗 Grammarly – AI-powered writing assistant for better emails, proposals, and reports.

🔗 Canva – AI-enhanced design tool for creating presentations and marketing materials in seconds.

A Significant Actionable Item from this Podcast

🚀 Start Using AI Today! Don’t wait—integrate AI into your daily sales routine now. Whether it’s improving your writing with Grammarly, using AI for scheduling, or leveraging AI-powered CRM features, pick one AI tool and start experimenting. The sooner you adopt AI, the further ahead you’ll be.

Final Thoughts

AI isn’t a threat—it’s an opportunity. The best salespeople will be the ones who embrace AI to work smarter, sell more efficiently, and build stronger customer relationships. Want to future-proof your sales career? It starts here.

👉 Hit play now and learn how AI can be your competitive advantage in sales!

Understanding Your Customers: The Role of Buyer Personas and Quarterly Business Reviews

By Sean O'Shaughnessey

Want to know the real secret behind successful sales? It’s not just about knowing what your customers need. The true power lies in understanding who they are at their core.

Have you ever wondered why some sales professionals consistently outperform their peers? The answer often comes down to their mastery of buyer personas and detailed profiles that capture the essence of your ideal customers.

Think of buyer personas as your secret weapon in the sales battlefield. These aren’t just random customer profiles thrown together in a rushed afternoon meeting. They represent carefully crafted composites of your most valuable clients, built from real-world data and insights. Your company might need several of these personas, each targeting different market segments with laser precision.

Creating effective buyer personas demands more than just surface-level observation. Start with a thorough analysis of your business landscape. Examine your strengths and weaknesses. Map out the opportunities that excite you and the threats that keep you up at night. This foundation helps you understand exactly where you fit in your customers’ world.

What makes your top customers tick? The answer lies in meaningful conversations with your best clients. These discussions should dig deep into both quantitative and qualitative factors. Demographics tell part of the story – age, position, education, family status. But the real gold comes from understanding their motivations. Why did they choose you? What problems do you solve that keep them coming back?

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Turning Competition into Opportunity: A Guide for Success in Sales

By Sean O'Shaughnessey

Competition in B2B sales isn’t your enemy. It’s your greatest catalyst for growth and innovation in today’s dynamic market landscape. Have you considered how viewing competitors as opportunities rather than threats could transform your sales approach? Let me show you why this mindset shift matters for your bottom line.

Think beyond the obvious when identifying your competition. Your real rivals aren’t just companies selling similar products or services. They’re anyone competing for your prospect’s budget allocation. This includes businesses offering solutions with capabilities or price points different from yours and other priorities within the prospect. The competitive landscape extends far beyond your direct market segment.

The most formidable opponent often lurks in the shadows of customer inertia. This “no-decision” competitor manifests as your prospect’s resistance to change. It’s the comfort zone that whispers, “Maybe later,” or “What we have works fine.” Understanding this psychological barrier is crucial for your sales strategy.

You need a systematic approach to analyzing and outmaneuvering your competition. Start with an honest assessment of your position in the market. What unique value do you bring to your customers? Where do you consistently outperform others? This self-awareness forms the foundation of your competitive strategy.

Know your competition inside and out. Study their strengths, weaknesses, market positioning, and customer relationships. Your competitive analysis must go deeper than surface-level observations. Map out how their strengths align with your weaknesses. This intelligence helps you craft more compelling value propositions and sales approaches.

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Balancing Act: Networking, Direct Prospecting, and Customer Referrals for Revenue Growth

By Sean O'Shaughnessey

Is your sales pipeline running dry? We’ve all been there.

Let me share a personal story that might resonate with you. After spending months securing a major deal, I found myself staring at an empty pipeline. The celebration of landing that giant whale quickly became a stark reality check. This experience taught me an invaluable lesson about sustainable sales growth.

Revenue generation isn’t just about closing deals—it’s about maintaining a consistent flow of opportunities. Your success depends on mastering the art of prospecting, yet many salespeople struggle with this fundamental skill. Are you dedicating enough time to building your pipeline, or are you caught in the feast-and-famine cycle?

The most effective sales professionals understand that prospecting isn’t a one-dimensional activity. Think of your prospecting strategy as a carefully orchestrated symphony, where different elements work together to create a harmonious result. Direct outreach and network-based approaches each play their unique roles in this composition.

Visualize a three-legged stool symbolizing the three-pronged approach to sales: networking and referrals, direct prospecting, and existing customers. Each of these legs supports growing your business and consistently achieving your revenue goals.

Consider how a software company might approach this dual strategy. While tracking metrics for direct outreach is straightforward, measuring networking success requires a different lens. How many new relationships have you cultivated? Which dormant connections have you rekindled? These indicators matter just as much as your cold call statistics.

I recently spoke with a consulting professional who shared an interesting perspective on networking metrics. Rather than counting sales pitches, he measures success by the number of times he naturally introduces his services in conversations. This subtle shift transforms aggressive selling into educational opportunities. Have you considered how this approach might work in your context?

Your prospecting strategy must align with your target audience’s expectations and behaviors. Waiting for inbound leads isn’t a strategy—it’s a recipe for inconsistent results. When you prospect through your network, the goal isn’t to ask for immediate business. Instead, you’re planting seeds for future opportunities through strategic introductions.

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Selling Trust: The New Era of Salesmanship in the Digital Age

By Sean O'Shaughnessey

Have you ever wondered why some salespeople consistently outperform their peers? The answer might surprise you – it’s not about pushing products anymore. Let me share a story that perfectly illustrates this point.

Picture yourself at a car dealership with a problematic engine. The service manager listens briefly and suggests trying premium fuel first instead of pushing for expensive repairs. This unexpected advice reveals the essence of modern sales: building trust over making quick profits.

The digital revolution has transformed how we sell. Your prospects now have instant access to product information, specifications, and reviews. They’ve often completed 70% of their buying journey before contacting you. So, what’s your role in this new landscape?

You must evolve from an information provider to a value creator. Think about it – when did a customer last ask you for basic product details? They don’t need that anymore. They need someone who can help them navigate complex decisions and create innovative solutions.

Consider enterprise software sales. Your customers aren’t just buying features and functions. They’re investing in solutions to their business challenges. Can you help them visualize how your product transforms their operations? Do you understand their workflow well enough to spot opportunities they might have missed?

Trust becomes your most powerful differentiator in this environment. But how do you build it? Through actions, not words. When you genuinely prioritize customer success over immediate sales, people notice. They remember when you steered them away from unnecessary purchases or suggested more cost-effective solutions.

The modern sales process demands a deeper understanding of your customer’s business context. You’re not just matching products to needs – you’re helping define those needs. What problems keep your prospects awake at night? Which industry trends threaten their market position? How can your solution help them stay competitive?

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