strategic sales

ChatGPT vs. Claude vs. Gemini vs. Copilot: Which AI Wins in Sales?

By Sean O'Shaughnessey

A few days ago, a sales manager asked me which AI platform to use for writing cold emails. I told him it depends on what kind of emails he’s writing, and he looked confused. That confusion is common and costly. ChatGPT, Claude, Gemini, and Copilot all look similar at first glance, but in reality, they serve very different purposes depending on your sales workflow.

Choosing the right platform matters because the wrong choice drains time, creates change fatigue, and erodes ROI. Companies that align platform strengths to sales use cases are seeing dramatic results: 40% higher email response rates, 60% faster proposal generation, and triple the efficiency in call preparation. The stakes are high, and the decision deserves more than guesswork.

ChatGPT: The Versatile Performer
ChatGPT shines when creativity and personality are critical. It’s excellent for cold emails with humor, social selling posts, objection-handling scripts, and meeting prep. The downside? It can be verbose and sometimes casual for executive communication. If your team thrives on creativity and prospecting with personality, ChatGPT is a strong choice.

Claude: The Professional Communicator
Claude specializes in polished, business-appropriate communication. It’s strong for executive proposals, deal analysis, contract prep, and professional email sequences. While less creative than ChatGPT, it’s ideal for enterprise and strategic sales where tone, nuance, and professionalism are paramount.

Gemini: The Integrated Researcher
Google’s Gemini offers real-time research, market intelligence, and smooth integration with Google Workspace. It’s especially powerful for sales teams who rely heavily on spreadsheets, Gmail, and real-time prospect research. However, it may produce generic copy and come with potential data privacy concerns.

Copilot: The Enterprise Integrator
Microsoft Copilot excels in environments already standardized on Microsoft tools. Its strength lies in Outlook automation, PowerPoint proposals, Teams prep, and CRM integrations. While it can feel corporate and less creative, it’s perfect for organizations that value compliance, governance, and seamless integration across Microsoft 365.

Making the Right Choice
The best AI platform isn’t the one with the flashiest marketing; it’s the one your team will consistently use. Start by mapping your use cases: creative outreach, professional communication, research, or enterprise integration. Then run pilot programs, measure results, and refine your approach. Many sales teams find value in using more than one platform, each aligned to a different stage of the sales cycle.

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 Tool for Sales Pros on your favorite podcast player.

Two Tall Guys Talking Sales – John McLeod Explains How to Avoid the AI Trap: Using New Tools Without Losing Your Sales Message – Episode 140

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey are joined by veteran fractional VP of Sales, John McLeod. Together, they dive into a critical topic for today’s sales leaders: embracing artificial intelligence tools without compromising your value proposition, messaging, or sales processes. John brings deep expertise in sales management, business acumen, and revenue generation strategies, offering a measured approach to evaluating sales tech, especially AI solutions, through a risk-and-reward lens. Whether you’re a business owner, sales manager, or BDR excited about AI, this conversation grounds you in practical wisdom.

Key Topics Discussed

The Real Risk of AI in Sales (00:01:22): How overreliance on untrained AI tools can misrepresent your brand and do more harm than good.
Sales Productivity vs. Organizational Efficiency (00:02:01): Why the focus shouldn’t just be on doing more faster, but also on syncing with your company’s value selling model
Three Essential AI Use Cases in Sales (00:03:25): Research, qualification, and outreach—and why each comes with its own operational risk.
The Ethical Use of AI and Messaging Integrity (00:07:43): Why maintaining consistent messaging across AI-enabled tools is essential to preserving brand integrity and revenue management.
Training AI for Sales Value (00:10:00): How smart prompt engineering and structured inputs drive better outcomes from generative AI tools.

Key Quotes

John McLeod (00:05:27):
“AI tools are meant to be trained. The biggest risk is: are they in fact supporting your unique and distinctive value proposition and holding true to that?”
Sean O’Shaughnessey (00:11:38):
“You won’t lose your job to AI—but you might lose it to another salesperson who knows how to use AI more effectively.”
Kevin Lawson (00:09:40):
“When you introduce AI and efficiency, that naturally raises the bar of expectation for performance. What is the new normal when you get there?”

Additional Resources

John McLeod’s LinkedIn Profile – https://www.linkedin.com/in/johnmcleod1/

A Significant Actionable Item from this Podcast

Train Your AI with Purpose: Don’t just “plug and play” AI tools. Take the time to structure your inputs and refine your prompts so that the tool reflects your value, not just generic sales content. Spend time A/B testing different approaches to ensure messaging aligns with your company’s strategic sales positioning. Start today by reviewing your most recent outreach generated by AI and ask: “Does this truly represent our value?” If not, retrain your prompts before using them again.

Why You Should Listen Now

If you’ve ever been tempted by the next great sales tool or AI platform promising instant leads and effortless sales success, this episode will recalibrate your thinking. John McLeod delivers candid insights on balancing tech adoption with strategic discipline. With Sean and Kevin steering the conversation, this discussion is rich with real-world experience in sales management, messaging, and revenue generation. Tune in now to stay ahead without losing what makes your company valuable.

Two Tall Guys Talking Sales – Steve Caton Shares When to Sell, When to Coach, and When to Hire: Strategic Sales Management That Drives Growth – Episode 137

By Sean O'Shaughnessey

In this powerful episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey are joined once again by Steve Caton, CEO of Altezza Solutions, for a thought-provoking conversation that zeroes in on one of the toughest decisions in sales leadership: when to sell, when to coach, and when to hire. Whether you’re a business owner, VP of Sales, or a player-coach juggling a quota and a team, this episode brings clarity to the strategic inflection point where growth hinges on letting go. With frank discussion, lived experience, and tactical advice, Kevin, Sean, and Steve guide you through the complex terrain of sales management, revenue generation, and scaling your team without sacrificing results.

Key Topics Discussed:

[00:01:58] The pros and cons of player-coach sales roles, and why this model often fails without intentional strategy
[00:05:34] How to create a psychologically safe sales environment where learning from failure drives sales success
[00:07:11] Steve Caton’s personal transition from sales operator to CEO—and how it triggered exponential business growth
[00:09:20] The difference between hiring to “swim faster” and hiring to scale—how business acumen guides the decision
[00:13:00] Real-world use cases for fractional sales roles to test new markets or offerings without disrupting core revenue streams

Key Quotes:

Kevin Lawson [00:04:57]: “Sometimes you have to let people fail. You can’t push them into failure, but you do have to give them the room to learn. The challenge is, as a leader, you’re still accountable for that failure.”
Sean O’Shaughnessey [00:04:01]: “It’s much easier to do one thing well. Let great salespeople sell and great managers manage—don’t dilute either role.”
Steve Caton [00:08:30]: “I made the decision to stop selling before I could afford it. Why? Because I knew the payoff would be big. Sometimes, you just have to invest in your business to grow.”
Kevin Lawson [00:11:34]: “A sales process with control metrics, plus intentional feedback loops, informs exactly how and where your business should grow.”

Additional Resources:

Steve Caton https://www.linkedin.com/in/scaton/
Altezza Solutions: www.atezzasolutions.com
Book Mentioned: Great by Choice by Jim Collins (for the “bullets before cannonballs” strategy) https://a.co/d/1j6R6vt

A Significant Actionable Item from this Podcast:

Reevaluate your team structure and decide: are you scaling or surviving?
If you’re a business owner or sales leader wearing multiple hats, it’s time to assess whether you’re enabling growth or capping it. Consider where your time is most valuable—rainmaking, coaching, or closing—and invest in building the right team around you. Start with fractional or part-time hires to test new roles or markets, then double down when the data supports it.

Closing Summary:

This episode cuts through the noise around sales team building with a refreshing mix of vulnerability, experience, and strategic depth. Whether you’re weighing your first sales hire or deciding to step out of the player-coach role, Two Tall Guys Talking Sales delivers real-world sales strategies that help you align your messaging, sales processes, and revenue management decisions with long-term growth. Don’t miss this one—it’s 15 minutes of business-building insight that could change the trajectory of your sales organization. Hit play now and discover how letting go might be the smartest way to grow.

Stop Guessing. Start Assessing: The First Step Toward Sales Growth

By Sean O'Shaughnessey

Are you feeling stuck in your sales organization? You’re not alone. Many founders, CEOs, and sales leaders eventually hit an invisible wall—a growth plateau. Key deals slip away. Your top salesperson, who carries far too much weight, starts to burn out.

In these moments, the instinct is often to push harder. But what’s needed isn’t more hustle. It’s clarity. And clarity starts with a strategic sales assessment.

What a Sales Assessment Means

Too often, leaders see assessments as formalities—checklists that confirm what they already believe. That’s a mistake. An accurate sales assessment is diagnostic. It reveals what’s working, what’s broken, and what’s missing.

Revenue growth doesn’t always mean you’re on the right path. Many companies are growing despite misalignment, not because of strategic execution. Are your sales activities aligned with your market opportunity? Are you pursuing the right prospects with the right message? Or are you just getting lucky?

Read the rest of the article…

Stop Guessing, Start Growing: How Strategic Sales Assessments Drive Real Revenue

By Sean O'Shaughnessey

You’ll eventually hit a wall if you’re running a sales organization—or wearing multiple hats as founder, CEO, and sales manager. That wall is often invisible until growth stalls, key deals slip through the cracks, or your top salesperson burns out. So, what’s the next move? It’s not more hustle. It’s assessment.

A sales assessment isn’t about checking boxes. It’s about understanding where you are, how you operate, and what’s holding you back. Too many small business leaders assume they’re doing fine because revenue is growing or the team is hitting their quotas. But are you growing at the rate your market allows? Are your sales activities aligned with your long-term goals? Are you building a repeatable system, or are you just getting lucky?

Let’s get tactical. A sales plan isn’t just a revenue target. It’s your go-to-market strategy. It defines your audience, your message, and your motion. It answers why you’re talking to those prospects and what value you’re bringing to them. Without a plan, you’re reacting instead of executing. You’re chasing leads instead of building a pipeline.

If you’re a small company—perhaps under $30 million in revenue—and selling into a national market, chances are your market potential is hundreds of millions, maybe billions. That means your market share is a rounding error, which means there’s room to grow. The question is: Are you operating in a way that allows you to capture that growth?

Even if you’re running lean, you should benchmark your performance against top-tier organizations. Not because you’re competing with them directly, but because they set the standard. What are they doing that you’re not? Where are they more efficient? How do they structure their teams? You’re leaving money on the table if you’re not asking those questions.

Read the rest of the article…

Roadblocks, Detours, and Destinations: The Intricate Art of Sales Strategy

By Sean O'Shaughnessey

There’s an ongoing conversation about the importance of strategy, process, and anticipating potential challenges in B2B sales. There’s an analogy that encapsulates this perfectly – imagine you’re on a road trip. You have a destination in mind but are unfamiliar with the route. This is where tools like Waze, Google Maps, or Apple Maps come into play. They direct you to your destination and alert you about potential roadblocks, construction, traffic, or other unexpected events that might delay your journey.

This is precisely how a sales strategy should work. It’s not just about getting from point A to point B but also about understanding the complexities of the journey and preparing for potential roadblocks. For salespeople, managers, and CEOs, understanding the strategy is critical to increasing revenue and improving productivity.

Understanding that a strategy involves more than just the turns along the way is vital. It also involves how to navigate through different areas, understand the speed limit, and anticipate any warnings that might come up. Many salespeople don’t fully grasp these challenges and tend to take them as they come rather than anticipating them and planning accordingly.

Like Waze uses real-time data to adapt to changes on the road, a sales strategy should adjust to new information and circumstances. For example, if there’s construction up ahead or a detour is required, Waze will adapt and provide a new route. Similarly, salespeople should be able to adjust their strategies based on new information or unexpected challenges.

Read the rest of the article…

The Right Person in the Right Seat: Unleashing Company Growth through Strategic Sales Leadership

By Sean O'Shaughnessey

A recurring issue for small companies has emerged; the company’s owner or CEO often leads the sales department. This might be because they believe no one else can sell their product or service better than they can. However, this mindset might be hampering the company’s growth potential.

If you’re a company owner or CEO who leads sales, it’s crucial to consider the risk of this approach. When the person leading the company also heads sales, the business is constrained by the amount of time that leader has. If your salespeople consistently wait for your input or response, you might face a growth opportunity and a challenge simultaneously.

The solution lies in de-risking your organization’s growth potential by getting a sales leader in the sales leadership seat separate from you. This concept resonates with the theory of constraints, a principle often applied in the manufacturing industry but equally applicable in sales. The theory of constraints focuses on identifying the factors that limit your success.

Read the rest of the article…

Focused Marketing Strategies: Driving Revenue with Account-Based Marketing

By Sean O'Shaughnessey

One strategy that stands out for its targeted approach and efficacy in business-to-business sales is account-based marketing (ABM). This approach aligns marketing and sales teams to concentrate on specific, high-value accounts, ensuring tailored interactions that increase the likelihood of conversion. For salespeople, sales managers, and CEOs of small companies, understanding and implementing ABM can be pivotal in driving revenue and achieving substantial business growth.

ABM centers on the identification and engagement of key accounts that are strategic to a business. Unlike broad-spectrum marketing strategies, ABM requires a deep understanding of the target company’s industry, structure, and business needs. This insight allows for a highly personalized approach in communications and offerings, fostering a closer relationship and higher engagement levels.

Effective implementation of ABM involves collaboration between sales and marketing teams to map out key information about an account, such as company size, industry specifics, and geographic locations. This collaborative effort ensures that both teams are aligned in their approach and objectives, enhancing the effectiveness of the marketing efforts.

Moreover, understanding the triggers and events within the target industry can provide opportunities for timely and relevant engagements. Customizing presentations and marketing materials to reflect the current industry landscape or the account’s specific challenges can significantly increase relevance and impact.

An interesting application of ABM is the development of dedicated landing pages or portals for major clients. This creates a personalized experience for key accounts, providing them with content tailored to their specific needs and interests, often resulting in increased customer satisfaction and loyalty.

Leadership involvement in ABM is also critical, often requiring significant investment and strategic focus. Deciding which accounts to target and ensuring that resources are appropriately allocated can distinguish between a successful ABM strategy and a costly misstep.

Moreover, ABM’s technology and tools must be carefully chosen and effectively utilized to reach and engage key accounts. This might include creating customized content such as videos, detailed case studies, and specially designed presentations that feature the prospective client’s logo and tailored messages.

For small companies, the challenge often lies in resource allocation. However, even limited resources can effectively create impactful ABM strategies. For instance, small-scale, personalized video messages can make a significant impression on potential clients, offering a personalized touch that can set a company apart from its competitors.

While ABM can be resource-intensive, its focused approach can yield significantly higher returns than traditional marketing strategies. For companies aiming to scale their operations and increase their market share, especially in competitive industries, ABM provides a strategic method to effectively target and win over key accounts. CEOs and sales leaders should consider how ABM can be integrated into their sales strategies to enhance their marketing efforts and drive business growth.

Here are several immediate actions that a sales leader can take today to implement Account Based Marketing effectively:

Identify Key Accounts: Review your current client list and select a handful of high-value accounts with the potential for deeper engagement and increased revenue. Use criteria such as current revenue, growth potential, strategic importance, and alignment with your business capabilities.
Align Sales and Marketing Teams: Organize a meeting with your sales and marketing teams to discuss the selected key accounts. Ensure everyone understands the importance of a unified approach and collaborates to map out each account’s specific needs and business landscape.
Develop Customized Content: Start creating tailored content that addresses each key account’s specific needs and challenges. This could include personalized emails, custom landing pages, and targeted case studies that speak directly to the account’s industry and objectives.
Set Clear Metrics and Goals: Define clear metrics and goals for tracking the success of your ABM efforts. This may include engagement rates, conversion rates, and, ultimately, revenue growth from key accounts. Regularly review these metrics to adjust strategies as needed for optimal performance.