Sales Planning

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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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.

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Two Tall Guys Talking Sales – Empowering Non-Sales Employees to Boost Customer Value – E109

By Sean O'Shaughnessey

In this episode, hosts Kevin Lawson and Sean O’Shaughnessey, take listeners on a journey to understand the power of non-sales roles in supporting a sales-centric culture. Expanding on prior discussions about sales planning and execution, they explore how professionals outside the sales department—think programmers, customer service reps, delivery drivers, and even truckers—can play a pivotal role in enhancing client satisfaction and identifying new opportunities. Kevin and Sean dive into practical steps sales leaders can take to foster a collaborative environment where everyone contributes to sales success, making this an unmissable episode for business leaders, sales professionals, and anyone looking to understand the value of cross-functional synergy in achieving enterprise growth.

Key Topics Discussed

The Sales Quadrant Framework [00:01:00]: Kevin and Sean introduce a framework for effective sales planning, dividing it into four quadrants: Strategy, Process, People, and KPIs. This framework guides leaders on fostering a holistic sales ecosystem.
Sales for Non-Salespeople: Defining the Role [00:01:40]: The hosts discuss how non-sales team members, from programmers to quality agents, can pass along valuable customer insights without selling directly. It’s about listening and relaying information to sales, not cold calls or quotas.
Leveraging Customer Interactions for Insight [00:03:14]: Sean shares a vivid example from his software background, where consultants gathering customer feedback created substantial upsell opportunities. He emphasizes the value of customer-facing team members in providing sales with a view from the trenches.
Building Relationships Across Teams [00:07:00]: Kevin discusses strategies to align cross-functional team goals with sales objectives, creating a supportive network that encourages the entire team to spot potential sales opportunities.
The Importance of Gratitude and Recognition [00:12:07]: Sean underscores the value of acknowledging and thanking team members who help sales, reinforcing their role in supporting company-wide goals and deepening relationships across departments.

Key Quotes

Kevin Lawson: “We’re not asking non-salespeople to sell, but we are asking them to raise their hand when they see something we might need to know about to help our customers better.” [00:01:59]
Sean O’Shaughnessey: “In every company, people need help achieving their goals. And often, the folks who see where we can help the most aren’t in the sales department—they’re on the front lines, interacting with customers daily.” [00:04:11]
Kevin Lawson: “Be a better person in business. Support your teammates, your vendors, and your community, and that support will circle back, lifting everyone’s success.” [00:14:04]
Sean O’Shaughnessey: “A simple ‘thank you’ can be the most valuable recognition, and it builds bridges with your team. Make it a habit.” [00:12:46]

A Significant Actionable Item from this Podcast

Empower Non-Sales Team Members to Listen for Opportunities
Sales leaders should hold short training sessions or casual discussions with non-sales staff, educating them on key signals that may indicate an opportunity. Encourage these team members to feel comfortable sharing insights with sales and clarify that they won’t be pressured to sell—just to observe and communicate.

Summary: This Two Tall Guys Talking Sales episode delivers essential insights for any sales-driven organization. Kevin and Sean emphasize the untapped potential within non-sales teams, showing how they can indirectly yet powerfully support sales efforts by sharing customer feedback and needs. With practical strategies for fostering collaboration and recognizing the contributions of non-sales staff, this episode is a must-listen for sales leaders looking to unlock every possible avenue of client satisfaction and revenue growth. Tune in and discover how even a small tweak in team communication can significantly impact your bottom line.

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

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey sit down with Richard Cogswell, a 20-year sales veteran and author who leads the APAC region in the FinTech space. Richard shares his journey from commission-only sales in the insurance industry to becoming a B2B sales leader in the complex world of payments. Together, they discuss the critical importance of developing a mission-led culture, the pitfalls of sales leadership without a plan, and actionable strategies for creating a structured sales environment.

Join the conversation as they explore how sales leaders can move beyond the typical financial-year focus and elevate their teams with clarity, focus, and purpose. Whether you’re a sales leader or a single contributor looking to up your game, this episode is packed with insights to help you build a more robust sales foundation.

Key Topics Discussed:

The Importance of a Go-to-Market Sales Plan (00:01:47): Richard highlights why many organizations lack an articulated sales strategy and the repercussions this can have on cross-functional alignment and growth.
From Surviving Year-to-Year to a Mission-Led Culture (00:04:22): The hosts dive into how sales leaders can shift from short-term financial targets to a long-term, mission-driven approach.
Creating a Structured Sales Environment (00:06:18): Richard explains the necessity of documenting your big bets and aligning your team with cross-functional partners.
Identifying and Empowering Sales Leaders (00:11:00): Learn how to recognize key players within your team and use them to foster growth and cohesion.
The Power of Salespeople Creating Their Own Plans (00:12:48): Richard shares the importance of involving sales reps in the planning process and how it strengthens accountability and execution.

Key Quotes:

Richard Cogswell: “If you’re a commercial leader and you don’t have a structured sales plan, I’m sorry, but that is your responsibility to create one. How else do you align your team and cross-functional leaders toward the same goals?” (00:03:18)
Sean O’Shaughnessey: “You have to have a plan. Kevin and I are often brought in as fractional VPs of sales, and the first thing we see is the absence of a plan, which is exactly why we’re needed.” (00:04:43)
Kevin Lawson: “I love what you said about getting beyond the fiscal year focus and building a mission-led culture. That’s a simple, but powerful, shift every sales leader needs to understand.” (00:10:31)

Additional Resources:

Richard Cogswell’s book, The Cultural Sales Leader: Sustaining People, Attaining Results, is available on Amazon, Barnes & Noble, and other retailers. https://a.co/d/1sc187j
Connect with Richard on LinkedIn for more insights into sales leadership and cultural transformation in business. https://www.linkedin.com/in/richardcogswell/

A Significant Actionable Item from this Podcast: Sales leaders should implement a one-page sales plan for their team. This document should clearly define the financial goals, top priorities, values and behaviors expected, and specific actions needed to achieve success. Ensure this plan is regularly revisited and adjusted to align with short-term and long-term goals.

Summary: In this episode, Richard Cogswell brings a wealth of experience to the table, sharing his journey from commission-only sales to leading an entire region in the FinTech industry. His insights into the necessity of structured sales plans, mission-led cultures, and empowering sales leaders are invaluable for anyone in sales leadership or aspiring to be. Whether you’re managing a team or just starting out, the principles Richard discusses can help take your sales strategy from surviving to thriving. Don’t miss this chance to learn how to build a focused, intentional sales culture that drives long-term success!