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Hiring for Growth: How to Build a Sales Team That Drives Long-Term Success

By Sean O'Shaughnessey

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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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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Turning Around Sales Performance: Strategies for CEOs and Sales Managers to Foster Internal Alignment

By Sean O'Shaughnessey

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.

The process starts with a shift in mindset.

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.

Are you trying to double revenue in 12 months?
Or just return to last year’s baseline?
Is that goal realistic given your market, team, and resources?

If not, revise it. A stretch goal is fine. A fantasy is not.

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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.

How to Create an Elevator Pitch That Opens Doors

By Sean O'Shaughnessey

Seize the Moment—Even If It’s Only 30 Seconds

You’re at a networking event. Or in line at the airport. Or maybe, quite literally, in an elevator. Someone turns to you and asks, “So, what do you do?”

That question—simple as it is—can be the beginning of a great opportunity… or a missed one.

As a small company fighting for attention in a crowded market, you don’t have the luxury of wasting that moment. You need a clear, concise, and compelling elevator pitch to earn a second conversation.

The Purpose of an Elevator Pitch

Your elevator pitch—or Unique Selling Proposition (USP)—is your verbal business card. It should quickly communicate what you do in a way that intrigues the listener and invites them to want more.

Your goal isn’t to close a deal on the spot. It’s to spark curiosity. It’s to turn a casual chat into a qualified lead.

The Anatomy of an Effective Elevator Pitch

Let’s break down what makes a pitch effective—and memorable.

1. Start with a Clear, Impactful Statement

Skip the jargon. Skip your job title. Lead with value.

“I help company owners dramatically increase the market value of their company.”

That kind of opener gets attention. It invites the natural question: “How do you do that?”

2. Avoid the “AND” Trap

Trying to cram too much into your pitch dilutes your message. Avoid saying, “We do this AND that AND also this.”
Instead, focus on one powerful value proposition. If you confuse your listener, you’ll lose them.

3. Know Your Audience

Adapt your pitch to fit the moment and the person. You wouldn’t speak to a private equity investor the same way you would to a small business owner. Tailor your language, examples, and tone to resonate with the listener.

Use a Mini Case Study with the PONI Method

If you have 10 more seconds of their attention, use it to share a brief, compelling client success story using the PONI method:

Project: What challenge did your client face or what were they trying to accomplish?
Old: How did they do that before?
New: What did you provide that changed things?
Impact: What was the measurable result?

“One of my clients leveraged increased revenue to grow their company’s market value by 167% in just 10 months.”

That’s the kind of story that gets remembered.

Don’t Forget the Ask

Close by inviting the next step:

“I’d love to share how we did it—can we schedule a follow-up conversation?”

That one line can turn a random encounter into a real opportunity.

Watch the Video

To see these concepts in action and learn how to craft your own elevator pitch, watch this short, practical video:

Want Help Refining Your Elevator Pitch?

If you’re ready to sharpen your messaging and make every introduction count, I’m happy to help.
Email me at Sean at NewSales dot Expert or send me a message here.

Let’s turn your next chance meeting into a business breakthrough.

The Power of Personal Branding in Enhancing Sales Productivity

By Sean O'Shaughnessey

Navigating the world of sales can sometimes feel like traversing a labyrinth. Salespeople, sales managers, and CEOs alike grapple with the challenge of increasing revenue and enhancing productivity in their sales processes. To be successful, you need more than knowledge of products and services; you need to develop trust and a strong personal brand.

Business-to-business (B2B) sales involves transferring trust from ourselves to our prospects. We trust in our products and company, but convincing prospects to share that trust is the real challenge. This trust should encompass the product, the company, and perhaps most crucially, the salesperson. Remember, B2B sales could be defined as helping prospects decide in our favor within the desired timeframe.

The key to B2B sales is developing a personal brand that inspires trust in salespeople. The salesperson’s ability to convey reliability, expertise, and credibility can significantly influence how fast a prospect invests in a product or service.

Developing a strong personal brand begins with creating a presence that signals control and understanding of the business. This can be achieved by showcasing the benefits of your product or service to your customer’s business. A straightforward way to build your brand is by seeking references from your network, former employers, and customers, and showcasing these on professional platforms like LinkedIn.

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Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

By Sean O'Shaughnessey

Welcome back to another episode of Two Tall Guys Talking Sales with Kevin Lawson and Sean O’Shaughnessey! This week, we’re diving deep into measuring marketing effectiveness with special guest Amy Connor, founder of CMO OnLoan. If you’ve ever struggled to connect marketing strategies to real business results, this episode is for you. Grab your marketing colleague and tune in—understanding what’s working (and what’s not) in your marketing is the key to driving sales growth.

Key Topics Discussed:

The Importance of Measuring Marketing Performance (01:08)
Many companies don’t effectively track their marketing impact. Amy shares how focusing on key metrics—without overwhelming dashboards—can create a direct path to success.
Sales and Marketing Must Be Aligned (02:09)
Customers don’t see marketing and sales as separate—they see one company. Amy explains why integrating both functions is crucial for a seamless customer journey.
Why Vanity Metrics Don’t Matter (02:55)
Impressions, clicks, and leads may look impressive, but if they don’t translate to business results, they don’t matter. Learn how to focus on meaningful data that connects to revenue.
The Billboard Advertising Myth (03:12)
Can a billboard drive B2B sales? Amy and Sean discuss the realities of traditional advertising and why small businesses should think critically about marketing spend.
Aligning Sales Messaging with Marketing Content (05:57)
Sales teams shouldn’t be the only ones communicating key messages. Amy shares why marketing content must reinforce what salespeople say to build trust and shorten sales cycles.
Tactical vs. Strategic Marketing – What’s the Right Balance? (08:29)
Should your marketing focus on brand awareness or immediate sales action? Amy explains the difference and how to measure each effectively.

Key Quotes:

Amy Connor: “Marketing and sales are part of the customer’s journey in a united way. The customer doesn’t see ‘marketing did this and sales did that’—they see the company as a whole.” (01:45)

Sean O’Shaughnessey: “Salespeople start at a disadvantage because buyers inherently don’t trust them. That’s why marketing must reinforce their message to build credibility.” (05:40)

Kevin Lawson: “Up to 70% of the buyer’s journey happens before they talk to sales. If marketing isn’t working ahead of time, you’re already losing.” (07:52)

Additional Resources:

Visit CMO OnLoan for free marketing resources: www.cmo-onloan.com
Connect with Amy Connor on LinkedIn: Amy Connor LinkedIn
Listen to the first episode featuring Amy: Last Week’s Podcast: https://podcasts.apple.com/us/podcast/amy-connor-discusses-salespeople-vs-lead-generation/id1668686029?i=1000693738159

A Significant Actionable Item from this Podcast:

Audit Your Marketing Metrics
Take 30 minutes this week to assess what marketing data your company is tracking. Are you focusing on impressions and clicks or lead conversion and revenue impact? Identify one metric that directly connects marketing activity to business growth and make it your priority.

Why You Should Listen to This Episode

Marketing is more than just branding—it’s a revenue-driving function. In this conversation, Amy Connor unpacks how B2B companies can measure what truly matters, align sales and marketing, and ensure every dollar spent on marketing contributes to the bottom line. If you want your marketing efforts to drive real sales results, don’t miss this insightful discussion. Tune in now!

Two Tall Guys Talking Sales – Amy Connor discusses Salespeople vs. Lead Generation: Are You Using Your Team Wisely? – E125

By Sean O'Shaughnessey

How do you measure the success of your sales and marketing efforts? If you’ve ever wondered whether your marketing dollars are driving revenue or if your sales team is making the most of their leads, this episode is for you.

Kevin Lawson and Sean O’Shaughnessey sit down with Amy Connor, founder of CMO on Loan, to discuss how marketing and sales should work together for growth. Amy brings her extensive experience from Procter & Gamble, Luxottica, and other top brands to help mid-market companies build marketing confidence, align with sales, and drive measurable results.

Key Topics Discussed

The Basketball Analogy: Why Tracking Performance Matters (~00:01:00)
- Just like basketball teams analyze stats post-game, businesses need to measure marketing and sales effectiveness.
How to Decide Between Investing in Sales or Marketing (~00:04:30)
- Business owners often wonder whether they should put more resources into sales teams or marketing initiatives—Amy breaks it down.
Aligning Marketing and Sales for Lead Generation (~00:07:30)
- Should salespeople generate their own leads, or is there a more efficient way to bring prospects to the table?
The Role of a Fractional CMO: How Businesses Can Engage Marketing Leadership (~00:11:20)
- Amy explains how a fractional CMO helps companies make smarter marketing decisions without the full-time executive cost.
A Sneak Peek into Next Week: Measuring Marketing Effectiveness (~00:13:52)
- Tune in next week as Amy shares the tools and strategies that help businesses track what’s working and what’s not.

Key Quotes

Sean O’Shaughnessey (~00:06:41):
“So many of my clients assume that salespeople will find their own leads, but is that really the best use of their time?”
Amy Connor (~00:07:51):
“Your sales team is often being asked to do too much. Something will suffer if they have to hunt for leads and nurture accounts at the same time.”
Kevin Lawson (~00:11:00):
“When companies say, ‘I need more sales,’ what they often mean is, ‘I need more leads.’ But are they solving the right problem?”

Additional Resources

Learn more about CMO on Loan and how they help businesses improve marketing effectiveness: www.cmo-onloan.com
Connect with Amy Connor on LinkedIn: https://www.linkedin.com/in/amyconnor/

A Significant Actionable Item from this Podcast

Evaluate your marketing and sales alignment. Take a step back and ask:

Do I have a clear process for tracking where leads come from and how they convert?
Is my sales team spending too much time prospecting instead of closing deals?
Would marketing support help my business generate higher-quality leads?

If you’re not sure, it may be time to review your funnel and define a strategy that ensures sales and marketing work together—not in silos.

Why You Should Listen to This Episode

This episode is a must-listen for business owners, sales leaders, and marketing professionals looking to make smarter investments in growth. Amy Connor shares real-world insights on how marketing can drive measurable business results and how sales and marketing can function as a united force. Plus, next week’s episode will dive even deeper into how to measure marketing effectiveness, so don’t miss it!

🎧 Download now and take the first step toward a more effective marketing and sales strategy!

Two Tall Guys Talking Sales Podcast – Activating Your Sales Ecosystem for Growth – E92

By Sean O'Shaughnessey

Join Kevin Lawson and Sean O’Shaughnessey in a compelling episode of “Two Tall Guys Talking Sales,” which delves into the power of networking and relationship management in sales. Whether you are a seasoned sales professional or just starting, this episode offers invaluable insights into maximizing your sales ecosystem without overwhelming your contacts.

Key Topics Discussed:

Activating Your Network [00:00:00]: Kevin highlights the importance of leveraging existing relationships and simple, actionable strategies to enhance your sales pipeline.
Realistic Relationship Management [00:01:36]: Sean discusses the practical aspects of maintaining a manageable network that can drive business growth.
Frequency of Contact [00:04:54]: Explore how often to engage with your network, including referral partners and past customers, without becoming a nuisance.
Digital Communication vs. Personal Interaction [00:06:00]: This section dissects the balance between digital outreach and personal connection to optimize relationship value.
Segmenting Contacts [00:08:29]: Sean shares his method of categorizing contacts into A, B, and C lists to tailor communication frequency and maintain effectiveness.

Read the rest of the article…

Two Tall Guys Talking Sales Podcast – Sales Mastery with Tom Daly: Transforming Newbies into Business Leaders – E80

By Sean O'Shaughnessey

Join hosts Kevin Lawson and Sean O’Shaughnessey on “Two Tall Guys Talking Sales” for another enriching episode, this time featuring the insightful Tom Daly from Focus Insights Group. Building on the momentum of our previous conversation in the last episode of Two Tall Guys Talking Sales, Tom delves deeper into the world of sales, sharing his expertise on nurturing new talent and guiding companies to refine their sales strategies for sustained success. Whether you’re a fledgling salesperson or a seasoned executive, Tom’s advice is bound to enlighten and inspire.

Key Topics Discussed

Transitioning from Pitch Person to Business Leader: Tom offers invaluable advice for new sales professionals on evolving from knowing just the features and benefits of their products to becoming strategic business advisors to their clients.
The Importance of a Structured Onboarding Program: Emphasizing the critical role of a meticulously planned onboarding process to ensure new salespeople are set up for success from day one.
Role of Sales Management in Nurturing New Talent: Discussion on how sales managers should not just be top sales producers but mentors who demonstrate, guide, and provide constructive feedback to their teams.
Building a Sales Strategy: Tom underlines the necessity for sales managers to have a clear, actionable sales strategy aligned with the company’s business plan to drive success.
Sales as a Business Management Function: Reinforcing the concept that effective sales management is synonymous with astute business management, focusing on strategic planning and execution.

Key Quotes

Tom Daley:

“You have to demonstrate. Then you have to do it. Then you have to have somebody try it, then you have to critique them and then you have to show them again and rinse and repeat.”

Sean O’Shaughnessey:

“I really try to teach my salespeople to think like a business person. It helps them a lot when they start to negotiate because now we can negotiate like a business person as opposed to a salesperson that wants a commission check.”

Kevin Lawson:

“Practice makes easy, not practice makes perfect. Practice makes easy because, man, I love your phrase. It’s an unnatural human behavior to start cold calling.”

Additional Resources

Sales Xceleration: Tom’s brand and passion, offering sales optimization services. – www.salesxceleration.com
Focus Insights Group, LLC: Learn more about Tom’s consultancy, which helps clients achieve their best sales year. – Focus Insights Group, LLC

Summary

This episode of “Two Tall Guys Talking Sales” with Tom Daly has been a deep dive into the art and science of building a successful sales career and managing a sales team effectively. Tom’s seasoned perspective sheds light on transitioning from being a pitch-focused salesperson to a strategic business advisor, offering actionable strategies for salespeople at every career stage. With a focus on the importance of structured onboarding, the critical role of sales management, and the development of a solid sales strategy, this conversation is a treasure trove for anyone looking to elevate their sales game.

If you’re a new salesperson looking to make your mark, a sales manager aiming to nurture your team, or a CEO striving for sales excellence, this episode is packed with wisdom you won’t want to miss. Download now and start transforming your sales approach today.