sales environment

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.

Read the rest of the article…

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.

Adapting to the New Sales Landscape: The Importance of Omni-Channel Outreach

By Sean O'Shaughnessey

Are you still relying on trade shows as your primary sales driver? The sales landscape has undergone a seismic shift. Those packed convention halls and endless rows of booths no longer serve as the bedrock of business development they once were.

Let’s talk about what works in today’s sales environment. Building an effective outbound pipeline isn’t just an option anymore – it’s your survival toolkit. But here’s the challenge: how do you stand out in a market where everyone’s fighting for attention?

Your unique value proposition makes all the difference. Yet many sales professionals miss a crucial point: your value proposition isn’t static. What resonates with a manufacturing client might fall flat with a distribution company. Have you tailored your message to address each industry’s pain points?

Think about your last prospecting campaign. Did you give up after four or five attempts? Research shows it takes 12 to 16 touches before prospects typically respond. This gap between persistence and practice often determines success or failure in modern sales.

The game has changed. Your prospects live in an omnichannel world. They check email between Zoom calls, scroll LinkedIn during lunch, and scan their phones throughout the day. How are you showing up in their digital world?

Consider this: every unanswered email or phone call might be a messaging problem. Are you talking about your features when you should be solving your prospects’ problems? Your prospects don’t care about your product specifications. They care about their challenges, their goals, and their bottom line.

Read the rest of the article…

Differentiating in the Sales Process: The Key to Boosting Bottom Line

By Sean O'Shaughnessey

The roles of salespeople, sales managers, and small business CEOs are ever-evolving. A common problem faced is increasing revenue and productivity in sales processes. This goal is common for all, from individual salespeople striving to provide for their families to CEOs seeking to boost their company’s bottom line. The key to achieving this lies in understanding the dynamic nature of the sales environment and leveraging it effectively.

A significant part of the sales process revolves around the buyer’s perception of a product or service as a commodity. This misclassification is usually caused by insufficient differentiation in the early stages of the sales process. Differentiation is crucial in any sales process, regardless of the industry or scenario. Creating enough differentiation can be the difference between closing a deal at a discounted rate or the desired price.

Salespeople are experts in their field, whether selling a unique product specific to their company or a common commodity. They typically have a deeper understanding of what they are selling than their prospects have about what they are buying. This expertise should be leveraged to guide prospects through the buying process, adding value to the relationship and making the salesperson indispensable. This approach can reduce the emphasis on price and increase the potential for higher earnings.

Every business has unique values that differentiate it from its competitors. These unique values could be anything from their mission, vision, and values to their market commitment and guarantee. This is commonly called a Unique Value Proposition (UVP) or a Unique Sales Proposition (USP). While a UVP and a USP are similar, there is a slight difference in that the former is typically created by the Marketing department (or sometimes with the help of a business adviser such as an EOS implementer. The latter is directly targeted at salespeople and what a salesperson should say to their prospects and customers. Salespeople should understand what makes them different and communicate this effectively to their prospects. The ability to create separation and differentiate oneself is why people pay for a product or service.

Read the rest of the article…

Overcoming Ghosting and Other Modern Sales Challenges: A Proactive Approach

By Sean O'Shaughnessey

Many salespeople, sales managers, and company CEOs grapple with the unique problem of adapting their sales strategies to ever-changing market dynamics. This problem stems from an old-fashioned practice in which sales leaders tend to offer the same advice that made them successful when they were nascent salespeople. However, to remain competitive and productive, realizing that this traditional advice may no longer hold relevance in today’s sales world is crucial.

Let’s consider a sales leader who made his mark when the internet was still in its infancy, and email and mobile phones were not part of the sales process. If this sales leader continues to advise their team based on those past experiences, they will likely be setting them up for failure. Today, the sales world is no longer about physical gatekeepers but about navigating spam filters and phone blockers. The sales environment has evolved, and it’s time sales strategies do, too.

A typical issue salespeople face today is being ‘ghosted’ by potential clients. Ghosting, a relatively modern term, refers to the situation where the person you’re trying to reach is not returning your calls or emails. It’s a frustrating experience, but it also indicates a salesperson’s failure to be proactive and do the right things earlier in the sales cycle. Modern salespeople need to think ahead, plan better, and ensure they set up the next meeting before leaving the current one. This proactive approach can help prevent ghosting, keep the sales conversation going, and indicate progress.

Read the rest of the article…

Building a High-Performing Sales Team: The Benefits of Recognizing Effort and Results in Sales Meetings

By Sean O'Shaughnessey

Sales drives the engine of any B2B business. Enhancing sales strategies and management capabilities is crucial to success for salespeople, sales managers, and CEOs of small companies. One aspect of this involves rewarding effort and results during sales meetings. This practice motivates the sales team and encourages them to strive for better performance.

Salespeople are naturally competitive and driven, but they also appreciate recognition. While a paycheck is important, it’s also essential for salespeople to feel valued and appreciated for their efforts. This recognition can come in various forms, from verbal praise to tangible rewards. It’s important to remember that recognition should not be limited to monetary rewards. The simple act of acknowledging someone’s hard work and contributions can be incredibly motivating.

A sales meeting is an opportune moment to recognize and reward your sales team’s efforts. It’s not just about discussing targets and strategies; it’s also a chance to celebrate successes, however big or small. These meetings can be used as a platform to highlight the best practices and strategies employed by the team members, fostering a culture of learning and improvement.

Every salesperson has a unique approach and strategy. If nothing else, they experiment with different ways to share the benefits of their product or ask a particular discovery question. By sharing these individual successes or failures during meetings, sales teams can learn from each other, thus promoting a collaborative and supportive environment. The sales leader may prompt these discussions, but the actual learning comes from the experiences and strategies the salespeople share.

Read the rest of the article…

The Multifaceted Role of a CEO in a Sales-Driven Business Environment

By Sean O'Shaughnessey

In the business world, the role of a CEO extends beyond just leading the company. It involves taking responsibility for the sales environment, shaping the company culture, and setting the vision for the future. This is particularly important for small companies where the CEO may also be the primary salesperson or sales manager.

One of the critical responsibilities of a CEO in a sales environment is to address and resolve problems. When a client is dissatisfied, the CEO must apologize and take responsibility for the issue. This doesn’t mean placing blame but owning the problem and finding a solution. It is also essential to have a plan in place to prevent similar issues from recurring in the future.

In addition to problem-solving, a CEO plays a significant role in shaping the company’s culture. The company’s culture should reflect the core values that the CEO and the team believe in. These core values should guide the company’s actions and decisions. For example, suppose one of the company’s core values is extraordinary service. In that case, every team member, from the CEO to the junior account person, should strive to provide exceptional client service.

As a CEO, it is also important to be the company’s visionary. This includes setting goals and communicating these goals to the team. The vision should inspire and motivate the team to strive for excellence. It should also give a clear direction on where the company is headed and what it hopes to achieve.

Read the rest of the article…