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How To Build A Highly Successful Sales Team

July 18th, 2024

A strong, high-performance sales team is critical to a successful business. But what makes a sales team successful? What strategies can leaders use to create a highly successful sales team? To address these questions, Nick Smith, CEO and Founder of Sailes, weighs in on his thoughts.

Can you tell us the “backstory” about what brought you to this career path?

My career has had a lot of range, from sales leadership to political advertising and a lot of abstract selling to bring multiple groups together. I’ve always been interested in the intersection of business and labor. Before starting Sailes, and in addition to my sales roles, I was the co-host of a radio show called “Common Ground” in New York that focused on bridging the gap between business and labor.

I founded Sailes in 2018 after spending the majority of my career in strategic sales at CBS Corporation, iHeartRadio, Audacy, and other companies. Through my time in Sales Leadership and Sales Management, I began to see how practical uses of AI could help human executives thrive by reducing repetitive manual tasks, increasing business development opportunities and multiplying output.

What is the most interesting or amusing story that has occurred to you in your career so far? Can you share the lesson or takeaway you took from that story?

In my career, the most interesting story revolves around the inception of Sailes. It all began on July 4th, 2018, at the Lake of the Ozarks in Missouri. I had a moment of inspiration that salespeople should have their own AI Sales Robot “Sailebot” that could automate prospecting tasks, allowing them to focus more on selling. I vividly remember jotting down this idea in my phone. The lesson I took from this is that great ideas can strike at any moment, even on a holiday, and it’s essential to act on them. Sometimes, those ideas can lead to transformative innovations.

Are you working on any exciting new projects now? How do you think that will help people?

Well, we actually launched our immersive user dashboard, Starboard™, just a few months ago. We’ve given our clients visibility and are slowly giving them more and more control of their AI with Starboard™. We’re not trying to simply “get AI in the hands of salespeople ” but allowing them to mold and modify their AI, which is extremely new and exciting.

Today our customers – usually a senior sales leader – can oversee all activity for their fleet of Sailebots and salespeople can onboard, instruct, deploy, and train their Sailebot®. They can see in real time what their Sailebot is working on, who they’re in conversation with, and make adjustments where necessary.

Can you tell us a bit about your experience leading sales teams? How many years of experience do you have, and what size teams have you worked with?

I have had extensive experience leading sales teams. Over the years, I’ve accumulated several years of experience in Sales Leadership and Sales Management. I’ve had the privilege of working with sales teams of varying sizes, ranging from smaller, more intimate teams to larger, more complex ones. This diversity in experience has provided valuable insights into what makes a sales team successful. 

What do you think makes a sales team great? What strengths or characteristics do you try to cultivate?

A great sales team is built on a foundation of trust, collaboration, and a shared commitment to success. I believe in cultivating a culture of continuous improvement, where team members are encouraged to enhance their skills and adapt to evolving market conditions. Effective communication, adaptability, and a customer-centric approach are crucial strengths I aim to cultivate within my team.

In your experience, what role does effective communication play in building a successful sales team? Can you share any techniques you’ve used to improve communication within your teams?

Effective communication is the backbone of a successful sales team. Clear and open communication ensures that team members are aligned with the organization’s goals and strategies. To improve communication, I’ve implemented regular All Hands team meetings, one-on-one check-ins, and use technology tools like Slack and JIRA. These practices promote transparency, information sharing, and a sense of unity among team members.

How do you maintain a healthy balance between competition and collaboration among your sales team members? Can you share an example of when this balance led to improved team performance?

Balancing competition and collaboration is an art in sales. While healthy competition can drive individual excellence, collaboration fosters a team spirit. I’ve found that setting team goals alongside individual targets can strike this balance effectively. For example, when we instituted a Digital Labor™ sales competition, it resulted in remarkable performance improvements. The collaborative aspect pushed team members to help each other succeed, which ultimately benefited the entire team.

What role does ongoing sales training and professional development play in the success of a sales team? Can you recommend any specific resources or methods that you’ve found particularly effective?

Ongoing sales training and professional development are paramount. Sales is a dynamic field, and staying current with industry trends and techniques is crucial. I encourage my teams to attend industry conferences, workshops, and webinars. Additionally, leveraging online courses and resources from platforms like LinkedIn Learning and industry publications helps keep our skills sharp and our knowledge up to date.

How do you keep your sales team engaged and motivated, even during challenging times or market downturns? Can you share a story or example from your own experience?

Maintaining team motivation during challenging times is essential. One effective approach is to celebrate small victories and milestones, even in the face of adversity. I remember a time when our sales team faced a particularly tough market downturn. To keep spirits high, we introduced a recognition program that acknowledged outstanding individual and team efforts in the form of email announcements. This recognition boosted morale and kept our team engaged and motivated.

What role does technology play in the success of a sales team? Are there any tools or platforms that you’ve found particularly useful for streamlining processes, enhancing collaboration, or providing valuable insights?

Technology is a game-changer in the sales world. We’ve seen significant success by incorporating AI, like our very own patent-pending Sailebots, to automate prospecting tasks. Our Sailebots empower our sales team to work more efficiently and focus on higher IQ tasks such as closing deals.

How do you approach setting goals and measuring success for the sales team? What key performance indicators (KPIs) do you focus on, and how do you ensure they are aligned with the overall goals of the company?

Setting goals is a meticulous process. We define clear OKRs for our entire team, as well as Key performance indicators (KPIs) that we focus on include sales revenue, conversion rates, and customer retention. These KPIs are closely aligned with the overarching goals of the company (OKRs), ensuring that the sales team’s efforts are in sync with the organization’s broader mission.

What are the five things you need to build a highly successful sales team? Please share a story or example for each.

1 .Strong Leadership: A highly successful sales team needs strong leadership to guide and inspire them. I’ve seen the impact of this firsthand when I took on a new leadership role and set a clear vision for the team, which led to a significant boost in performance.

2 .Effective Training: Continuous training and development are vital. Once, we invested in a set routine of prospecting and objections meetings for our team, we saw improved results in product knowledge and a notable uptick in sales.

3 .Motivated and Engaged Team Members: Motivation and engagement are infectious. I remember a time when one team member’s enthusiasm and energy lifted the entire team’s spirit, resulting in increased sales.

4 .Adaptability and Innovation: The ability to adapt to changing market conditions and innovate is critical. During a competitive market shift, our team’s willingness to try new approaches, even unconventional ones, led to breakthrough success.

5 .Clear Sales Strategy: A highly successful sales team requires a well-defined sales strategy. I recall a time when our team revamped our strategy to focus on a specific market segment. This shift allowed us to tailor our approach and connect with clients more effectively, resulting in a substantial increase in sales.

If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

If I could inspire a movement, it would be one that harnesses the power of AI and technology to bridge the gap between labor and business, just as I explored on my radio show, “Common Ground.” This movement would aim to create equitable opportunities and empower individuals in the workforce while boosting business efficiency. The convergence of technology and human potential can lead to a brighter future for all, and I would be honored to inspire and lead such a movement.