From Solo to Success: How to Build a Legendary Sales Team and Take Your Business to the Next Level

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From Solo to Success: How to Build a Legendary Sales Team and Take Your Business to the Next Level

What’s better than the thrill of starting your very own business? 

There’s nothing quite like it, in my opinion. I’ll never forget the rush of making my first sale, the satisfaction of seeing my creative visions come to life, and the excitement of hiring a stellar team to pull it all together. 

If there’s something I’ve learned from running my own business, it’s that you can’t – you simply can not – go it alone, especially when it comes to closing deals and making sales. 

In my recent conversation with Kris Rudeegraap, founder of Sendoso, we discussed business from many different angles; I was eager to dig into his expertise in sales. 

More specifically, I wanted to learn about his process for building a sales team. What does he look for in a candidate? How many people does he need? Should there be a balance of skills or a collection of all-stars?

Let’s talk about it. 

When to Hire a Sales Team

As an entrepreneur, I know all too well how tempting it is to want to handle everything yourself, from sales to marketing to operations. You might feel like you’re the only one who understands the vision of your business. You’re the only one who can do these things right. 

In the early stages of your business, this might work. But not for long. 

There comes a point when you hit a wall and can no longer be a one-person show, especially in sales.

So, when do you know it's time to hire a sales team? 

Kris and I agree on the answer: as soon as possible.

If you're seeing consistent demand for your product and sales are taking up most of your time, it's time to start thinking about building a team. You can only do so much, and if you want to grow your business and scale up, you need a team behind you.

The sooner you add a team to help you with your sales, the sooner you will be able to focus on other areas of your business, helping you ensure that there are no blind spots and no part of your business starts lagging. 

Why a Sales Team is Essential

John C. Maxwell, author of The 21 Irrefutable Laws of Leadership, once wrote:

“If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.”

There comes a point where every entrepreneur – or at least every entrepreneur chasing significant success – needs to pass on some of the responsibility to new team members. 

Part of that is because one person can’t handle all the work, but other benefits come with building a sales team, too. 

  • Growth: With fresh perspectives and approaches, you can generate new leads, close bigger deals, and drive growth you would otherwise have missed. 

  • Free up your time: Having a sales team frees you to focus on other business areas, like product development, marketing, and operations. 

  • Strong brand ambassadors: As they interact with customers and potential clients, team members can share your company's values, mission, and vision. A great sales team can help establish and strengthen your brand reputation, leading to greater brand recognition, loyalty, and trust.

  • Competitive advantage: A well-trained and motivated sales team can help you differentiate your product or service from your competitors, showcase its unique value proposition, and ultimately win over more customers.

Building a well-rounded team can have an especially positive effect. One study of 1,700 businesses across eight countries found that companies with diverse management produced 19% more revenue

How to Build a Legendary Sales Team

So how do you do it? Well, I’d be lying if I said it was simple. There’s no magic formula or secret pool of otherworldly candidates waiting for your call. It’s going to take work. 

But there are ways to optimize the process. Here’s a five-step system that can move you in the right direction. 

Step 1: Define Your Sales Strategy

Defining your sales strategy is the first step in building a legendary sales team. This means identifying your target audience, understanding their pain points and needs, and developing a unique value proposition that sets you apart from the competition.

Your sales strategy should also include clear goals, metrics, and processes to measure and evaluate your team's performance. Ensuring your team is on the same page and aligned with your overall business strategy is vital. This way, everyone can work together and hustle towards the same goals. 

Step 2: Hire the Right People

For a long time, skill, experience, and education were the only things considered in recruiting. If you could do the job, had done it before, and went to the right school – you’re hired!

But that has changed dramatically. The new adage is “hire for attitude, train for skill.” Go ahead, search that phrase in Google right now and see how many results come up. I’ve written it in this newsletter many times and heard it on the Success Story podcast even more often. 

But let’s not just throw out rhetoric. What does it mean?

In my opinion, it’s all about communication. People don’t need to be best friends at work; they don’t need to have the same interests or hobbies. But they need to be able to effectively (and efficiently) communicate. 

So when you’re vetting potential team members, put them in situations where they need to explain a problem on the spot, devise a quick attack plan, or interpret confusing instructions. 

Ask them things like:

  • Could you explain a tricky idea or concept to a total beginner?

  • Tell us about when you had to adapt how you talk for someone else's understanding.

  • What's your approach to sharing helpful suggestions with a coworker?

  • What are your go-to strategies for bonding with new people in a work setting?

  • How would you handle a situation where someone on your team isn't doing their part? How would you get things back on track?

Don’t overlook their background completely, but sales isn’t rocket science. If you can communicate effectively, the rest of the job will come with some experience. 

Step 3: Train and Develop Your Team

If you hire that way, though, you better be ready to invest in growth. One survey from Zippia found that 87 percent of Millenials believe professional development is important, and more than two-thirds of all employees say training and development are the most critical company policies. 

Consider using role-playing exercises, shadowing opportunities, and regular team meetings to enhance your team's skills and promote collaboration. 

Mentoring programs have significant positive effects on both sides of the relationship – mentor and mentee – while employee education programs can help onboard and retain top talent. 

Step 4: Set Clear Expectations and Goals

Setting clear expectations and goals is essential to keeping your team focused and motivated. Make sure everyone on your team understands their roles and responsibilities and the metrics and targets they are expected to achieve. 

Explain and monitor key performance indicators (KPIs) like: 

  • Sales revenue

  • Conversion rate

  • Average deal size

  • Sales cycle duration

  • New customers acquired

Use regular performance reviews to track progress and provide feedback. By setting clear expectations and goals, you'll be able to hold your team accountable and ensure that everyone is working towards the same objectives.

Step 5: Foster (and Model) a Culture of Collaboration and Accountability

A legendary sales team works together towards a common goal. 

It starts by encouraging teamwork, open communication, and constructive feedback. But as the leader, modeling it is more important than any plan you put in place. 

You need to live and breathe that culture, or your team will (perhaps unconsciously) see that it is unnecessary for success. It will start to slip, and you won’t be able to rebuild it without starting from scratch. 

Advanced Sales Strategies

Once you've started building your sales team and see your business growing, it’s time to take it to the next level with some advanced sales strategies. 

Implementing these strategies takes effort and investment, but the rewards are worth it. 

Account-Based Selling

First up, we have account-based selling. This is a targeted approach where you build relationships with high-value accounts. 

Tom Scearce of TOPO (now Gartner) published a comprehensive Account-Based Everything (ABE) framework, which requires the entire company – sales, marketing, customer service, etc. – to work together on big clients. 

He argues that companies often try to employ account-based marketing strategies that are too narrowly focused and don’t include the other operational arms. 

By broadening that approach, you can ensure better customer success results, leading to higher retention rates and larger purchases. 

Social Selling

Social selling is one of the biggest targets right now. Success in the 21st century requires social media to build relationships with potential customers and generate leads.

Use LinkedIn, Twitter, and Instagram to engage with prospects and share valuable content that showcases your expertise and builds trust. This will help you reach a wider audience and build a stronger online presence.


Co-selling is another game-changer that can take your sales team to the next level. 

It's all about collaborating with another company that speaks to your target audience and offers a complementary product or service. By teaming up, you can combine forces and provide a more comprehensive solution to your customers.

But here's the thing: finding the right co-selling partner is crucial. You need to look for a company that shares your values and has a similar customer base but offers something different that can add value to what you're already offering. 

Always Keep a Foot in the Game

There is a common mistake that I see many entrepreneurs fall into the trap of making, which I want to help you avoid.

Even though you are building a sales team to handle the bulk of your sales demand, it doesn't mean you should step away completely. 

To lead, you must stay involved in the sales process, continue building relationships with clients, and keep a pulse on industry trends and market demand. It doesn’t mean 50 cold calls daily, but involving yourself in a particularly high-value negotiation or answering regular inquiries can keep your skills sharp.

It's also important to continually invest in your own personal and professional development. Take courses, attend workshops, or work with a coach or mentor. Investing in yourself can improve your skills and knowledge, help you stay motivated and engaged, and keep your business moving forward. 


I wish I had known all this when I first started. I avoided delegating for too long, then built the wrong kind of team when I was finally ready to give up some control. 

If you want to take your business to the next level, you need to build that legendary sales team behind you. A great team can generate new leads, close bigger deals, and drive massive growth, freeing up your time to focus on other areas of your business.

If you want to hear more about this, check out my full conversation with Kris, as he dropped a lot more knowledge. 

That’s it for this week; thanks for reading.

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