Five tips to building (or rebuilding) your first sales team

Ready to move beyond entrepreneur-as-solo-salesperson?

Tried already and disappointed with the results?

This article’s for you.

One of the biggest challenges for most entrepreneurs is building their first sales team. Sales provide the essential fuel that makes tomorrow possible. Company founders carry a lot of that responsibility in the earliest days. And if all goes well, the need to build a sales team comes fast. Without the team, opportunities will dwindle.

As founders we tend to have one of two views of sales. We’re either born to sell and love to be in every deal. Or we can’t wait for someone else to take over. Both offer challenges when it comes to building the team.

To get a fresh perspective on how to best tackle this phase of growth, I reached out to Andy Aicklen. Andy has been driving hyper-growth in software and tech companies for over thirty years. He now works with venture capital firms to maximize returns from their software investments. Andy and I shared stories and compiled the following list of tips for founders as they build their teams.

Deciding what you need

Do you hire a heavy hitter or an energetic new grad? Manager first or pure hunter? There are many needs to balance.

Although there is no single right answer, there are a few important elements to consider. Some of the questions that Andy asks founders include, “What are you selling? How long is the sales cycle? What’s the expected average monthly and annual run rates? How technical is the product? Who is the buyer?”

There’s a big difference in hiring someone to manage a short, simple sales cycle versus  a long, complex one. “Big deal” sales people can inspire a customer to stay engaged for the long haul. They help customers get to a place they didn’t think they could get to. They understand customers at a deeper level. They know how to leverage people on the team. They have an advanced level of social skills. They are also expensive.

Often product knowledge gets too much focus. From Andy’s perspective, “Understanding the technology and product isn’t that big an issue. Do you want your people to be experts in the product or an expert in selling? If they are too product-focused they won’t be successful long-term in managing a large number of clients. I’d rather hire a salesperson who was a sale executive first and a subject matter expert second. That’s why we use sales engineers or product specialists”.

Spend time upfront. Figure out exactly what you need before building a sales team with the wrong mix of skills for what you’re trying to sell.

Investing in the right people

Most founders have limited experience in hiring staff. Nowhere does this skill gap matter more than when hiring sales talent. Perhaps we’ll write a more in-depth blog later on running an effective sales hiring process. For now, I’ll highlight three of the biggest mistakes we see in hiring the first few members of the team.

Cash is usually tight in the early stages so entrepreneurs look for low cost options. In Andy’s words, “They try to go cheap. They hire lower than average sales people, often paying a small salary with a higher commission rate.” This model rarely pays off. Low base, high commission packages only work for high volume, easy sales (like commodities). Unless your product or service is flying off the shelf, good sales people won’t be willing to bare all the risk. The type of individual who signs up for  this form of compensation plan is naive or desperate.

There is a candidate pool available of seasoned sales people with impressive resumes. It’s a tempting group to consider. These are the folks who’ve had a great run at a successful company. They are appealing because they appear to have had success and offer the sales acumen you need. But many times they are old school. They were trained to sell in a different generation to a different generation. Unless they’ve sold to your demographic, beware.

Andy shared a great story that highlights a third mistake. John was a young up-and-comer who thought of himself as a sales superstar. He had great sales numbers and was earning a boatload of cash. He rewarded himself with a Porsche and a new house. If he had applied to your company, you might well have hired him. It turned out that John had caught a wave. He was selling a super hot product with a strong sales proposition. In Andy’s words, “anyone who showed up for work could make money selling that product, people just needed to buy.” Within a year the market opportunity had dried up and John was into the tough slog of sales. He couldn’t do it. His career in sales was over. The moral of the story: Great sales numbers don’t guarantee a proven seller.

Save yourself six months of wasted time and money. Invest in hiring the right person upfront. Look for professional sales people who have achieved results in more than one job at more than one company.

Recognizing that your sales team is not you

You are an expert in your product and industry. You’ve got a network. Most important, you have the ultimate decision-making power. You can craft a new product on the fly. Pricing is your call. Business terms are yours to write and to change.

Even your best sellers don’t have the complete package when they start. Your job is to get them there. That takes work. Don’t expect your sales team to hit the ground running. They aren’t even at the starting line yet. They should be considered as consciously incompetent when it comes to selling your solution.

Managing a sales team can be tedious and repetitious

Entrepreneurs hate the necessary monotony of managing a sales team. As a result, the required focus and rigorous structure gets missed. From Andy’s experience, “As companies start to grow, I see them having the best intentions to put structure in place. And then they get distracted. They get caught up in writing articles, making keynote speeches and dealing with customer issues. They get pulled away from the focused discipline of managing sales. Momentum slows down.”

When you think about your priorities for the upcoming week, what’s top of the list? Maybe it’s going to New York to hire two people. Maybe the focus is on a critical customer deadline. It’s not sexy, but managing the sales process needs to be at the top of the list.

Your job as founder and entrepreneur? Maintain a weekly regimen with forecast calls. Drill down and understand what’s going on. Even if you have a sales manager who is responsible, don’t rely on them 100%. Inspect. Get involved in the top 5 deals (or more). Stay involved in the ones you’ve already closed. The first customers are taking a lot of risk by working with you and need your attention.

Knowing your strengths

Andy leads sales training for new entrepreneurs. He starts by asking who in the room feels they are a confident salesperson. A few tentative hands go up. Most founders don’t have sales DNA. The initial sales get closed through an intense drive, contagious energy, and product knowledge.

If you are not a born salesperson and haven’t had years of experience, how do you coach and mentor your sales team? It’s a problem. You might be able to tell your sales people what to do. But that’s a short term bandaid leading to long term pain.

Consider hiring a good sales coach. For a small investment, you can have a seasoned expert at your side. They can coach you. Or they can coach the team alongside you.
Intrigued by what you’ve read? Check out the Building Blocks coaching program. I coach leaders on building a strong foundation unique to their growing business. You can reach Andy through his email aa@andyaicklen or through his website at

Leave a Reply

Your email address will not be published. Required fields are marked *

Show Buttons
Hide Buttons