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. Read More »

The easiest ROI booster that most entrepreneurs miss

From day one of starting a business, so much entrepreneurial mind share goes to figuring out ROI. Every dollar counts. You start hiring people. Their salary is cash out of your pocket. When they screw up, it costs you.

The business grows. Complexity increases. The search for ROI improvements continues. For most businesses, people investments add up. They can be the largest single expense line.

So what do entrepreneurs do to maximize the output of the team? Most of the focus falls to hiring, firing and intense management of performance. Hire top performers. Expect great things. If they turn out to be a dud, fire them. It sounds harsh, but this is a reality. When an investment isn’t paying off, move on.

The problem with this cycle is cost. Many expenses associated with employee turnover are invisible. The end-to-end process burns a pile of cash. So entrepreneurs focus on better hiring, better on boarding, faster firing. It’s an expensive way to learn.

There is a cheaper, faster, and simpler habit you can develop. It won’t cost you a dime. And if you’re not using it already, it’s guaranteed to boost your ROI.

The ah-ha moment

Chatting in office croppedA colleague of mine relayed a story to me. He was meeting with the CTO and founder of a billion dollar start-up success story. Over coffee the CTO shared a recent revelation. He had come to appreciate the ROI of asking his team about their weekend. People worked harder and gave more to the company because he showed interest in the personal lives of his team.

I shared this story with a senior leader at another company. Her response: “Wow, that’s exactly what we need. If we could get our CEO to do that… to say good morning to the team… to show he cares… it would revolutionize our company.”

Why it matters

In the early part of my career I worked in a team of 12 people reporting to an executive. He was my second-level manager so I didn’t interact with him much. But I did have full appreciation that my career rested in his hands. He came in every morning and went right to his desk. He never said hello and rarely acknowledged me. Some days it made me anxious, other days it pissed me off. In both cases it affected my creativity and contributions to the company. Read More »

The secret to boosting innovation… and the catch.

Flower lightbulbWhat if there was a secret that guaranteed your company an exponential innovation boost? And what if there was a small group of people who had figured out this secret? And what if that group was willing to share every intimate detail of that secret for free? Would you be interested?

I’m guessing you would jump at the chance.

Now, what if there’s a catch to learning this secret? And what if that catch requires you to challenge every personal belief you hold about leading business? Would you still do it?

Last week I spent three days with the people who hold this secret. They came together from all over the world to meet in two connected conferences. One in Hungary and one in Canada. These are deep thinkers. Explorers. They share an intense passion for figuring out a better way to run businesses. And together, they’ve found a secret they are willing to share.

Sometimes secrets are so big and so scary, we don’t want to hear them. This could be one of those secrets.

The need for change

Like it or not, our world is changing. With change comes disruption. With disruption comes discomfort. In business, this discomfort is showing up through disengagement. Right now 76% of full-time employees are open to new job opportunities. This raises a big question. How innovative is someone in their current job while thinking about working somewhere else?

The Google generation is looking for a new way of contributing. Power structures no longer work when everyone has access to the same information. Hierarchies collapse when everyone has an equal voice in the virtual world. Sub par ideas get crushed when power structures can’t protect them.

Yet we still aim to be innovative in organization structures designed for a different time. Read More »

Why you should avoid hiring an HR leader for your company

I have a sinking feeling when I hear that a young company is hiring their first HR leader. I’ve seen this story play out many times. Too often it goes awry, ending months later with everyone frustrated. The people involved are well intentioned. And I get it. The team is growing. People issues are cropping up. The internal running of the company is becoming a distraction. Hiring a multi-talented HR person seems like the right next move.

Why HRI often get calls from headhunters looking for names of potential candidates. The call usually goes something like this: “I have a client, early stage, led by an entrepreneur. The company is looking for a Director of HR. Someone who is strategic and can also get their hands dirty in the day-to-day stuff. Do you know anyone?”

These people are extremely difficult to find. Developing business strategy is a completely different skill set from handling the multitude of day-to-day issues.

The company thinks they need this role, but maybe they don’t. When I get one of these calls, I try to orchestrate a conversation with the CEO so I can share my experience.

What does HR do?

Having run HR teams in my past life, I know there is no limit to the things that keep HR busy. The question becomes, how much of that work is adding measurable value? And for the work that needs to be done, who is best to do it? Read More »

Entrepreneurs: 5 watch-outs before you engage an advisor or hire an executive (or choose a co-founder)

I’ve seen the same dynamic play out in every start-up led by a 20 or 30-something founder. Sometimes it’s fatal. More often it wastes valuable time and burns through precious resources.

Picture this. The proverbial plane takes off with the founder at the controls. The founder wants to get as high as possible, quickly. There is turbulence. A wicked storm is on the horizon. The passengers start to whisper, “we need more experienced people flying this plane.” Privately, the founder is questioning his (or her) abilities to fly a jumbo jet. He hasn’t even mastered flying a Cessna. He sees another plane further ahead on the flight
path and wants to gain the experience of that pilot. He grabs the radio and makes a request that he will soon regret.

There is a combo of naivety and enthusiasm that turn great ideas into growing companies. That enthusiasm is often accompanied by a need for speed. A need to learn fast and implement faster. Read More »

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