Building an Early Stage Leadership Team

When building an early-stage leadership team, there are two major components to consider — experience and culture. It’s critical for founders to surround themselves with people who have complementary skill sets and diverse backgrounds, and equally critical to ensure those people fit the mindset and mission of the company.?

These need to be intertwined, and approached strategically with an accurate evaluation of where you are and what you need at any given time. In the early stages, for example, culture is a much more important part of building a leadership team. It’s higher impact and more foundational within a small company just getting its start.?

As a founder, building a leadership team is one of the hardest things you’ll encounter simply because the stakes are so high. One bad hire within a small group of people can take a long time to iterate and fix, while big, established companies can compensate for those missteps by installing other people around them.?

As a founder, building a leadership team is one of the hardest things you’ll encounter simply because the stakes are so high.

The best way to avoid bad hires is to simplify — what do you absolutely need within your leadership team to build the company you’ve envisioned? What do you need to take the idea you have and turn it into something of substantial value within the first two years? What are the key gaps you are trying to fill or work that you believe needs to get done that you are not able to execute on.?

Start by identifying and clearly defining your market. Are you creating a new category, or taking on an established incumbent in an existing one? What product or solution are you actually setting out to create??

From there, evaluate yourself within the context of what you’re trying to achieve. What are you, as a founder, not best suited to take on? You can’t do this alone. Self-awareness and an honest assessment of your own skills or weak spots will help you surround yourself with the right people.?

You can’t do this alone.

For example, as an IT professional I ran into a lot of startups that were built around a very real frustration the founders had encountered as end-users. That’s fantastic at the outset, but it’s important to hire people who have never encountered that problem, too. This will help promote long-term viability by expanding the possibilities and applications of your work beyond that original pain point. Once you’ve solved that problem, you’ll need to keep adding value. And that’s where a wide swath of experience within the leadership team really comes into play — the identification of new opportunities you may never have even considered.?

Many early-stage companies acquire customers with founder-led sales. A typical motion is introductions from a venture investor to a C level Exec in their network. I’ve met several founders who can do a sales pitch well. I’ve also met founders who can’t. I know plenty of my CIO friends who are open to meeting early-stage companies but walk away not being convinced that they need the solution. When I ask why they respond by stating that they enjoyed hearing about the product but could not get excited from what they heard or agree that it was enough of a priority. It’s clear in most of those cases that the founder needs a sales leader around them who could have delivered a more convincing pitch.?

Founders, think about what skills and abilities you need at your existing stage. This will depend on a multitude of factors, like product maturity, the space you’re in, and the culture of the industry you’re trying to address. If you are a cybersecurity company, for example, it’s very difficult — if not impossible — to sell a new product if you don’t come from that background or have someone within your core team who does.?

Figure out what you need in the next 6-12 months.

If your product isn’t ready today, think about what skills and capabilities you’ll need to add to your team in order to get there. Is your biggest need early customer acquisition? Do you need a VP of sales to start building your pipeline or someone with a customer deployment background who can talk about implementation? Do you need someone to engage and enable potential customers? An experienced marketer to build out your messaging and positioning or just focusing on demand generation?? Figure out what you need in the next 6-12 months. Ensure you’re properly filling in the blanks and addressing customer needs by understanding what you need.?

You don’t have to fill all the gaps in the team right away. Think about the type of leader you need for company building not just product building. For example who will take on some fundamental areas like finance or customer success until you can hire someone to lead it.?

An effective leadership team is made up of executives who not only have a track record, but who understand you and what you’re trying to achieve. If you’re coming into an existing space, there are probably things you don’t like about it and what to change or fix. Be up front about these by essentially stating why the time is now for your product. It’s okay to be contrarian, as long as you communicate your stance clearly. Elon Musk, for example, has decided that nobody is going to buy his cars in a showroom. Apple has decided that their products will come with a specific retail experience, too. Both companies are maniacally focused on customer experience, which is in direct opposition to the way most of their competitors behave. They both seem to be doing alright. As one of the favorite artists Bob Seger sings, "Don’t be afraid to blow against the wind." It’s completely fair to start by saying, “Here’s what I don’t want to replicate about this industry.” Just make sure you’re aligned with your leadership team.?

From a cultural perspective, it’s important to define the guard rails early. Ask yourself what kind of company culture you want to build, and then communicate that honestly and directly to your leadership. When bringing together people of different backgrounds with different styles and experiences, alignment is key. Good houses are built on a good foundation, and that’s how you should approach executive hiring. You can remodel and change the interiors when needed, but if the house doesn’t have a good foundation, it won’t stand for long.?

When bringing together people of different backgrounds with different styles and experiences, alignment is key.

A big part of instilling good leadership culture comes from how you manage the leadership team as a founder or CEO. In early stage companies, everyone has more than one job. That doesn’t mean big company hires won’t fit, but you’ll need to make it clear that there are no defined roles within a startup and that leading one is not a 9-5 job. Learn about your potential leadership hires. Find out what they want to achieve. How hungry are they? Do they match your hunger level, and share your values? Do they have an appreciation for the product? My personal belief is that to be an effective leader at any stage, you’ve got to love the product.?

You’ll also need to think about how you make decisions together. Startups need to be able to think and act quickly, it’s their primary advantage over big companies. Focus on accountability and empowerment. Give your leaders both the tools and the trust to make a decision, and foster an environment in which they’re comfortable being accountable for that decision. You want agility and speed, you want to keep things moving forward, acquire new customers, get into production, produce marketing collateral, and so much more. All of these things will never get done if you’ve built your leadership culture around a single decision maker.?

Similarly, how do your leaders deal with mistakes? As a startup, you’re going to collectively make a ton. Are your leaders accountable, flexible, strategic and creative? The ability to positively and productively deal with failure is a prerequisite for success.?

For early stage startups, building the right leadership team can be the difference between long-term viability and a quick fizzle out. The hires you make here will impact every aspect of your company. Investors will look at whether or not you have the go-to-market chops within your group. Potential customers will look for people who speak their language. Prospective employees will want to work for leaders who celebrate success, and learn from failure. Diversity of experience within your core leadership team allows you to ensure these far flung bases are covered, always.?

Leadership hiring is hard. You will make mistakes, and that’s okay. It’s how you deal with them and learn from them that will ultimately dictate your long-term success. Think less about the executives you want in place, and think more about the partners you want around the table. In the early stages, partnership and camaraderie amongst the leadership team is as important as anything else. These are the people you’ll go to battle with, who you’ll win with, and who you’ll lose with. Think about who you’ll most want on your team when the chips are down.

Think less about the executives you want in place, and think more about the partners you want around the table.