You had an amazing idea for a new product, and you made the leap into starting a company. It worked. You’re one of roughly a third to half of seed-stage founders who make it all the way to Series A. That’s an impressive feat.

Now things get harder. What got you here won’t get you to the next stage. More than a third of Series A companies never make it to Series B. The research on why is pretty consistent: it’s not about the product, it’s whether you can shift from operator to orchestrator.

At Seed and early Series A, the founder is the one getting things done. Designing the product, closing sales, managing vendors. That hustle and expertise is what was required. The next stage asks for something different: building and leading a team that gets things done while the founder focuses on strategic initiatives.

This is where things break down. Hiring the wrong people. Hiring the right people but never actually empowering them to move things forward. Failing to build a culture where everyone shares one vision and feels comfortable disagreeing on how to get there. Those are the factors that often prevent companies from making the next step.

Startup Boston

I was at Startup Boston last week, and RI Startup week is going on now. As you’d expect, it’s packed with content for founders and the venture capitalists who back them. Surprisingly few sessions cover what it actually takes to lead a startup, most are tactical: marketing, finance, how to pitch investors, and of course, AI.

The numbers highlight why that’s concerning. Only about 15 to 35 percent of seed-funded companies reach Series B, and by Series C that number drops to roughly 6 percent. Even clearing the operator-to-orchestrator shift once doesn’t mean you’re safe. It simply gets you to the next level, where the stakes are even higher.

A company surviving this gauntlet is one thing. The founder surviving it is another. Of the small number of companies that do make it to Series C, fewer than half still have their original founder in the CEO seat.

Leadership vs Communication: Yes…And

When most people think of leadership, they think of the person who has all the answers, can solve every problem, and knows what to do next. That’s not wrong, it’s just incomplete.

It’s no accident that the things I write and speak about are both leadership and communication. As a leader, it’s not enough to be a great communicator, it requires communicating in brand new ways. Leading a team of three people who are all experts in your technical field is quite different from explaining how the product works to the new marketing hire, or explaining to the board why a specific tool is worth the investment.

It’s no longer enough to explain how something works or how to get something done. The new job is different: telling the story of why the product matters in a way that makes people feel it, sharing your vision and your passion, and inspiring others to take action.

Hiring for culture can be a trap

Of the factors I mentioned that cause problems, hiring is often the place where things start to break down. A very common mistake leaders make is hiring people who “fit the culture.” Creating a good culture is critical to success, but hiring for it can be a serious problem. When hiring for culture, it’s easy to choose the person who feels the most comfortable, rather than the person with the actual skills and knowledge needed.

Founders can take specific steps when interviewing to avoid this trap and prioritize people who first and foremost fulfill the needs of the organization. Once you clear that hurdle, you can filter for the energy and attitude needed to not only fit in, but help build the culture you want.

Help is out there, but is it a fit for you?

Plenty of leadership training courses exist. Franklin Covey, Dale Carnegie, and American Management Association all have fantastic offerings. They’ve trained millions of people and have a well-documented track record. The problem is that they’ve trained millions of people. That means they have to work for everyone, which means they don’t address the specific challenges a startup founder faces.

On the flip side, there are large venture capital firms that hire organizations which specialize in coaching startups. These firms require large retainers up front, but if many of the companies in their portfolio need coaching, the return on investment makes it worth the money.

If individual coaching is too expensive and generic leadership courses don’t quite do the trick, there’s room for something in between. A program built specifically for founders, small enough to stay personal, but structured enough to work through the actual challenges of scaling a team rather than leadership in the abstract. A dozen founders in a cohort accomplishes a few things at once: the cost drops enough to be genuinely affordable, the focus narrows to problems founders actually face, and the relationships built with a group of peers become a resource of their own.

Want to learn more?

Whether you’re a founder feeling this hiring trap right now, or you’re on the investor side watching a portfolio company hire for comfort instead of capability, the results can affect your financials, and even the survival of the business.

Because it’s so important, I’m hosting a webinar on this exact topic. Why it’s crucial to hire people who challenge you, how to hire the right people, and how to bring them on board so they’re fully engaged in helping you fulfill your vision. Sign up here to join this thirty minute, interactive session. As a bonus, at the end of the session I’ll share details on a founders cohort I’m building based on exactly the model described above. If it feels right for you, there’ll be a discount code for the next cohort.

If you are attending an Startup week activities, let me know! I’d love to hear your thoughts and perhaps meet you at a session.