Selling in Complex Markets

Selling in complex markets often forces startups to think beyond conventional wisdom. While most advice focuses on product-market fit, pricing strategies, and customer engagement, real-world examples show how growth sometimes comes from unexpected, even controversial, tactics. These approaches may raise eyebrows, but they also spark important questions about what it takes to break through.

Take Skydio, for example. Instead of navigating the slow, bureaucratic process of public-sector procurement, they introduced their drone technology to law enforcement agencies through philanthropic donations. This move allowed them to get their product into the hands of users quickly and build momentum that could lead to future contracts. For a startup without the resources to chase RFPs for months on end, it was a clever way to show value upfront.

Still, it raises a question. If a startup sidesteps procurement through donations, is that unfair to others competing through standard processes? Or is it simply resourceful, a smart way to cut through red tape and level the playing field against bigger companies? For any startup eyeing the public sector, Skydio’s story is a reminder that understanding the system is just as important as working within it. And sometimes, finding a way around it can change the game.

Another example is Gili Ra’anan’s Cyberstarts model in cybersecurity. Instead of waiting to earn credibility, startups in the Cyberstarts portfolio benefit from advisory input directly tied to fund performance. CISOs who advise also help shape and test early products, and in return, their input becomes part of the startup’s go-to-market advantage. The results speak for themselves. Startups come out of the gate with real traction and real logos.

But there is controversy here too. Some argue this kind of arrangement blurs the line between genuine feedback and pay-to-play. If a CISO has skin in the game, can they truly remain objective? On the flip side, others see it as a sharp alignment of incentives. Everyone involved wants the product to work, because everyone benefits when it does. Whether you agree with the ethics or not, the model shows how critical it is to get buy-in from the right people early on.

Then there is Y Combinator. The startup ecosystem it has built is unmatched in terms of peer support, fast feedback loops, and early traction. Startups sell to each other, test quickly, and build momentum in a trusted environment. For a founder trying to get to product-market fit, that kind of concentrated energy can be transformative.

But it can also be misleading. Just because your product works within the YC bubble does not mean it will succeed in the wider world. Outside of that circle, customers are not friends, and adoption takes longer. The real market has more friction, more skepticism, and a different pace. Founders who win inside YC still need to prepare for the uphill climb that comes after demo day.

What all of these stories have in common is not just creative sales tactics. It is an understanding that selling is not purely about solving a problem. It is about strategy, relationships, credibility, and timing. A great product helps, but it is not always enough on its own.

Startups that succeed often build on strong networks. They know how to position themselves where it matters. They are not afraid to take an unconventional path, but they also think carefully about the long-term consequences. Whether it is Skydio working around procurement, Cyberstarts leveraging aligned incentives, or YC creating its own early-market sandbox, these examples show how selling in complex markets requires more than persistence. It requires intention.

For founders, that means thinking bigger than just features or pricing. It means asking who influences decisions, how credibility is earned, and what systems stand in the way. When those answers are clear, the path forward might still be hard, but at least it becomes visible.