Scout InsurTech Spotlight with Douglas Craver

Douglas Craver is the Founder & Managing Director of Orchestration, an implementation partner that equips business ventures, both early-stage and later-stage, with the knowledge and leadership necessary for optimizing and automating operations, as well as a Tech Leadership Coach & Career Advisor at The Operative, guiding today’s innovators to become the leaders they aspire to be. Douglas was interviewed by Michael Fiedel, Co-Founder at Scout InsurTech and Co-Founder at PolicyFly, Inc.

Doug, why do you think so many founders focus on raising venture capital before finding clients, and what risks does that create?

“When you look at it objectively, a lot of founders mistake raising venture capital for having a business strategy. It feels like validation. If a VC is interested, they think, ‘I must be onto something.’ But that’s not the same as having paying customers.

Part of this is human nature. It’s tough to grind away alone, maybe with a cofounder or a couple of peers, and not get much recognition. Social media makes it harder. You scroll LinkedIn, and it feels like everyone is announcing a new round of funding. That creates pressure to keep up, even if those founders don’t actually know where their peers stand with customers. Talking to investors can feel easier than the hard work of building, iterating, and finding clients.

The risk is that you give away control too early. Venture capitalists are looking for the best deal, and if you walk into those conversations without revenue, you’re negotiating from weakness. If you walk in with paying customers, even if you’re profitable by just one dollar, you’re operating from strength. You also run the risk of shaping your product to please investors instead of customers. Once you start raising, you rarely stop. You’re perpetually fundraising, and that keeps you from the feedback loop that comes only from real clients. Too many founders burn through capital and build large teams before they’ve proven product-market fit. That’s when the business can spiral.”

What lessons can early-stage founders take from your experience using pre-license agreements to both validate a product and fund growth?

“Pre-license agreements put discipline into the process because they force you to seek real validation. An investor telling you they like your idea doesn’t mean there’s demand. A customer agreeing to pay before the product launches is validation.

The process forces you to get out from behind your computer. You have to talk to potential customers, network on LinkedIn, dig into forums like Reddit, and find out where people are voicing the pain point you’re trying to solve. That’s when you know you’re onto something.

In my own experience, we got discovered through app stores. Executives would search there to see what new tools were emerging. That visibility led to a pre-license deal with a large specialty insurer, which not only validated what we were building but eventually led to them acquiring us.

That experience taught me a couple of things. First, early revenue is more powerful than any pitch deck. Second, pre-license deals give you credibility with investors before negotiating equity if you decide to raise. And finally, they let you maintain control over your vision. You’re not building based on what investors think you should build. You’re building based on feedback from the people who are actually going to pay for the product.”

What practical steps should a founder take to identify and win their first beta customer?

“Networking is the foundation. Either you or someone on your team needs to be out there in the industry. In the Insurtech space, events by Scout InsurTech are great because they showcase what’s happening and put you in front of potential buyers.

But networking can’t stop there. You need a consistent cadence of communication. That might be a short monthly update on what you’re building. Keep it simple, but let people see your progress. It doesn’t have to be about building a big personal brand on LinkedIn, though that can help. It’s really about staying top of mind to generate interest through your story.

Digital outreach is equally important. Use LinkedIn to expand your network, and don’t overlook forums like Reddit. People in those communities talk openly about the challenges they face. Even if they aren’t the decision-makers, they can point you to referrals. Over time, build a list of contacts who have shown interest. Send them updates, keep them engaged, and don’t be afraid to ask for introductions.

This is blocking and tackling. It’s not glamorous. It’s daily or weekly work, testing different messages, seeing what gets a response, and learning from the feedback. Eventually, that consistency and persistence will lead you to your first beta customer.”

When do accelerators truly add value, and when might founders be better off finding clients on their own?

“I tell founders to think about accelerators the same way they think about investors. Look at their pedigree. Do they specialize in your industry? Can they show wins with companies like yours? Have they helped founders land their first customers or navigate compliance? If the answer is yes, they can add significant value.

Accelerators can expand your network, provide exposure to potential customers, and help you navigate regulatory environments that might otherwise hinder your progress. In industries like insurance or healthcare, that can be critical.

But accelerators are not always the right move. If you already have strong connections, understand compliance, and know how to reach customers, an accelerator may slow you down. It’s a trade-off of time. If it doesn’t increase your velocity, it’s not worth it.

I also caution founders against using accelerators as a substitute for discipline. If you’re joining one because you don’t like doing certain things, that’s a red flag. As a founder, you have to learn to do the hard, unglamorous work. Success often comes from getting good at the things you don’t enjoy. An accelerator isn’t a replacement for that. It should amplify your efforts, not compensate for what you lack.”

How should founders balance building a scalable product with addressing the immediate needs of early customers?

“This is one of the toughest challenges. Early customers will want customization. They’ll push you to build features that fit their specific needs. If you say yes too often, you’ll end up with tech debt and a product that doesn’t scale. But if you ignore them, you risk losing the trust of the very people who are helping you validate the product.

The key is to start with a transparent roadmap. Share it with customers and use it as the framework for deeper conversations. That way, they understand where the product is headed, and you can evaluate their requests against your long-term vision.

It comes down to learning to say no more often than yes. That’s not easy. It’s human nature to want to please customers. But discipline matters. Strong product discovery and development methodologies help, as do consistent engineering practices. They give you a process for making decisions that balance short-term needs with long-term goals.

I’ve always been a fan of Marty Cagan and the Silicon Valley Product Group. His book Inspired was basically our bible when we were building Mobile Defense. We followed those principles to the letter, and sure enough, we were acquired. When I told Marty that story, he just nodded and said, ‘Let me guess, you got acquired.’ He knew because their product methodologies work.

The bigger picture is that fundraising can distract from this work. Once you start raising, it becomes a permanent job. I tell founders to think carefully before going down that path. If you’re working nights and weekends to keep your venture alive, don’t assume raising money is the only way out. Do what you have to do, whether that’s delivering food, contract work, or whatever it takes, to stay independent long enough to build the product you believe in. Independence gives you the freedom to say no, to stick to your vision, and to grow sustainably.”

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