From AI Products to an AI Company: Windward’s Internal Gen AI Journey

By Ami Daniel, Co-Founder & CEO, Windward

At Windward, we’ve always believed in staying ahead of the curve. But with Gen AI, the curve isn’t just shifting—it’s exploding.

This isn’t just another tech wave. It’s a fundamental rewiring of how we operate, build, and scale. So we made a clear decision:

AI isn’t a feature. It’s a foundation.

We’re not dipping our toes in. We’re transforming the company—end-to-end—with AI at the core.

Rethinking Every Workflow

We’ve started reimagining every major process in the company. Not just optimizing. Rethinking.

• Content creation is now AI-augmented. Our marketing team drafts faster, tests more ideas, and personalizes messaging at scale. 
• Legal and compliance reviews are supported by prompt-based contract analysis.
• Sales team members augment their preparation by using AI tools tailored to our customers, products, and specific needs.
• Customer Success team members automate playbooks & workflows, risk alerts and KYC elements.
• R&D: a natural place for implementing AI. Most of our team is already leveraging tools like Windsurf and other frameworks. 
• Product: Our UX designers use tools like V0 and Figma, PoCs are powered by agents built on Amazon Bedrock, and market research blends multiple AI tools with proprietary data. The result? A dramatically shortened path to discovering product–market fit.
• Support & data Operations: Many support workflows and data augmentation processes now leverage our suite of AWS-powered vertical agents.
• Internal reporting and analysis — from forecasting to performance tracking — are being rebuilt through automation and intelligent agents.
• People: from recruiting to promotions and role changes, from onboarding to training, AI is at the core of every decision. We are rolling out multiple AI bots powered by our proprietary data and vertical knowledge.

This isn’t about reducing headcount. It’s about moving our people up the value chain—from gathering and processing data to making decisions and delivering impact.

AI Fluency: Now a Core Skill

Every new hire is expected to come in curious, open, and capable with AI tools. Whether you’re in engineering, product, sales, or ops, AI fluency is the new baseline.

We measure it. We teach it. We expect it. In every interview, I personally ask each candidate: “How did you prepare for this interview, and how did you use AI to support your success?”

And if you’re already at Windward, you’re part of this transformation.

Internally, we’re giving every employee access to top-tier Gen AI tools and setting time aside to learn and experiment. Whether it’s chaining prompts or building internal copilots, we want everyone building. 

Zapier recently published their framework for assessing employees’ AI skills. We plan to adopt a variation of this framework later this year.

Our Stack Is Changing

We’re doing a full audit of our internal tech stack—and rebuilding with an AI-first lens. This means:

• Replacing legacy tools with AI-native alternatives
  
• Automating repeatable workflows
  
• Building internal bots to manage knowledge, compliance, onboarding, and more
  

We’re embedding Gen AI into both the backend (automating document processing, customer risk narratives, and compliance workflows) and the frontend (prompt-based risk alerts, decision support, and user-facing recommendations).

Many departments are being transformed to be 10x more technical. Roles that were “manual” (e.g., writers and analysts), are now being redefined to be way more technical and require engineering background, infusing engineers into every department in the company. 

This isn’t a patch. It’s a rewrite.

It Starts With Our Data

None of this works without the right foundation. The real magic of AI isn’t just models—it’s data.

We’re doubling down on clean, proprietary, well-managed data.

We’ve spent years structuring the maritime world. That’s our advantage. Now we’re feeding our models this data, ensuring our Gen AI outputs are precise, explainable, and trustworthy.

The Rules of Scaling a Company Have Shifted

AI can’t just feel productive — it has to be productive.

So we’re building a framework to track productivity improvements across workflows.

Where we used to ask “How long will this take?”, we now ask:

• How much of this can AI handle?
  
• How fast can we get to a better decision?
  
• How do we free up our people to focus on higher-order thinking?
  
• How can we scale with limited hiring?
  

This isn’t theoretical. We’re already seeing AI reduce effort by 10% – 35% in multiple flows.

The Bigger Picture

This isn’t about AI replacing people. It’s about amplifying people.

It’s about giving our teams leverage.

It’s about moving from information gathering to intelligent action.

At Windward, we’ve always believed in fusing human expertise with machine scale. Now, we’re taking that to the next level with AI-native products, AI-enabled teams, and a mindset that embraces change.

This is our shift from AI-friendly to AI-first.

It touches everything: hiring, onboarding, product, process, culture.

It starts with the people we bring in. And it continues with the way we build.

If you’re reading this as a teammate; your job is changing.

If you’re reading this as a customer or partner; our value to you is changing too.

We’re moving faster. We’re thinking bigger.

And we’re building a future where AI isn’t just in the product…

It’s how we work.