Guidesly Unleashes Jack AI, the First Vertical AI for Outdoor Recreation

The software arms race in vertical SaaS just paddled into new territory. Guidesly, the platform powering thousands of outdoor adventure guides, has launched Jack AI™, a first-of-its-kind AI assistant built specifically for the outdoor recreation industry. Its mission? Free up guides from the modern digital grind and let them focus on what they do best: delivering unforgettable outdoor experiences.

Fresh off a $10 million Series A raise in January, Guidesly is turning that capital into product firepower—starting with Jack AI.

The New MVP of the Outdoors: Jack AI™

Whether they’re leading fly-fishing trips or backcountry hikes, today's guides aren’t just wilderness experts—they’re also expected to double as content creators, SEO specialists, and social media managers. Jack AI aims to automate those extra hats.

Guides upload a few photos and notes after a trip, and Jack AI does the rest—generating a trip summary for clients, fresh SEO-friendly website content, and social-ready posts. All automatically. All editable. And all done in minutes.

“The beauty of Jack AI is that in a couple of minutes, the computer is doing what used to take me an hour,” says Rich Adler of Tuna Wahoo Charters in West Palm Beach. “Time is money—and this saves both.”

Built for Guides, by Guides

Jack AI wasn’t dreamed up in a boardroom. It’s the product of five years of real-world feedback from thousands of working guides and the personal experience of David Lord, Guidesly's founder and a lifelong angler himself.

“We built Jack AI to solve the pain points no one else was touching,” Lord explains. “It’s not just AI—it’s Vertical AI designed specifically for the realities of guiding.”

Unlike generic marketing tools, Jack AI is tightly integrated with Guidesly’s proprietary platform. That means the system gets smarter with each trip booked, enhancing personalization, local search visibility, and client re-engagement. Think of it as your marketing intern who also knows how to fish.

Results That Matter

While many companies talk about “AI-powered growth,” Guidesly has the data to back it up:

• 3x increase in bookings for top guides using Jack AI

• Significant boosts in website traffic and social reach

• Hours saved per week, translating into real-world revenue

• $0 cost—Jack AI is free for all registered Guidesly Guides

Why This Matters

The launch of Jack AI signals a broader trend in AI: the rise of verticalized solutions that don’t just offer automation, but deep, domain-specific value. In this case, Guidesly is tapping into a market that’s traditionally been underserved by tech: the $1 trillion outdoor recreation industry, where small operators are the norm.

And in an industry where trust, authenticity, and customer experience are everything, Jack AI’s ability to amplify a guide’s voice without replacing it is key. This isn’t ChatGPT for fishing trips—it’s AI with boots on the ground and reels in the water.

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