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About Sherpa Data

I built Sherpa Data because I needed it.

Hi — I'm Josh Kristoff. I started Sherpa Data as an internal toolset for Nomad Hospitality, my 80+ property short-term rental portfolio in Jacksonville. Other operators kept asking if they could use it, so I opened it up. What you're looking at is the result.

Josh Kristoff

Founder

Josh Kristoff

Founder, Sherpa Data · Managing Partner, Nomad Hospitality

How I got here

Navy → Meraki → Nomad → this.

Six years in the Navy

I started as a Surface Warfare Officer out of the Naval Academy. Six years at sea, 20+ countries, leading teams of 200+. Ended as Chief of Staff to a two-star admiral — living in Bahrain, running programs that had to work the first time because the next watch was counting on them.

Cisco Meraki — building tools for the teams building the product

I joined Cisco Meraki in 2017 as a Technical Program Manager and stayed four years, eventually running Strategic Data Projects. The job was "the Next Generation Operating Model for Meraki" — building the internal tools used by the product, design, engineering, and operations teams day to day. I also ran the Executive MBA at Wharton (Business Analytics + Marketing/Ops, Director's List) during those same years. The biggest lesson: leverage comes from giving the people already doing the work better tools to do it with.

Nomad Hospitality — two families, 80+ doors

In 2021 my wife Kass and I teamed up with another couple — Jered and Carly — to start Nomad Hospitality in Jacksonville Beach. Today it's 80+ active short-term rental doors (30 more in renovation) plus 70 long-term doors, part of Nomad Capital Ventures: a vertically integrated group with hospitality, realty, design/construction, and asset-management arms. We built the business we wanted to operate.

Sherpa Data

Running 80 doors surfaced the same spreadsheet problem I'd been solving for engineering teams at Meraki — the tools exist, but not for us. Enterprise PMS pricing, owner reports that took Sunday nights, market data sold like an enterprise contract. So in April 2024 I started building what Nomad needed, one module at a time. Other operators saw it and asked if they could use it. Sherpa Data is what came out of that.

We use it daily

Nomad runs on Sherpa.

Every Sherpa Data product ships in our own operation before it ships to customers. Our revenue manager uses RateAlpha daily. Our owner reports come out of Folio. Our direct booking site is a Sherpa Sites build.

When a bug hits us first, it gets fixed first. When a roadmap call is hard, I ask which version would I actually use on Monday.

Nomad Hospitality direct booking site

How I build

Principles, not slogans.

Operator-first

Every Sherpa product runs in Nomad Hospitality before it ships to customers. When a bug hits, it hits us. When a feature matters, it's because we needed it.

Transparent

Every number has a source, every recommendation has reasoning, every alert has a why. No black-box "trust the AI." You should be able to trace any answer back to the data that produced it.

AI-native, not AI-first

AI is a tool that makes operators faster — not a replacement for judgment. We use it where it earns its keep (search, synthesis, categorization) and stay out of the way everywhere else.

Built for operators like us

Enterprise hospitality software is priced and shaped for 500-unit chains. Sherpa fits operators running 1–500 units — the people we live alongside in this business.

The team using it

The Nomad team on Sherpa.

Jered D.

Managing Partner — Nomad Hospitality

I used to spend hours each month piecing together reports in QuickBooks just to give owners a basic snapshot. Sherpa took that off my plate completely. Now it just runs — and I stay out of the weeds.

Carly D.

Managing Partner — Nomad Hospitality

Managing multiple QuickBooks accounts across properties used to be a mess. Sherpa brought structure and automation to our reporting — no more juggling exports and formulas. It feels like we finally have the right tool for the job.

Talk to me directly.

30-minute demo, operator to operator. I'll open the product, map it to your portfolio, and show you what would fit. No sales rep in between.