The switching question
Switching software is scarier than staying on a bad spreadsheet. Let's talk about that.
Most operators who talk to us are already convinced their current setup is costing them — that's why they're here. What keeps them from moving isn't doubt about the product. It's the quiet list of what could go wrong: a migration that drags, owners noticing the mess, being locked in, betting on a small vendor. Those are reasonable fears, so this page answers them the way we answer everything — specifically, in plain English, including the parts that aren't flattering.
Question one
What does onboarding actually involve?
Three steps, and we do the heavy ones with you. First, we connect your PMS and start pulling bookings — that's hours, not weeks, and nothing about your current operation changes while it runs. Second, we stand up your branded owner portal and load your properties, owners, and fee rules. Third — the real work — we reconcile your first month together, so the first statement an owner sees from Sherpa is one you've already checked line by line against your books.
The honest part: how fast this goes depends almost entirely on the state of your books. Current QuickBooks and clean fee rules move quickly; books that need cleanup first are real work. We'll give you a straight timeline on the demo call once we've seen what you're working with — before you've paid us anything, not after.
The other honest part, straight from our drawbacks page: our deepest PMS integration is the one we run ourselves. Newer PMS connections get the core data flowing but may lag on edge cases. Ask us specifically about yours — you'll get a specific answer.
Question two
Will it connect to what I already use?
This is the version of the switching question that actually decides things, and it's the one you shouldn't have to book a call to answer. You can log in, open Configuration → Connections, and hook up your own stack. Here's everything that plugs in today, named, so you can check your list against ours before you talk to anybody.
Property management
- Uplisting
- Hostaway
- OwnerRez
- Guesty
- Hostfully
- Hospitable
- Track
- Lodgify
Paste an API key or access token and we verify it against the provider before saving.
- iGMS
- Escapia
- Streamline
If yours isn't on either list, that's the first thing to tell us.
Accounting
- QuickBooks Online
QuickBooks Online connects by signing in to Intuit — there's no key to paste. Connect as many companies as you have; each one's tokens are stored separately.
- Sage Intacct
- Xero
Today QuickBooks Online is required for the owner-statement products, and it's the one dependency we can't work around.
Payments
- Stripe
Stripe uses a restricted key you create, with the steps laid out in the app. Read on charges, balance transactions, customers, disputes and payouts — and nothing else.
- PayPal
- Braintree
- Authorize.net
Sherpa never asks for write access on anything in Stripe.
Channels & market data
- Airbnb
- PriceLabs
- Wheelhouse
- Google Business Profile
Airbnb connects through a browser extension that uses your own signed-in session, re-checked daily. PriceLabs and Wheelhouse connect with their own API keys.
Airbnb has no public API for this data, so the extension is the honest way to get it. It's covered on our drawbacks page.
Whatever you paste is encrypted before it's stored and never shown back to you — to rotate a key you replace it rather than read it. Sherp, our Slack assistant, is in beta and connects the same way when you want it.
None of this means you have to do it alone. Onboarding is still done with you, on a call, if that's what you'd rather. The point is that finding out whether Sherpa fits your stack doesn't require one.
Question three
Can I switch mid-season, or do I have to wait for the slow months?
You can switch mid-season, because nothing switches off. Sherpa runs alongside whatever you use today — your PMS keeps taking bookings, your current reporting keeps working, and you cut over to Sherpa statements only when a month has reconciled and you trust what you see. There is no day where the old system is off and the new one isn't proven yet. That cliff is the thing people actually fear, and the parallel-run approach simply removes it.
That said: if you're choosing, the best month to start is the one before you wish you'd started. Every operator we've met — ourselves included — waited one owner-statement crisis too long.
Question four
What happens to my data if I leave?
It leaves with you. Bookings, statements, expenses, and reports export to CSV, Excel, and PDF while you're a customer — the same exports your bookkeeper uses day to day — and if you cancel, you take all of it, exactly as our pricing page has always said. We don't charge for exports, we don't slow-walk them, and we don't hold your history hostage to keep you. A vendor that needs to lock the door to keep customers has already told you what it thinks of its product.
Question five
You're a small company. What if Sherpa stumbles?
Fair question — we ask it of every vendor we use, too. Three things are true. First, Sherpa isn't a startup burning runway toward a pivot: it's the software an operating company built for itself and runs its entire portfolio on, every day. It exists because Nomad needs it to exist. Second, the promises above are structural, not contractual courtesy: 60 days' notice on any change, and your data exports completely — so the worst case is an orderly exit, not a cliff. Third, we publish our real numbers on the open dashboard precisely so you never have to wonder how the business behind the software is doing.
We won't pretend the risk is zero — we said the same on our who-this-is-not-for page. If you want a ten-year-old vendor with a support department, that's a legitimate preference and we'd rather you know now.
In writing
The safety rails, in plain terms.
60 days' notice on any change
Any change to your price comes with 60 days' notice and the option to walk away. Already published on our pricing page — repeated here because it's the promise that matters most.
Your data leaves with you
Bookings, statements, expenses, and reports — exportable while you're a customer and handed over in full if you leave. No hostage-taking, no export fee. It's the same promise printed on our pricing page.
Onboarding is done with you, not to you
White-glove means we connect your PMS, stand up your owner portal, and reconcile the first month together. You are not handed documentation and wished luck.
We run our business on it too
Every door Nomad Hospitality manages runs on the same production system you'd be using. If it breaks, our own owner statements break. That is the real SLA.
Still have a "yeah, but…"?
Good — bring it to the demo. Thirty minutes with Josh, in the live product, and the switching question that's specific to your operation gets a specific answer. If the honest answer is "don't switch yet," you'll hear that too.