/ frequently asked
Questions, answered.
Will it send emails I haven't seen?
Not for the first 14 days. During your trial, every reply is drafted and dropped in your Gmail Drafts folder for you to review and send. After 14 days, you can flip on auto-send per-agent if you want. Many of our clients keep auto-send off forever — drafts in Drafts Folder is the killer feature, not auto-send.
What if it makes a mistake?
AI drafts are drafts. Treat every one as a draft. The platform tracks accuracy by counting how many drafts you approve unedited vs. edit vs. reject — those numbers show up in your weekly digest. If a particular intent (quote requests, schedule changes) shows low accuracy, we tune the model context and try again. We never charge you for a draft you didn't send.
Does it work with Outlook / Yahoo / my custom domain?
Yes. Anywhere you can generate an email "app password" (Gmail, Outlook, Yahoo, most cPanel hosts), Cherokee AI works. We auto-detect IMAP/SMTP servers for the major providers. For a custom domain we'll walk through the settings on the onboarding call.
How is it different from a virtual assistant?
A VA costs $1,000–$3,000/mo and works business hours. Cherokee AI ships a custom setup (priced after your free audit), works 24/7, and inherits your voice from the first email you give it. A VA learns your voice over weeks. A VA quits. Cherokee AI doesn't. Different tool — both legitimate. For most one-truck businesses Cherokee AI is the better answer; for a 10-person business with complex client relationships, probably both.
Can I cancel?
Anytime. From your billing portal, one click. No "talk to retention," no "minimum commitment." You stay active through the end of the current billing period (so you don't lose what you already paid for) and you don't get charged again.
What happens to my data if I cancel?
It's deleted within 90 days. Your customer email content is never sold, never shared, never used to train AI models. See Privacy Policy and Data Processing Addendum.
Do I need to give you my Gmail password?
No — never your real password. You generate a single-purpose "app password" in your Google account that's specific to Cherokee AI. You can revoke it anytime in your Google security settings. We can read your inbox and send replies from your address; we cannot access any other Google service. We walk through this on the onboarding call.
What about reviews on Yelp / BBB / Angie's / etc.?
Today: Google Reviews only — that's the one that affects local-3-pack ranking the most. Adding Yelp + Angie's is on the roadmap. If you need broader coverage, mention it and we'll prioritize it.
I'm not technical at all — is setup hard?
Onboarding is a 30-minute screenshare call. You don't write code, you don't configure anything past pasting a Gmail app password. We build your setup with agent swarms while we walk through it — by the end of the call you're live and a draft is in your Drafts folder.
Why are you doing this?
I (Jesse) run a painting business in Cherokee County, deep in the Appalachian Mountains. I built this for my own inbox first. Cherokee AI Solutions is the productized version. I'd rather build software that helps contractors than answer "what's your availability?" 12 times a day. Your subscription pays for the platform infra and lets me keep building it.
Where are my AI replies generated?
Anthropic's Claude (Haiku model). Anthropic's enterprise terms apply: your customer email content is not used to train models. We do not share your data with any other AI provider, ad platform, or third-party.
What if I want a feature you don't have?
Tell me. Email hello@cherokeeai.com with what you'd want. If it fits inside an existing setup, the agent swarm can usually ship it same-day. If it's a new agent shape, give us 24–48h. The platform was built for one painting business and grew from there — that's how features get added.
