The average freelancer loses 20–50% of their working week to non-billable admin — proposals, follow-ups, contracts, scope battles. Otto eliminates all of it. Connect your email in 30 seconds and your AI back office is live.
64 million US freelancers juggle the same chaos: feast-or-famine cash flow, late payments, and clients who push scope. Otto ends all three — automatically, in your voice.
First month free·Cancel anytime·Works with your existing email
Proposals, e-signatures, payments, scope protection, follow-ups, cash flow, tax prep — everything Bonsai and HoneyBook do, plus an AI that actually runs it for you.
Leave a 2-minute voice note after any call. Otto transcribes, scopes, and formats a professional, branded proposal — ready to send while competitors are still typing.
Attorney-vetted contract templates for every freelance scenario — web design, photography, consulting, retainers. Send, collect legally-binding e-signatures, and close in minutes, not days.
Accept credit card, ACH bank transfer, or payment plans directly from your invoice. Automated reminders go out before and after due dates. No more chasing checks.
Every client gets a branded portal where they can view proposals, sign contracts, make payments, and check project status — without logging into anything. Zero friction for clients.
Otto reads new client messages and instantly flags requests that exceed your signed scope — then drafts a professional change order. Stop giving away $15k/year in free work.
Human-sounding follow-up sequences that go out on your behalf — at exactly the right time, in your voice. Clients have no idea it's automated. Average recovery: $4,200 in month one.
Feast-or-famine cycles are the #1 reason freelancers quit. Otto predicts when money will land based on your invoicing history, flags dangerous gaps weeks in advance, and prompts you to line up work before the famine hits.
Otto compares your effective hourly rate against real market data for your city and specialty — and gives you a script to raise your rates at exactly the right moment.
Quarterly estimated tax deadlines, how much you owe, expense categorization, and 1099 contractor tracking — all auto-calculated from your actual income. Your accountant will thank you.
Start a timer from any project, or log hours manually. Otto auto-populates your invoice with billable hours and flags if you're undercharging based on your contracted rate. No separate app needed.
Forward any receipt or connect a bank card. Otto reads the merchant, amount, and date — then categorizes it as a business expense automatically. Tax season becomes a one-click export.
Upload any contract a client sends you. Otto flags risky clauses — unlimited revisions, IP ownership landmines, non-competes, kill-fee gaps — before you sign anything you'll regret.
No new accounts, no integrations, no manual entry. Connect your email and Otto figures out the rest.
Works with Gmail, Outlook, Office 365, Yahoo, AOL, Apple Mail, and any IMAP inbox. Read-only access — Otto never touches emails you don't approve.
Otto reads your last 90 days of email to detect your clients, invoicing tools, rates, and communication style — no manual setup required.
Otto surfaces drafted messages for your review. Approve, edit, or skip — or set trusted automation for repeat tasks once you're comfortable.
From first inquiry to final payment — Otto covers the entire lifecycle. No tool-switching, no copy-paste, no manual anything.
Otto isn't just a dashboard — it's a full AI assistant that can take on tasks in natural language. No menus, no forms. Just tell it what you need.
A clean command center for your freelance finances — income, outstanding invoices, and what Otto has been doing on your behalf.
"Otto recovered $4,200 in overdue invoices in week one. The e-signature contracts closed three times faster than my old DocuSign flow. Clients literally say my process feels 'enterprise-level' now."
"I went from 6 tools — Notion, Wave, DocuSign, Calendly, PayPal, Google Docs — to just Otto. The scope creep detection alone saved a $9k project from going sideways. And the rate benchmark told me I was 40% under market. I've raised my prices twice."
"Voice note to $6k proposal in 8 minutes. Client signed the e-contract that same evening. Payment was in my account 2 days later. That entire pipeline used to take me a week and four tools. Otto is the first freelance tool that actually gets how I work."
Start free. Upgrade when Otto pays for itself — which usually takes about a week.
Otto adapts to your industry — your contracts, your rate benchmarks, your client communication style.
Other platforms make you do the work. Otto does it for you.
| Feature | ✦ Otto | Bonsai | HoneyBook | Manual |
|---|---|---|---|---|
| Proposals & contracts | AI-generated | ✓ | ✓ | – |
| E-signature | ✓ | ✓ | ✓ | – |
| Online payment processing | ✓ | ✓ | ✓ | – |
| Reads your inbox automatically | AI-native | – | – | – |
| Scope creep detection | AI-native | – | – | – |
| Automated invoice follow-ups | Sounds like you | Basic reminders | Basic reminders | – |
| Voice note → proposal | AI-native | – | – | – |
| Rate benchmarking | Live market data | – | – | – |
| Cash flow forecasting | AI predictions | – | – | – |
| Time tracking | Built in | ✓ | – | – |
| AI expense categorization | Auto-categorized | Manual entry | – | – |
| AI contract review | Flags risky clauses | – | – | – |
| Setup time | 30 seconds | ~2 hours | ~3 hours | Forever |
The ones freelancers ask before they realize Otto is the obvious choice.
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Setting up your workspace…
This is the only step that takes any effort — and it's just one click. Pick your email below and Otto does the rest. That's it!
Otto automatically spotted these tools in your inbox. You don't have to do anything — it'll track all invoices and payments from these automatically.
Almost done! This helps Otto write emails in your voice and put your name on contracts. Everything here is optional — fill in what you're comfortable with.
Otto writes emails, proposals, and follow-ups that sound exactly like you — not like a robot. Just tap the words that match your vibe. You can change these anytime.
Otto has already read your last 90 days of email and found a few things that need your attention. Here's your quick snapshot:
| Client | Amount | Status | Due | Action |
|---|---|---|---|---|
Acme Corp #1042 | $2,400 | 14d overdue | Apr 18 | |
Meridian Studio #1038 | $3,800 | 7d overdue | Apr 25 | |
Jordan Lee #1044 | $1,200 | Due in 3 days | May 5 | |
Studio Nine #1040 | $1,800 | Paid | Apr 30 | |
Marcus Wright #1043 draft | $4,500 | Draft | — |