🥇 #1 Freelance Tool on G2 — 2026
Most Efficient — ProductHunt 2026
🏆 Best Automation Award — Freelancer Awards 2026
💚 47,000+ freelancers trust Otto
💰 Average $14,200 recovered per freelancer per year
4.9/5 stars across 6,200+ reviews
🚀 Connect your inbox in 30 seconds
🔒 SOC 2 Type II Certified — Bank-grade security
Otto is live in 47,000+ inboxes right now

Your freelance business,
on autopilot.

Our mission

Give every freelancer a full-time back office — without the overhead. Connect your email in 30 seconds and Otto handles invoices, contracts, scope creep, and client follow-ups so you never lose a dollar to admin again.

Otto reads your inbox, learns your clients, and runs your back office automatically — so you can focus entirely on the work that pays.

First month free·Cancel anytime·Works with your existing email

Works with
📧Gmail
🔷Outlook
🏢Office 365
🟡Yahoo Mail
🔵AOL Mail
🍎Apple Mail
📮Any IMAP inbox
$0
Average recovered per freelancer each year
0s
To connect your inbox and go live
0%
Of Otto-drafted follow-ups approved by users
0
Freelancers using Otto worldwide
What Otto does

Everything your admin day costs you — automated

Freelancers lose 6+ hours every week to non-billable work. Otto handles all of it — invoices, scope, contracts, taxes, proposals, and client relationships.

📧

Invoice follow-ups

Otto drafts perfectly-timed, human-sounding follow-ups for overdue invoices. Review and approve, or set automated sends after your trust threshold.

🚨

Scope creep detection

Otto reads new client messages and flags when requests exceed your original scope — then drafts a professional change order for your approval. Stop losing $15k/year to free work.

📋

Contract generation

Describe a project in plain language or a voice note. Otto generates a clean, professional contract with payment terms, revision limits, and kill fees — ready to sign in minutes.

📄

Proposal drafting

Leave a voice note after a client call. Otto transcribes, prices, and formats a full proposal ready to send — in minutes, not hours.

📈

Cash flow forecasting

Based on your invoicing patterns and client history, Otto predicts exactly when money will land — and alerts you to gaps before they become a crisis.

🔁

Client re-engagement

Otto tracks when clients go quiet and drafts warm, natural check-in messages so no relationship slips through the cracks.

📊

Income dashboard

Real-time view of what's invoiced, what's outstanding, and what Otto has recovered — all pulled automatically from your inbox.

💰

Rate benchmarking

Otto compares your effective hourly rate to market data in your city and specialty — and tells you exactly what you're leaving on the table.

🗓️

Tax reminders

Quarterly estimated tax deadlines, how much you owe, and a direct payment link — calculated from your actual year-to-date income.

How it works

Up and running in under 5 minutes

No new accounts, no integrations, no manual entry. Connect your email and Otto figures out the rest.

1
~30 seconds

Connect your inbox

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.

2
automatic

Otto learns your business

Otto reads your last 90 days of email to detect your clients, invoicing tools, rates, and communication style — no manual setup required.

3
ongoing

Review, approve, or automate

Otto surfaces drafted messages for your review. Approve, edit, or skip — or set trusted automation for repeat tasks once you're comfortable.

Your AI assistant

Just ask Otto 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.

📝
"Draft a scope change email for Acme Corp — they want 2 more revisions beyond what we agreed"
📋
"Generate a contract for the Jordan Lee project — $4,500, 4 weeks, 2 revision rounds"
💵
"What's my cash flow looking like for the next 30 days? Should I be worried?"
📊
"Which clients haven't paid on time historically? Flag them before I take on new work"
Otto Assistant
Active
AR
Acme Corp just replied asking for two more logo concepts. We only agreed to one. Can you handle it?
Got it. This is out-of-scope — your agreement with Acme was 1 logo concept + 2 revisions. I've drafted a change order: $600 for the additional concept. Want to review it before I send?
✓ Send change order ✎ Edit first 📋 View draft
AR
Perfect. Also — what's my cash position looking like this month?
You have $8,400 confirmed income. $6,200 outstanding — Acme ($2,400) is 14 days late, Meridian ($3,800) is 7 days late. At your average collection rate, expect ~$4,800 to land by end of month. I'd recommend following up on Meridian today — I've drafted a message.
Ask Otto anything about your business...
The dashboard

Everything in one place

A clean command center for your freelance finances — income, outstanding invoices, and what Otto has been doing on your behalf.

Income this month
$8,400
↑ 18% vs last month
Outstanding
$6,200
2 invoices overdue
Effective hourly rate
$94
Market avg: $138
Otto recovered (30d)
$3,800
↑ 3 invoices closed
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
From freelancers

What happens when admin runs itself

"Otto recovered $4,200 in overdue invoices in my first month. The follow-ups sound exactly like me — clients have no idea it's automated."
SK
Sarah KimBrand Designer · NYC
"I used to spend Sunday nights doing admin. Now I spend 3 minutes reviewing what Otto drafted and I'm done. The rate insight made me raise my prices 40%."
MR
Marcus RiveraFreelance Developer · Austin
"The proposal-from-voice-note feature is magic. I recorded a 2-minute note after a call and had a $6k proposal ready to send in 8 minutes."
JL
Jamie LoweUX Consultant · London
Pricing

Simple pricing. No surprises.

Start free. Upgrade when Otto pays for itself — which usually takes about a week.

Starter
$0
First month free, always
  • Works with any email provider
  • Invoice tracking & overdue alerts
  • 3 Otto-drafted emails per month
  • Basic income dashboard
  • Tax deadline reminders
Agency
$79
per month · up to 5 seats
  • Everything in Pro
  • 5 connected inboxes
  • Team invoice overview
  • Shared approval queue
  • Custom style per seat
  • Priority support

Stop doing admin.
Start doing work.

Connect your inbox in 30 seconds. Otto starts working immediately.

Create your account

Start your 30-day free trial

Enter your email and we'll send you a one-time access code. No password, no credit card.

Already have an account? Sign in instead

🔒 Bank-level security 👁 Read-only inbox access ✕ Cancel anytime
📬
Check your inbox

We sent a 6-digit code. Enter it below to continue.

Resend code  ·  Change email

You're in!

Setting up your workspace…

📧
Connect your email
30 seconds · just one click
🔍
See what Otto found
automatic · nothing to do
👋
Tell us about you
2 minutes · optional fields
✍️
Your writing style
1 minute · just tap chips
🚀
You're done!
Otto starts working immediately
🔒Bank-level encryption
👁️Read-only — Otto can't delete anything
Revoke access anytime, instantly
Cancel subscription anytime
Step 1 of 5 — Connect your email

Let's connect your email 📧

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!

🔒 Totally safe. Otto can only read your emails — it can never delete, move, or send anything without your personal approval first.
🔒 Read-only access  ·  Bank-level encryption  ·  Revoke anytime in 1 click
🎉 Your inbox is connected! Otto just scanned your last 90 days of email.

Look what Otto found! 🔍

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.

💡 Tools with a green checkmark are already being tracked. The ones without will be watched for in future emails.
🟧
FreshBooks12 invoices found ✓
🔵
PayPal8 payments detected ✓
🟣
StripeConnected via email ✓
📋
NotionProject threads found ✓
📐
FigmaWill watch for it
📅
CalendlyWill watch for it

Tell us about you 👋

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.

The more you share, the more Otto sounds like you. Your name will appear on contracts and proposals automatically.

How do you like to write? ✍️

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.

🎯 No right or wrong answers here! Just pick what feels natural. Otto will learn your style more over time.
Warm & personal
Professional
Short & sweet
Formal
Casual
Friendly
Direct & clear
Detailed
Every 3 days
Every 7 days (recommended)
Every 14 days
I'll do it manually
🎉

You're all set!

Otto has already read your last 90 days of email and found a few things that need your attention. Here's your quick snapshot:

3 things Otto is ready to help with

2 unpaid invoices · 1 client who's gone quiet · Your Q2 tax estimate

$6,200
Unpaid invoices found
5
Active clients tracked
$94/hr
Your current rate
👉 Your dashboard is ready. Click the button below and Otto will show you exactly what to do first — no guessing required.
Your 30-day free trial starts now. No credit card needed.
Workspace
Account
Agent status
Otto is active
Your free trial ends in 7 days — upgrade to keep Otto running your business.

Good morning, Alex ☀️

Otto drafted 3 items overnight — ready for your review

FRI · MAY 2, 2026
AR
Income this month
$8,400
↑ 18% vs last month
Outstanding
$6,200
2 invoices overdue
Effective hourly rate
$94
Market avg: $138
Otto recovered (30d)
$3,800
↑ 3 invoices closed
Invoices
ClientAmountStatusDueAction
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
Pending approvals
3 items
Invoice follow-up · Acme Corp · $2,400 · 14d overdue
"Hi Sarah, I wanted to follow up on invoice #1042 for $2,400 due April 18th. I know things get busy — could you confirm when payment is expected? Happy to help with any questions."
Proposal ready · Marcus Wright · Voice note 9:14am
"Hi Marcus, great chatting today. Attached is my proposal for the brand identity project — 6-week timeline, $4,500 total, 2 rounds of revisions. Let me know if you'd like to adjust anything."
Client re-engagement · Marcus Wright · 47 days silent
"Hey Marcus, hope you're well! It's been a little while — wanted to check in and see if you have any upcoming projects I could help with. Always happy to catch up."
Agent activity
● live
Payment received — Studio Nine
$1,800 · Follow-up cancelled
2m
📄
Proposal drafted from voice note
Marcus Wright · $4,500 · Awaiting approval
14m
📧
Follow-up drafted for Acme Corp
Invoice #1042 · 14 days overdue
41m
👁
Proposal viewed — Jordan Lee
48hr follow-up window started
2h
⚠️
Contract clause flagged
Unlimited revisions · Revisions Group NDA
Yesterday
💰
Invoice #1038 follow-up sent
Meridian Studio · $3,800 · Day-7 nudge
Yesterday
⚠ Scope alert
Action needed
Acme Corp — Logo Project
"Can you also mock up two alternative directions? We want to see more options."
Original scope: 1 concept + 2 revisions. This request adds ~4 hours of unbilled work (~$380 at your rate).
Q2 Tax deadline
JUN 15
44
days remaining
Estimated owed$3,240
YTD income$28,400
Effective rate~22%
Already paid Q1$2,890
Rate insight
UI/UX · Austin
Your rate
$95/hr
Market median
$138/hr
Your rate is 31% below market for senior UI/UX designers in Austin. You're leaving roughly $18k/year on the table at your current volume.
📋
Contract
Customize the fields on the left, then send or download
Contract details
Otto
Your AI assistant · active
Hi! I drafted 3 items overnight — 2 invoice follow-ups and a scope alert for Acme Corp. What would you like to handle first?
Just now