Underboss — Business finances automated with AI and backed by human oversight.

Your AI Finance Manager — Desktop & Mobile

Run your business.
We'll run
your finances.

Underboss connects every session with pricing, payment, and client into one system — so your billing, collections, and bookkeeping happen on their own, without the manual work in between.

Business finances automated with AI and backed by human oversight.
Start for free →
+
Underboss,
at your service
Ask questions, record events,
or request account insights. Try:
· "Astrid had a session today"
· "What's Nikki's balance?"
· "Show me session totals by
  tutor for last month"
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Why You Need Underboss

Research shows manual billing leaks revenue every single month.

5–10%
Revenue lost to billing friction
Missed invoices, unclear pricing, and slow follow-up quietly erode money you’ve already earned.
1.5
Days per month on billing admin
Chasing payments, reconciling sessions, and fixing bookkeeping errors eat time you could spend on clients.
#1
Pain point: late or missed payments
For service businesses, the gap between work done and money received is where everything falls apart.

*SurveyMonkey Small Business Research 2025

Who it's for

Built for service businesses

Tutoring
Businesses
Executive &
Business Coaches
Fitness
Instructors
Music
Teachers
Therapists
Performing Arts
Studios
Educational
Centers
Wellness
Providers
And more...

If your business runs on recurring client relationships, Underboss was built for you.

How it works

Your finance function—handled.

Underboss manages the financial side of your business from end to end and lets you have multiple users.

Pricing

Handles custom rates, packages, and unique pricing with ease.

Invoicing

Automatic invoices that are accurate and on time.

Payments & Collections

Cash, check, Venmo, or card — every payment tracked automatically in one place.

Customer Communication

Smart payment reminders, follow-ups, and client updates sent automatically — keep clients informed without lifting a finger.

Bookkeeping

Transactions are organized and reconciled automatically.

Business Intelligence

See what’s happening in your business anytime, anywhere.

The Underboss difference
AI does the work.
Humans make sure
it's right.

Most financial software just processes data and hopes for the best. Underboss is different — our team actively monitors your account, checks that the numbers make sense for your business. You get the speed of software with the judgment of a person who actually understands service businesses.

The AI handles
The routine work
Session tracking & pricing
Invoice generation & sending
Payment reminders & matching
Bookkeeping & reconciliation
+
backed by
Our team ensures
It's actually right
Data makes sense for your business
Anomalies are caught and corrected
Workflows stay tuned as you grow
You’re never flying blind
Desktop & Mobile

One system. Every screen.

Underboss works on desktop and as a mobile app — so whether you're at your desk or between sessions, your clients, billing, payments, and bookkeeping are always with you.

App Store
web.underboss.app
Underboss
Dashboard
Money
Reports
Clients
Services
Team
AI chat
Settings
Dashboard
Welcome back, Kimberly
Next steps
All set! You're ready to go.
Recent transactions
DateNameActivityProviderAmount
Jun 12 ThuSarah MitchellSession · Math tutoringKimberly$95
Jun 10 TueAlex ChenSession · Reading supportKimberly$80
Jun 9 MonMaria TorresSession · Science tutoringKimberly$95
Jun 7 SatJames ParkSession · Writing tutoringKimberly$80
From our users

Real businesses. Real results.

It handles everything from session tracking to payments, and the automatic reminders are a huge help. The app simplified our entire process.

Susan Gotschall, M.Ed, C-SLDS
Susan Gotschall, M.Ed, C-SLDS
Dyslexia therapist & founder, Reading and the Squid Tutoring

The automatic matching of payments is a life-saver. I save hours each week and can finally focus on coaching instead of chasing payments.

Axel Lönnfors
Axel Lönnfors
Youth soccer coach and former player
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Get Started

Stop running your finances.
Start running your business.

Sign up today and make Underboss a part of your team.