Underboss for Coaches
Coach clients.
Not
spreadsheets.
Business and executive coaches build their reputation on trust and results — not invoices and payment reminders. Underboss handles the billing side of your coaching business automatically, so your client relationships stay focused on the work.
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Underboss,
at your service
at your service
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or request account insights. Try:
or request account insights. Try:
· "Rachel completed her session"
· "What's Marcus's balance?"
· "Show me retainer revenue this quarter"
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Clients
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·
The coaching business problem
Your clients pay for your expertise. Not your invoicing system.
01
Retainer billing is easy to let slip
Monthly retainers and multi-session packages are the backbone of a coaching business — but manually invoicing them on time, every time, is one more thing competing for your attention.
02
Chasing a client undermines the relationship
You’re in a position of trust and authority with your clients. Sending a third “just following up on this invoice” message erodes that dynamic in a way no other service business quite experiences.
03
Renewals get lost in the gap
When a coaching engagement wraps up, there’s often a natural moment to renew — but if the billing is clunky or the conversation awkward, clients drift away instead of rolling over into the next phase.
What Underboss does for you
Three things coaches need.
One system that handles them.
01
Retainers and packages on autopilot
Set up your monthly retainers, multi-session packages, or intensive pricing once — Underboss invoices them automatically on schedule. Whether you charge a flat monthly fee or bill per engagement, every client gets the right invoice at the right time without you thinking about it.
02
The system does the chasing, not you
Payment reminders go out automatically before a balance is overdue — so the nudge never has to come from you personally. Clients can pay by card or bank transfer, and every payment is matched instantly. Your relationship stays clean; the awkward part disappears entirely.
03
A clear picture of your business, always
See active clients, outstanding balances, and monthly revenue at a glance. Know exactly where each engagement stands — so when a retainer is coming up for renewal, you’re having the conversation from a position of clarity, not scrambling to figure out what was agreed.
“The automatic matching of payments is a life-saver. I save hours each week and can finally focus on my clients instead of chasing invoices. It just runs in the background and everything stays straight.”
DH
Executive & leadership coach, 18 active retainer clients
Desktop & Mobile
One system. Every screen.
Underboss works on desktop and as a mobile app — so whether you're between sessions or at your desk, your clients, billing, payments, and bookkeeping are always with you.
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Next steps
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Recent transactions
| Date | Name | Activity | Amount |
|---|---|---|---|
| Jun 12 Thu | Rachel Odom | Session · Executive coaching | $1,200 |
| Jun 10 Tue | Marcus Webb | Retainer · Leadership Q2 | $2,500 |
| Jun 9 Mon | Diane Forsythe | Session · Strategy intensive | $900 |
| Jun 7 Sat | James Park | Session · Business coaching | $750 |
Get Started
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Start running your coaching business.
Sign up today and make Underboss a part of your team.
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