Shouldered AI / AI bookkeeping and getting paid
Invoices out. Late payers followed up. Books matched.
AI bookkeeping is AI that handles the routine finance work of a business. Shouldered AI's Finance Desk, run by a Hero named Matthew, sends invoices, follows up with late payers, matches the books and flags bills. Your accountant still makes the decisions.
"I do invoices on Sunday nights."
Invoices go out when the job is done, so Sundays are yours again.
"Chasing late payers is awkward."
Polite, steady reminders go out on a schedule you set, so you get paid without the awkward calls.
"My books are a mess at tax time."
Transactions are matched as you go, so your accountant gets clean books.
"Will AI make money decisions for me?"
No. It prepares and tracks. Financial and tax decisions stay with you and your accountant.
Seven desks. One HQ.
Tells you each morning who paid and who is late.
Sends invoices as soon as work is marked done.
Follows up with late payers on a polite schedule.
Matches payments and transactions to the books.
Flags bills coming due and anything that looks off.
Prepares simple reports for you and your accountant.
Simon runs HQ: all the tech and all the brain power, and the one you talk to. Each of the seven desks is run by a Hero, and Simon directs all seven and answers for them. A person approves what matters, and legal, tax, medical and financial decisions stay with you and your licensed advisers.
Three jobs finish today, and three invoices go out within the hour. Two customers who are ten days late get a friendly reminder, and one pays by afternoon. Yesterday's payments are matched to the books, and a supplier bill due Friday is flagged for you.
An illustration, not a promised result.
Start
Start with the Small HQ: up to 5 seats and 80 hours a month, $750 a month paid for the year (Founding price: $500, first 50 companies only), plus $1,000 onboarding once. Every seat comes with a Hero.
Grow
As invoices pile up, add hours at $12.50 or move to Medium.
Your Hero is here to improve the human. Your HQ, led by Simon, is here to improve your business.
Two prices, and 50 Founding places.
First, what the work costs you today. A full-time office manager runs most small businesses about $4,000 to $5,000 a month with taxes and benefits, and goes home at five. Every call nobody answers is a job that goes to someone else.
Business coaching often costs $5,000 to $7,500 for one session day. HQ does the work every month, with a coach running the Shouldered Way and workshops included. Already have a coach? HQ works alongside them.
Founding 50: of 50 places left. When they are gone, this price closes.
For you
An assistant for one person: mail, chat, calendar, to-dos and contacts. It learns how you work.
- A seat a month
- $25
- Founding price, first 50 only
- $20
- A seat a month. Cancel any time
- No onboarding fee
- It stops where you stop. It does not run a business
Up to five people
5 seats and 80 hours a month. Onboarding $1,000, paid once.
- Paid for the year
- $750
- Month to month
- $1,100
- Founding price, first 50 only
- $500
- Simon and all seven desks
- Starts the work itself
- About $25 a day, paid for the year
- The six-month guarantee
- Arrives in December. Join the founding list now
Six to twenty people
20 seats and 200 hours a month. Onboarding $2,000, paid once.
- Paid for the year
- $1,875
- Month to month
- $2,750
- Founding price, first 50 only
- $1,250
- Everything in Small
- Room to grow without changing plan
- The six-month guarantee
Prices are per month. Only the first 50 companies (the Founding 50) get the Founding price with a two-year commitment, paid yearly by bank transfer, and keep it for as long as they renew. Pay yearly by bank transfer and take 3% off. Onboarding is $1,000 for Small and $2,000 for Medium, paid once, and free at Shouldered events. It is one 1-hour call: technical setup with our technical team first, then your business with our team. The person who sold you HQ joins your onboarding call. Paid for the year, you get a named person who checks in every month. Month to month gets standard support. Twenty-one people and up is built around you. More seats are $25 each (Founding price $20), and more hours $12.50 each; hours count only while HQ is working, like minutes on a phone plan.
Enterprise and government. For large companies and public agencies. Custom plans start at $5,000 a month. Pilots are paid. We start SOC 2 Type 1 work in 2027. Texas agencies: we are working toward TX-RAMP.
If HQ does not complete at least 40 hours of real admin work a month for you in your first six months (100 hours on Medium), tell us by the end of month five and we refund every dollar you paid for the plan.
The onboarding fee is not refunded. The guarantee asks one thing of you: let HQ do its work. Give it the access it needs and review its work in good faith. If our records show you kept declining or blocking the work HQ set out to do, the guarantee does not apply. If we see that happening, we tell you in writing so you can fix it.
The six months start the day HQ goes live for you. The Founding 50 are included. The guarantee covers HQ only, never coach fees.
What is AI bookkeeping?
AI bookkeeping is AI that does routine finance work: sending invoices, following up on late payments, matching transactions and flagging bills. Shouldered's Finance Desk, run by a Hero named Matthew, does this, and your accountant makes the decisions.
Do I still need my accountant?
Yes. Your accountant decides; Shouldered prepares and tracks so they get cleaner books.
Will it help me get paid faster?
That is the aim.
Where does my data go?
Your private data stays in your own system. Legal, tax, medical and financial decisions stay with you and your licensed advisers; Shouldered prepares and tracks, it never advises.
When can I start?
The Hero is available now. HQ launches in December 2026, and the Founding 50 list is open now for the first 50 companies.
A Christian-run company, and proud of it.
Churches get free Hero seats. When a member's business joins, its church gets an HQ, free.
Simon is named for Simon of Cyrene, who stepped in and shouldered the cross for another. Shouldered takes no outside funding and is open to everyone. The technology comes from the OurWorld group: ten years of work, 60+ engineers, running in 20+ countries.
Pull up a chair.
Start with your Hero today, take a Founding 50 place for HQ, or just come and ask questions in the community.
Founding list
One of the first 50 places. Keep the Founding price as long as you renew.
Hold my place →Your Hero
$25 a seat (Founding price $20). Available now.
Start with your Hero →Telegram
The front door. Talk with us and with owners like you.
Join on Telegram →Or write to Simon: simon@shouldered.com