30-min call with RobBook a proof-of-concept call
For owners and the next generation

// AI for family business · Owners and successors

AI for a family business, tested on one job your longest-serving people know best.

For the owner who still signs the checks and knows every customer, the son or daughter who is taking over, and the owner getting a company ready to sell. Choose one desk job your business does every week, ideally one a long-serving employee carries in their head. We run a free AI proof of concept on copies of 20 to 30 documents your team already handled, after an NDA and without logging in to anything, and the person you name as reviewer decides whether it passed.

Book a proof-of-concept call30 minutes with Rob
Family company proof of conceptFree, one job
Scope
One desk job, chosen by the owner
You send
Copies of 20 to 30 finished documents, NDA first
Systems touched
None
Reviewer
Often the person who has done the job longest
Price
A written range first, a fixed price before you sign

// Who this is for

Owners who still know every customer by name

Owners, successors and sellers. This page is for three people in the same kind of company: the owner who still runs it, the next generation stepping in, and the owner preparing a sale. The Census Bureau's Annual Business Survey asks whether two or more members of one family own the majority of a business, and counts spouses, unmarried partners, parents, children, siblings and close relatives as family. Its list of reasons for owning a business includes wanting to carry on the family business. A founder who owns the company alone has the same kind of back office, so the page is written for them too.

The know-how sits with a few long-serving people. The bookkeeper who knows which job every vendor bills against. The estimator who prices from memory. The order desk lead who can read any customer's PO. The Bureau of Labor Statistics reported in September 2026 that median tenure for workers aged 55 to 64 is more than three times that of workers aged 25 to 34, so the person who knows a job best has often been there longest and may be the next to retire. The accounting firm Mauldin & Jenkins writes that family businesses often rely heavily on one individual, and that a casual style favoring gut instinct and trust over written policies can leave internal controls weak.

A succession runs for years. Ritch Sorenson, who holds the Opus endowed chair in family business at the University of St. Thomas, told FamilyBusiness.org that the rule of thumb is at least ten years to plan for succession. Ownership, leadership and the family's own decisions belong with your advisers. A desk job is a smaller question with an answer you can check: a test on one of them shows how much of it can be drafted from past work, while the person who knows it is still there to judge.

A buyer rewrites the family's numbers. In a sale, the buyer's quality of earnings review recasts the company's earnings. The Bonadio Group lists family members on the payroll who don't work for the company among the costs it takes out of adjusted EBITDA, restates the owner's pay to the market rate for the role, and adjusts rent paid to an owner's property company as if it had been paid at arm's length. We do none of that work. Those adjustments are one reason a buyer asks which family members actually work in the business, and what each of them does.

Key people get a close look. In an article on the National Law Review, S. Graham Simmons III of Norris McLaughlin says buyers look closely at all key employees, especially those related to the owner, and ask whether they are critical to running the business, whether they are legacy hires and whether they will stay after the sale. A job only one person can do will come up in that conversation. A test can't settle it, but it gives the owner a scored answer, early and in private, on whether one such job can be drafted from the documents it leaves behind.

// Jobs that fit

Desk jobs one long-time person carries

One job at a time
Judged by your own person
01 · QUOTING

Quotes priced from one estimator's memory

The estimate only one long-time person knows how to price. Drafts are built from quotes your company already sent and rates it already charged, then checked by that estimator against what went out.

Compare the quoting desks
02 · ORDER DESK

Customer POs only one person can read

The buyer who sends a marked-up PDF, the customer with its own part numbers. POs your desk already entered are drafted as sales orders, and the person who entered them checks every line.

See sales order automation
03 · PAYABLES

Vendor bills the bookkeeper codes by heart

Invoices placed on the job, property, PO line or project phase they belong to, the way your bookkeeper would, and scored against how they were actually posted.

See AP automation by industry
04 · MONTH-END

The numbers the owner reads every month

For manufacturers. The monthly package drafted from ERP exports for months already closed, so the controller who builds it by hand can check each figure against the one they sent.

Open the month-end page
05 · ORDER STATUS

Where is my order, answered from the records

For make-to-order plants where the answer waits on the one person who can walk the floor. Status replies are drafted from the order line, the job and the shipment, and say only what those records show.

Open the order status page
06 · RECEIVABLES

Customers the owner knows by name

For distributors. Past-due follow-ups drafted from a copy of the aging report, with the paperwork each invoice needs, for whoever knows those customers best to approve one at a time.

Open the collections page

// Who judges

Why the person who has done the job longest is the reviewer

What they know is the answer key. Your reviewer lays our drafts beside what they and the team actually did on the same documents. When a draft misses something only they would catch, such as a customer's habit or a vendor that always bills to the wrong job, it shows up as a miss on the scorecard. They don't have to write anything down first; their past work is the test.

Built around them, not instead of them. The test only drafts. If it passes and the job goes live, a person approves every item before it posts anywhere, and the natural choice for that is the person who judged the test. Nothing in it asks you to change who does the work or how long they stay.

The circle stays small. Some owners would rather keep a test between a few people until there is something to decide. Because it runs on copies and needs no logins, it can stay between the owner, the reviewer and us, under an NDA signed before any document moves. If the documents can't leave the building, we build look-alikes with the reviewer instead.

// How it runs

Four steps, decided by your own people

NDA first
No logins
  1. Step 01

    Choose the job

    The owner, or the next generation with the owner's agreement, picks one desk job. A good first choice is the one that would stall if a certain person took a month off.

  2. Step 02

    Name the reviewer

    The owner names the reviewer, usually the person who has done that job for years. Together we write down the success criteria, and you get a price range for running the job live before anything starts.

  3. Step 03

    Sign the NDA, then send copies

    Once the NDA is signed, the company sends copies of 20 to 30 finished documents from that job. We don't connect to your accounting system, your ERP or your email. Look-alikes are an option if the originals have to stay put.

  4. Step 04

    Compare, then about 30 days live

    Your reviewer checks each draft against what the team did with the same document. After a yes, the job runs live for about 30 days with a person approving every item. A second job is a separate decision with its own price.

// One hard limit

No estate, tax or succession advice.

We don't advise on who should take over, what the company is worth, how a sale is structured, or anything to do with wills, trusts, gifting or taxes. Those belong to your attorney, your CPA and your other advisers. We also never replace a person: the test covers one desk job on copies of past documents, and the reviewer you name stays the judge, during the test and after the job goes live.

Priced per job. You get a range before the proof of concept and a fixed price before you sign.

What the live job costs depends on how many of those documents arrive in a month and which systems it has to reach. Support is billed monthly once it runs, and any further job is quoted separately.

// Questions

What family owners ask

Will this put long-time employees out of a job?
That is not what it is for. The test only drafts, and the person who has done the job for years is the one who judges it. If it goes live, a person on your team approves each item before it posts, and who does the work stays your decision.
Can we keep this quiet, inside the family and with staff?
Yes. An NDA is signed before any document moves, the test runs on copies, and nothing logs in to your systems, so only the people you tell need to know. If you'd rather nothing leave the building, we build look-alike documents with your reviewer.
What does it cost?
The proof of concept is free. Before it starts you get a written price range for running that job live, and a fixed price before you sign anything. Each later job is priced on its own, with monthly support once a job is running.
What if it doesn't work?
Then you find out on old documents, with nothing bought and nothing connected. Your reviewer scores the drafts against success criteria agreed beforehand, and if they say it failed, it failed. There is nothing to undo, because nothing touched your systems.
We may sell in a few years. Does this help with a buyer?
We can't tell you how a buyer will view it, and we don't advise on sales or valuation; that is for your M&A adviser and your CPA. What the test gives you is a scored answer on one job, judged by your own person, on your own past documents. What you do with that answer is up to you and your advisers.
The founder still runs the company. Can the next generation start this?
Yes, though the owner should agree before any documents move, because the company signs the NDA and the owner names the reviewer. If it is easier, bring both generations to the same first call. The test then runs the same way whoever booked it.
Rob Eason

Rob Eason, founder

// Book a proof-of-concept call

Bring the job that depends on one person.

A 30-minute call with Rob. Tell him your role in the company, the job you'd test, who does it today, and roughly how many of those documents come in each month. Please hold back every file until the NDA is signed.

  • Co-owned a 60-employee financial services firm and sold his share to his partner.
  • Ran GOSO Technologies, a Boston solar company rated 5/5 across 24 Google reviews.
  • 5/5 across 83 reviews in HighLevel's Certified Admin Directory.
  • 4.3/5 from 6 Google reviews of Massmarket AI.
  • Every directory and Google review, critical ones included, is shown word for word at massmarket.ai/reviews.
  • Takes every proof-of-concept call himself.