6 Steps to Train 5 Employees in AI With Up to $15,000 Reimbursed

Massachusetts employers with 100 or fewer Massachusetts W-2 employees can train five people in AI through the Workforce Training Fund Express Program in six steps: confirm eligibility, pull three documents, pick the course and trainees, apply at least 21 days before the start, train on paid time, then pay and claim reimbursement of up to $15,000.

Quick facts

• Tuition: 5 seats x $3,000 = $15,000, which equals the Express cap of $15,000 per company per calendar year.
• Reimbursement: up to 100% of the course cost, if approved. You pay first and are reimbursed afterward.
• Course format: live, instructor-led, 10 instructional hours over 4 to 5 weeks.
• Filing deadline: at least 21 days before the course start date.
• Your cost either way: regular wages for each trainee during the 10 training hours.
• Application help is free, and the employer files the application.

The Express Program is part of the Workforce Training Fund Program, a Massachusetts state program administered by Commonwealth Corporation. Massachusetts employers pay into the fund through their unemployment insurance contributions. Our Massachusetts AI training grants page has the overview. This post is the timeline.

The honest math. Five seats at $3,000 each is $15,000 in tuition. That is exactly the annual Express cap, so up to $15,000 can come back if the application is approved. Approval is never guaranteed. You pay the $15,000 first. And the wages you pay five people during their 10 hours of class, 50 paid hours in total, are your cost and are not reimbursed.

1. Confirm the six eligibility points

Check these first. If one fails, Express does not fit.

1. Headcount. You have 100 or fewer Massachusetts W-2 employees.
2. Location. You have a physical Massachusetts location, owned or leased.
3. Trainees. The people you want to train are W-2 payroll employees, full or part time, who work in Massachusetts. Owners, 1099 contractors and temp workers cannot be counted.
4. Course. The course is listed in the state's Express Course Directory. Legally mandated training, such as OSHA, does not qualify.
5. No repeats. None of the trainees has taken the same or similar WTFP-funded training in the past five years.
6. Paid time. You will pay trainees their regular wages during training hours.

The rules are the same across the state. We keep local pages for employers who want the city view, including AI training grants in Quincy and AI training grants in Framingham.

2. Pull the three documents and check their dates

The Express application requires three documents:

• A Certificate of Good Standing from the Department of Revenue, dated within 6 months.
• A current Certificate of Compliance from the Department of Unemployment Assistance.
• A Form W-9, dated within 1 year.

You may already have copies on file. Old copies are the problem. If the Certificate of Good Standing is older than 6 months or the W-9 is older than 1 year, get a new one before you file. Do this step early, so a stale document does not push back your filing date.

3. Pick the course and the five W-2 employees

We offer five AI courses through our training partner, a registered Express Program training provider. Each is live, instructor-led, 10 instructional hours and $3,000 per trainee:

• AI Enablement for Small Business Teams: 2 hours x 5 weeks, up to 8 trainees
• Claude Code for Operations and Data Teams: 2.5 hours x 4 weeks, up to 6 trainees
• AI for Finance, Accounting and Payroll Teams: 2 hours x 5 weeks, up to 8 trainees
• AI for Field Service and Trades Businesses: 2 hours x 5 weeks, up to 8 trainees
• AI for Professional Practices: 2 hours x 5 weeks, up to 8 trainees

Why five people? Five seats at $3,000 uses the full $15,000 cap for the calendar year. A sixth seat in the same year goes past the cap, so plan to pay for that one yourself.

Pick the five who will use the skills every week. Confirm each one is on W-2 payroll and works in Massachusetts. Leave the owner off the trainee list.

4. File the Express application at least 21 days before the start date

The employer applies online, at least 21 days before the course start date. Work backward. Pick the start date, count back 21 days, and treat that as the last possible filing day. Then file earlier than that.

Two more timing rules apply. The course must start within 6 months of the application, and training must be finished within 12 months.

You file the application, not the provider. Training providers are not allowed to charge for application help, so help with the application is free. Commonwealth Corporation decides on approval. The official Workforce Training Fund Program page is the source for current guidelines.

5. Run the 10 hours of live training on paid time over 4 to 5 weeks

Four of the five courses run 2 hours a week for 5 weeks. The Claude Code course runs 2.5 hours a week for 4 weeks. Either way, each trainee gets 10 instructional hours.

Employees must be paid their regular wages during training hours, and live virtual training has to happen on paid time. Put the sessions on the calendar as work, inside the normal workday. Do not move them to evenings off the clock.

Keep your own attendance record as you go. You will need a trainee list at reimbursement time.

6. Pay the invoice, then submit for reimbursement

You pay the provider's invoice for the course first. Then you submit for reimbursement with three items:

• The provider invoice, matching the approved course name.
• Proof of payment.
• The trainee list.

The Commonwealth reimburses the employer. We do not quote a number of days for that, so plan your cash as if the $15,000 is out the door until it comes back.

Keep the invoice clean. The grant does not pay for consulting, coaching, software subscriptions, exam or certification fees or travel. Work applying the training to your own systems is not covered either, so keep it on a separate invoice.

Questions we get

How do I apply for Workforce Training Fund Express?

The employer applies online at least 21 days before the course start date. You need a Certificate of Good Standing from the Department of Revenue dated within 6 months, a current Certificate of Compliance from the Department of Unemployment Assistance and a Form W-9 dated within 1 year. The course must be listed in the state's Express Course Directory.

Is the Massachusetts AI training grant free money for a small business?

No. The Express Program is a reimbursement. The employer pays for the course first, then submits the provider invoice, proof of payment and trainee list. The Commonwealth reimburses up to 100% of the course cost, within caps of $3,000 per employee per course and $15,000 per company per calendar year, if approved. Trainee wages are not reimbursed.

Can the business owner be one of the five trainees?

No. In the Workforce Training Fund Express Program, trainees must be W-2 payroll employees, full or part time, who work in Massachusetts. Owners, 1099 contractors and temp workers cannot be counted as trainees. An employee also cannot repeat the same or similar WTFP-funded training within five years, so check each person's training history before you file.

Start with a 15 minute eligibility call

If you want to run this timeline, book a 15 minute eligibility call through the form on our Massachusetts grant page. We cover the six eligibility points, the three documents and a start date. Help with the application is free. You, the employer, file the application, and approval is decided by Commonwealth Corporation.

Training is half of an AI rollout. The other half is building the workflows inside your own systems, which the grant does not pay for. JMK's separate free AI audit maps that side at no cost, so your five trained employees have something real to work on when the course ends.

Program terms verified against Commonwealth Corporation's published guidelines on September 21, 2026. JMK Ventures is not affiliated with or endorsed by Commonwealth Corporation.