How to Finance Your Team's AI Training: October Session Recap

On October 27, we ran the first Thrills, the Chills & the Pitfalls session, our free monthly hour on putting AI to work. The topic was the one we get asked about most: how a small or mid-sized business gets its team's AI training paid for. Thanks to Joe Khoury for co-presenting.

Here is the breakdown, whether you made it live or not.

The two programs that pay

Massachusetts runs one fund, the Workforce Training Fund, with two ways in.

Express grants are for companies with 100 or fewer Massachusetts W-2 employees.

• Covers up to 100% of an approved course
• Up to $3,000 per person per course, and $15,000 per company per year
• The course has to come from the state's pre-registered Express course directory

General grants are for bigger or longer training plans, at employers of any size that contribute to the Fund.

• Requests from $10,000 to $200,000
• Requires a 1:1 match from the company, and the wages you pay people during training hours count toward that match

The rules that trip people up

• Apply before training starts. For Express, the agreement start date is set 21 days after you submit, so the clock starts with your application, not your first class. General decisions generally take up to 60 days, so apply well ahead.
• Past training doesn't count. Both programs fund training that hasn't happened yet.
• Have the paperwork ready. Express asks for a DOR Certificate of Good Standing (dated within the last six months), a DUA Certificate of Compliance and a W-9.
• The state decides. Eligibility and award decisions are made by the Commonwealth, not by any training provider.

Fun facts most employers haven't heard

• The rate doubled this spring. Until April 1, 2026, Express paid companies with 51 to 100 Massachusetts employees 50% of the course cost. It now pays 100%, up to $3,000 per person per course.
• The General cap went up too. On the same date it rose from $125,000 to $200,000, and employers can now use Express and General at the same time.
• There's an hourly ceiling. Both programs cap reimbursement at $300 per hour of instruction, so a long course doesn't automatically mean a bigger check.
• Some things never qualify. The General Program won't fund consulting, coaching, tuition reimbursement or one-on-one training.
• Free AI certificates exist for everyone in the state. Through the Massachusetts AI Hub, any Massachusetts resident can take Google's AI certificates at no cost through December 31, 2027. They're self-paced, which is exactly the kind of training Express won't reimburse, so the two fit together.
• Apprenticeships got an AI hook. The Registered Apprenticeship Tax Credit is worth 50% of an apprentice's wages, up to $4,800 per apprentice per year, and 2026 eligibility now includes occupations with AI-related credentials. For tax year 2025, the state approved $988,800 in credits across 206 apprentices, double the year before.

Program figures were verified against Commonwealth Corporation's published guidelines; caps move with available funding, so check the current terms before you apply.

Where to start

Our five live AI courses are approved for the Express program. See how the grants work, or check which program fits your state and team size. If you'd like help working out whether your team qualifies, book 30 minutes.

Next session

The next monthly session is in November. Details and registration will be at the same link: support-forge.com/events/monthly. What should we cover? Reply to any of our emails with the AI question your team is stuck on, and we'll build a session around the most common ones.