The Thrills, the Chills & the Pitfalls · monthly

How to Finance Your Team's AI Training

Most small businesses treat AI training as a cost they carry alone. In Massachusetts it is often reimbursable, and in many other states it is too. One hour on how to get your team trained without paying for all of it yourself.

Tuesday, October 27, 2026
12:30 – 1:30 PM ET
Virtual via Google Meet
Free · one hour · live Q&A
Register — it's free
Cartoon: a worried purple small-business owner holds a long AI training receipt while a golden-domed State House in sunglasses gives a thumbs-up and stamps it.
Plot twist: in Massachusetts, the state can pick up the tab. We'll show you how.

What we'll cover

Program rules change, so we confirm current terms live in the session.

1

The Workforce Training Fund Express Program

For Massachusetts employers with up to 100 W-2 employees in the state: up to 100% of the training cost reimbursed, up to $3,000 per person per course and $15,000 per company per year, for courses from a registered training provider.

2

The General Program, for bigger plans

Grants from $10,000 to $200,000 for larger or longer training efforts, matched one-to-one by the employer. The time your people spend in training can count toward your match.

3

The rules that trip people up

Apply before training starts (at least 21 days ahead for Express), what counts as eligible training and what does not, and the paperwork to have ready, including your Certificate of Good Standing and W-9.

4

Outside Massachusetts, and building the budget

How other states compare, and how to plan AI training so it pays for itself even when no grant applies. Bring your questions; the last part of the hour is open Q&A.

Outside Massachusetts? See what your state reimburses →

The series

The Thrills, the Chills & the Pitfalls

One hour, one topic, live Q&A, every month. What actually happens when small and mid-sized businesses put AI to work: the wins, the surprises, and the mistakes worth avoiding. Free to attend.

Host

Perry Bailes

Founder & Principal Consultant, Support Forge LLC

Perry helps small and mid-sized businesses put AI to work and train their teams to run it, across healthcare, legal, manufacturing, construction, finance, and professional services.

Reserve your spot

Free to attend. Register and we'll email you the Google Meet link.

Free to attend. By registering, you agree to be contacted by Support Forge about this event.