MassHealth Enrollment Specialist & AI Operations is open at Pear VC in Boston (remote). The posting gives a salary of $50K - $70K. Posted on Sep 9, 2026, and still on Pear VC’s careers page when we last checked, on Nov 14, 2026.
About the role
Our technology can identify a patient who is at risk of losing coverage, reach them, and figure out where they’re getting stuck. You’ll help take them the rest of the way. That might mean getting on the phone with a patient to complete their renewal, figuring out what a confusing MassHealth notice actually means, tracking down a missing document, calling MassHealth with them, or making sure an application actually…
The opening lines of the posting. The rest is on Pear VC’s careers page.
Hiring at Pear VC
Pear VC has 107 open roles right now, 17 of them remote. Most are in Engineering, Sales & Business Development and Operations. The median advertised salary across its roles with a published range is $170K. See all its roles