[Hiring] MassHealth Enrollment Specialist @Pear VC

Role Description

Help patients keep their health coverage — and help us build a better way to do it. BridgeHealthAI is building technology for the healthcare safety net. We work with community health centers to make sure patients don’t lose access to healthcare because of paperwork, missed deadlines, or an impossible-to-navigate system. Our platform helps health centers identify patients who need support, reach them at scale, and automate the administrative work that takes their teams hours today.

We’re a small, fast-moving team building at the intersection of healthcare, AI, and health equity. BridgeHealthAI was born out of Harvard and MIT and is backed by Pear VC, Flare Capital, and Glen Tullman, founder of Livongo. Now, we’re looking for someone who really knows MassHealth.

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.
• Making sure an application actually made it across the finish line.

But this isn’t just an enrollment processing role. You’ll also be the MassHealth expert inside our company. You’ll work directly with our product and operations teams to:

• Show us where patients get stuck.
• Identify what our technology gets wrong.
• Suggest what we could automate or redesign to make the process dramatically easier.

We’re still early, which means there’s a lot to figure out. If you like the idea of doing great work with patients and helping build a better system from the ground up, you’ll probably enjoy this role.

Qualifications

• 3+ years of hands-on MassHealth enrollment, eligibility, or benefits experience.
• Currently or previously a Massachusetts Certified Application Counselor, eligible to be designated again through one of our partner health centers.
• Strong knowledge of MassHealth — eligibility rules, coverage types, renewals, requests for information, the Health Connector, and edge cases.
• Excellent interpersonal skills with patients.
• Ability to manage your own caseload independently.
• Tech-savvy and excited to try new tools.
• Curious about how AI can improve enrollment processes.
• Problem-solving mindset, comfortable in an early-stage startup environment.

Requirements

• Speak Spanish, Haitian Creole, Portuguese, Cape Verdean Creole, or Vietnamese (bonus).
• Experience working at an FQHC, community health center, hospital financial assistance department, or similar safety-net organization (bonus).
• Experience with high-volume renewal campaigns or community enrollment events (bonus).
• Familiarity with Epic, eClinicalWorks, athenahealth, or other health center EHRs (bonus).

Benefits

• Your work has an immediate impact on families keeping access to healthcare.
• Real ownership in a small team environment.
• Your expertise will shape product development.
• Technology designed to make your job easier.
• Opportunity to experiment with new technology.
• Front-row seat in redesigning enrollment and eligibility processes.

The Details

• Part-time: 20–35 hours per week, potential to be extended to a full-time role in the future.
• Compensation: $30–$40/hour.
• Location: Remote, but you must be based in Massachusetts.
• Occasional travel to partner community health centers in Massachusetts.

Interested? Send us your resume and a few sentences about your experience helping people navigate MassHealth. We’d especially love to hear what kinds of enrollment or eligibility cases you’ve worked on, whether you’ve previously been a CAC, and why this work matters to you. And if this role sounds exciting but you don’t check every single box, please apply anyway. We care a lot more about whether you know the work, care about the people we serve, and want to help us build than whether your resume matches every bullet.