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MassHealth Enrollment Specialist & AI Operations

Pear VC


Job Location:

Boston, NH - USA

Yearly Salary: USD 50000 - 70000
Posted: 29 September 2026 (2 days ago)
Application Deadline: 27 December 2026
Vacancies: 1 Vacancy

Job Summary

MassHealth Enrollment Specialist & AI Operations

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 dont 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.

Were 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 were looking for someone who really knows MassHealth.

The Role

Our technology can identify a patient who is at risk of losing coverage reach them and figure out where theyre getting stuck.

Youll 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 made it across the finish line.

But this isnt just an enrollment processing role.

Youll also be the MassHealth expert inside our company. Youll work directly with our product and operations teams to show us where patients get stuck what our technology gets wrong and what we could automate or redesign to make the process dramatically easier.

Were still early which means theres 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 youll probably enjoy this role.

What Youll Actually Do
  • Work one-on-one with MassHealth members by phone and video to complete applications and renewals gather documents respond to requests for information and resolve eligibility issues.

  • Own patient cases from start to finish rather than simply handing them off after one interaction.

  • Support renewal campaigns across several of our community health center partners.

  • Help patients understand confusing MassHealth and Health Connector notices and work with customer service on their behalf when needed.

  • Keep health center teams in the loop and escalate the genuinely complicated cases.

  • Spot patterns in where patients are getting stuck and bring those insights directly to our product team.

  • Review patient outreach scripts and workflows and tell us when something doesnt reflect how enrollment works in the real world.

  • Help us build the playbook for how BridgeHealthAI delivers enrollment support as we grow.

Youll Probably Be Great at This If...
  • You have 3 years of hands-on MassHealth enrollment eligibility or benefits experience.

  • You are currently or were previously a Massachusetts Certified Application Counselor and are eligible to be designated again through one of our partner health centers.

  • You know MassHealth well eligibility rules coverage types renewals requests for information the Health Connector and all the weird edge cases that come with them.

  • Youre great with patients. You can make a complicated or stressful process feel understandable and manageable.

  • Youre the person who catches the missing verification or incomplete application before it turns into a bigger problem.

  • Youre comfortable managing your own caseload and following things through without someone checking on you every day.

  • Youre tech-savvy and excited to try new tools. Youre curious about how AI can make enrollment work faster and easier and youre energized by experimenting with new technology rather than intimidated by it.

  • You like figuring things out. Were an early-stage startup so not every process will come with a perfect step-by-step playbook sometimes well build it together.

Bonus Points

Wed be especially excited if you:

  • Speak Spanish Haitian Creole Portuguese Cape Verdean Creole or Vietnamese.

  • Have worked at an FQHC community health center hospital financial assistance department or similar safety-net organization.

  • Have experience with high-volume renewal campaigns or community enrollment events.

  • Have worked with Epic eClinicalWorks athenahealth or other health center EHRs.

None of these are dealbreakers.

Why BridgeHealthAI

Your work has an immediate impact. Youll directly help families keep access to healthcare.

Youll have real ownership. Were a small team. You wont be several layers removed from decisions or from the people building the product.

Your expertise will shape what we build. We arent hiring you just to process renewals. We want you to teach us how to make the entire process better.

Technology should make your job easier not harder. Were actively building tools to remove repetitive administrative work so you can spend more of your time actually helping patients.

Youll get to experiment with new technology. Were actively exploring how AI automation and better workflows can fundamentally change enrollment work. Youll be one of the people helping us figure out what works and what doesnt.

Youll help us build something new. We believe a huge amount of enrollment and eligibility work can be redesigned and youll have a front-row seat in figuring out what that looks like.

The Details
  • Full Time: Minimum 40 hours per week potential to be extended to a full-time role in the future

  • Compensation: $50k to 70k a year

  • Location: Remote but you must be based in Massachusetts

  • Travel: 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.

Wed especially love to hear what kinds of enrollment or eligibility cases youve worked on whether youve previously been a CAC and why this work matters to you.

And if this role sounds exciting but you dont 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.


Required Experience:

IC


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