MassHealth Enrollment Specialist & AI Operations

Pear VC; Boston (MA); On-site; USD 50,000 - 70,000; Full time

Job summary

BridgeHealthAI is seeking a MassHealth Enrollment Specialist to help patients keep coverage and to inform product development. You’ll guide members through renewals, explain notices, and collect documents, while acting as the MassHealth expert inside the company.

You’ll collaborate with product and operations to simplify enrollment and reduce administrative burden. This remote, Massachusetts-based role offers ownership of cases, direct patient interaction, and a path toward building scalable

Qualifications

• 3+ years of hands-on MassHealth enrollment, eligibility, or benefits experience.
• MassHealth knowledge: eligibility rules, coverage types, renewals, Health Connector.
• Ability to explain complex enrollment steps clearly to patients.
• Experience managing a personal caseload and following through.
• Comfort with new tools and AI-enabled workflows.

Responsibilities

• 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 handing them off after one interaction.
• Support renewal campaigns across several community health center partners.
• Help patients understand MassHealth notices and work with customer service when needed.
• Keep health center teams in the loop and escalate genuinely complicated cases.
• Spot patterns in where patients get stuck and share insights with the product team.
• Review outreach, scripts, and workflows and suggest improvements reflecting real-world enrollment.
• Help build the playbook for BridgeHealthAI enrollment support as we grow.

Skills

MassHealth enrollment experience

Eligibility knowledge

Patient communication

Caseload management

Tech-savvy

Job description

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 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.

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 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, what our technology gets wrong, and 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.

What You’ll 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 escape 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 doesn’t reflect how enrollment works in the real world.

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

You’ll 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.

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

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

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

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

• You like figuring things out. We’re an early-stage startup, so not every process will come with a perfect step-by-step playbook — sometimes we’ll build it together.

Bonus Points

We’d 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. You’ll directly help families keep access to healthcare.

You’ll have real ownership. We’re a small team. You won’t be several layers removed from decisions or from the people building the product.

Your expertise will shape what we build. We aren’t 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. We’re actively building tools to remove repetitive administrative work so you can spend more of your time actually helping patients.

You’ll get to experiment with new technology. We’re actively exploring how AI, automation, and better workflows can fundamentally change enrollment work. You’ll be one of the people helping us figure out what works and what doesn’t.

You’ll help us build something new. We believe a huge amount of enrollment and eligibility work can be redesigned, and you’ll 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