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MassHealth Enrollment Specialist & AI Operations

OodleBostonBridge Health AI
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Salary
$50K – $70K
Job type
Part-time
Work mode
Remote
Posted
9 Sept 2026
Status
Open · checked 9d ago

About this role

Role Overview

The MassHealth Enrollment Specialist & AI Operations position at Frontdesk AI is a part-time, remote role based in Massachusetts that involves helping patients maintain healthcare coverage while collaborating with product teams to improve enrollment technology. This opportunity is well-suited for a healthcare professional with deep MassHealth expertise who wants to combine direct patient advocacy with innovative artificial intelligence operations.

Key Responsibilities

Connect one-on-one with MassHealth members via phone and video to finalize applications, manage renewals, collect required documents, and resolve eligibility challenges.
Take full ownership of individual patient cases from initiation to resolution rather than performing single-interaction handoffs.
Back renewal initiatives across multiple community health center partners.
Assist patients in interpreting complex MassHealth and Health Connector notifications, communicating with customer service on their behalf when necessary.
Maintain communication with health center teams and appropriately escalate highly complex cases.
Identify recurring patterns where patients experience bottlenecks and share these actionable insights directly with the product development team.
Evaluate patient communication materials, scripts, and workflows to ensure they accurately reflect real-world enrollment procedures.
Contribute to building operational playbooks for delivering enrollment support as the organization expands.

Requirements

Minimum of three years of practical, hands-on experience with MassHealth enrollment, eligibility determinations, or benefits navigation.
Current or prior status as a Massachusetts Certified Application Counselor with eligibility for redesignation through a partner health center.
Comprehensive knowledge of MassHealth regulations, coverage categories, renewal processes, information requests, the Health Connector, and associated edge cases.
Exceptional interpersonal skills with patients, making stressful or intricate processes manageable and clear.\- Detail-oriented mindset capable of catching missing verifications or incomplete submissions proactively.
Ability to independently manage a caseload and follow through on tasks autonomously.
Tech-savviness, curiosity regarding artificial intelligence applications in enrollment, and comfort experimenting with emerging tools.
Comfort working in an early-stage startup environment where structured step-by-step playbooks are actively being developed.

Nice to Have

Fluency in Spanish, Haitian Creole, Portuguese, Cape Verdean Creole, or Vietnamese.
Professional background at an FQHC, community health center, hospital financial assistance division, or comparable safety-net organization.
Experience managing high-volume renewal drives or community enrollment initiatives.
Familiarity with electronic health record systems such as Epic, eClinicalWorks, or athenahealth.

Skills and Tools

MassHealth Eligibility and Enrollment Rules
Health Connector Navigation
Certified Application Counselor (CAC) Expertise
Patient Advocacy and Communication
Case Management
AI Operations and Workflow Optimization
Electronic Health Records (Epic, eClinicalWorks, athenahealth)

Salary and Benefits

Annual compensation ranging from $50,000 to $70,000.
Minimum of 40 hours per week with the potential for extension into a full-time position.
Remote work flexibility within Massachusetts.

About the Company

Frontdesk AI, operating through Bridge Health AI, builds technology dedicated to the healthcare safety net. The organization collaborates with community health centers to prevent patients from losing healthcare access due to administrative hurdles, missed deadlines, or complicated systems. Born out of Harvard and MIT, the company is backed by prominent investors including Pear VC, Flare Capital, and Livongo founder Glen Tullman.

How to Apply

Apply on the official company careers page by submitting a resume and a brief statement detailing your experience helping individuals navigate MassHealth, including your background with enrollment cases, previous CAC status, and motivation for this work.

Questions candidates ask

What is the location requirement for this remote job?

While the role is remote, candidates must be based in Massachusetts and be eligible to be designated as a Massachusetts Certified Application Counselor.

What is the compensation for this position?

The salary ranges from $50,000 to $70,000 per year for a minimum of 40 hours per week.

How much experience is required?

Candidates must have 3+ years of hands-on MassHealth enrollment, eligibility, or benefits experience.

What background is helpful for this role?

Experience working at an FQHC, community health center, hospital financial assistance department, or safety-net organization is a plus, as is multilingual fluency in languages such as Spanish, Portuguese, or Haitian Creole.

How can I apply?

Interested candidates should apply on the official company careers page by sending a resume and a short description of their MassHealth experience.

Ready to apply?

The application is on the official Oodle careers page.

Apply on company site