MassHealth Enrollment Specialist

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🔥 0 minutes ago

🍂 Massachusetts – Remote

🍂 Massachusetts – Remote

💵 $30 - $40 / hour

⏱ Part Time

🟡 Mid-level

🟠 Senior

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Pear VC

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2013

💼 Consulting

📣 Marketing

🤖 Artificial Intelligence

Consulting • Marketing • Artificial Intelligence

Pear VC is an early-stage venture capital firm specializing in pre-seed and seed investments that pairs capital with hands-on founder support. The firm—made up of founders-and-operators turned investors—runs programs like PearX, provides in-house recruiting and talent services, go-to-market and fundraising coaching, PR and marketing support, and physical workspaces (Pear Studio). Pear emphasizes community and tailored resources for diverse founders and has a notable focus on supporting AI and biotech startups through grants, events, and sector-specific playbooks.

📋 Description

• 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 • Support renewal campaigns across community health center partners • Explain MassHealth and Health Connector notices and work with customer service on patients’ behalf • Keep health center teams informed and escalate complicated cases • Identify patterns in patient challenges and share insights with the product team • Review patient outreach, scripts, and workflows for alignment with real-world enrollment processes • Help build BridgeHealthAI’s enrollment-support playbook as the company grows

🎯 Requirements

• 3+ years of hands-on MassHealth enrollment, eligibility, or benefits experience • Currently or previously a Massachusetts Certified Application Counselor and eligible to be designated again through a partner health center • Knowledge of MassHealth eligibility rules, coverage types, renewals, requests for information, Health Connector processes, and edge cases • Ability to support patients through complicated or stressful processes • Ability to identify missing verification or incomplete applications • Comfortable independently managing a caseload and following cases through to completion • Tech-savvy and willing to try new tools and AI-enabled technology • Ability to work effectively in an early-stage startup with evolving processes • Must be based in Massachusetts • Must be eligible to work in the United States; visa sponsorship requirements are addressed in the application form

🏖️ Benefits

• Potential to be extended to a full-time role in the future • Real ownership and direct access to decisions and product builders • Opportunity for expertise to shape the product • Technology and tools intended to reduce repetitive administrative work • Opportunity to experiment with AI, automation, and new workflows • Opportunity to help build a new enrollment-support system