MassHealth Enrollment Specialist

Pear VC, Inc.

Job Overview

Location

Boston

Job Type

Part-time

Full Job Description

📋 Description

• Help patients keep their health coverage by working 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 doesn’t reflect how enrollment works in the real world.
• Help us build the playbook for how BridgeHealthAI delivers enrollment support as we grow.

🎯 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 one of our partner health centers.
• MassHealth expertise, including eligibility rules, coverage types, renewals, requests for information, the Health Connector, and all the weird edge cases that come with them.
• Excellent communication and interpersonal skills.
• Ability to manage own caseload and follow things through without someone checking on you every day.
• Tech-savvy and excited to try new tools.

🏖️ Benefits

• Competitive hourly rate of $30–$40/hour.
• Part-time role with 20–35 hours per week, potential to be extended to a full-time role in the future.
• Opportunity to work with a small, fast-moving team building at the intersection of healthcare, AI, and health equity.
• Real ownership and impact, with the ability to shape what we build and make the entire process better.
• Occasional travel to partner community health centers in Massachusetts.

Skills & Technologies

REST

Remote

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Pear VC, Inc.

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About Pear VC, Inc.

Pear VC is an early-stage venture capital firm founded in 2013 and based in San Francisco. It invests pre-seed and seed capital in enterprise software, consumer, fintech, healthcare, and deep-tech startups. The firm provides founders with a full-time, in-house product, design, and growth team during the company-building phase. Pear manages over $1.8 billion across multiple funds and has backed companies such as DoorDash, Guardant Health, Gusto, and Branch. The partnership emphasizes hands-on support, data-driven insights, and a tight-knit community to accelerate product-market fit and subsequent fundraising.

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