This is a full-time U.S. remote OR a hybrid position based in the Fort Lauderdale, FL area.

MASA is looking for a hands-on contracts attorney who sees AI as a core part of how modern legal work gets done. You’ll manage day-to-day contracting for the company, use AI-enabled legal tools on real agreements every day, and help the General Counsel shape how the Legal Department adopts AI responsibly. If you’d rather be the lawyer building the AI-powered workflow than the one skeptical of it, this is your seat.

About Us

MASA has been a leader in emergency medical transportation insurance since 1974. We're not just a company – we're a close-knit team dedicated to "Protecting families with compassion when others don't." Our professional yet friendly company culture fosters collaboration, innovation, and a clear mission that resonates through every role as we support our expanding base of 2+ million members across the United States and the Caribbean. Learn more at https://www.masaaccess.com

What You Will Do

Reporting to our General Counsel as Counsel, Contracts & Legal Operations, you will:

• Own the full agreement lifecycle: drafting, negotiating, and managing vendor, technology/SaaS, data-processing, licensing, provider/network, consulting, and marketing agreements from intake through signature, repository, and renewal, with AI built into how you work.
• Put AI to work across the contract portfolio, using AI-enabled legal tools to analyze terms, compare drafts, spot issues, summarize obligations, and triage risk, while validating every output with your own independent legal judgment.
• Help shape how MASA governs AI in legal work, setting practical guardrails that protect privilege, confidentiality, personal data, and PHI as our use of these tools grows.
• Apply healthcare and insurance expertise, advising on HIPAA, Business Associate Agreements, privacy, and data security, and translating contract terms into clear business exposure, risk analyses, and Executive Summaries for the right reviewers and signers.
• Build and continuously improve the contracting function, using AI and workflow technology to power intake, triage, templates, playbooks, dashboards, and self-service tools that make compliant contracting easy across MASA.
• Train stakeholders, report on performance, and collaborate across the company, leading training on the Contract Review Management SOP, delivering monthly KPI reporting to the General Counsel, partnering with Finance, Procurement, Information Security, Privacy, Compliance, and HR, supporting IP and marketing review, and managing outside counsel when needed.

What You Bring

• J.D. from an accredited law school and active, good-standing bar membership.
• At least 3 years of progressively responsible legal experience, with substantial in-house responsibility for commercial contracts.
• Demonstrated healthcare and/or insurance experience, including negotiating Business Associate Agreements and advising on HIPAA, privacy, and security requirements.
• A strong track record of independently drafting and negotiating complex commercial agreements and explaining risk to senior stakeholders.
• Genuine enthusiasm for AI and hands-on experience using AI-enabled contract or legal tools for issue spotting, comparison, summarization, obligation extraction, or risk analysis, with disciplined validation and strong confidentiality controls.
• Experience improving a contract-review or lifecycle process through AI, templates, playbooks, or workflow technology, and the ability to work independently in a lean legal department supporting multiple business units; experience with CLM systems, Docusign workflows, IP portfolio work, or marketing/insurance review is a plus.

What We Will Provide You

• Competitive base salary, bonuses, and comprehensive employee benefits programs, including medical, dental, and vision insurance with highly rated carriers; a 401(k) program with a company match; paid time off; company-paid short-term disability, long-term disability, and basic life insurance; and a free MASA membership.
• A professional and friendly company culture that supports a clear mission: "Protecting families with compassion when others don’t."
• Real room to put AI to work: the chance to use AI-enabled legal tools in your daily practice and help shape how MASA’s Legal Department adopts them responsibly.

Why We Think You’ll Love This Opportunity

If AI energizes you rather than worries you, you’ll fit right in. You’ll use AI-enabled tools on real contract work every day, help set the standards for using them responsibly, and see the impact on the quality and speed of how MASA contracts. It’s a chance to show what a modern, AI-forward legal department can do, as a key partner to the General Counsel while the department grows.

NOTE: Any pay range listed for this position is an estimate by the job board and may not reflect the actual compensation.

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