Senior Counsel

Pair Team

$205K — $225K *
US-AnywhereRemote in United States
Healthcare
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of healthcare legal experience, particularly with Medicare and Medicaid programs.
  • 3+ years legal experience in a digital health company or managed care organization.
  • Strong understanding of healthcare regulations and technology interactions.
  • Demonstrated adaptability in fast-paced, ambiguous environments, preferably in startup settings.
  • Excellent communication skills for translating complex regulations into actionable guidance.
  • Proven project management skills with ability to prioritize competing demands.

Responsibilities

  • Lead legal advisor on corporate and healthcare regulatory matters.
  • Monitor regulatory changes and offer practical guidance to various teams.
  • Collaborate with teams to ensure legal compliance in operations and clinical care.
  • Draft and negotiate contracts with health plans and service vendors.
  • Provide legal input for Medicaid, Medicare, and commercial strategy development.
  • Identify legal risks and develop compliant solutions proactively.
  • Support litigation and manage outside counsel effectively.

Benefits

  • Remote-first work environment with home office stipend.
  • Flexible PTO and 12 paid holidays.
  • 100% company-paid life, disability, and AD&D insurance.
  • Backup childcare services and financial guidance resources.
  • Equity compensation package.
Full Job Description
About the Opportunity

We're hiring a Senior Legal Counsel to help Pair Team grow and scale responsibly. This is an opportunity to be the second lawyer in the legal department and build inside a fast-moving healthcare company operating at the center of Medicaid and Medicare high needs population care management.

This role reports directly to the Head of Legal.
What You'll Do

Legal & Regulatory Guidance
  • Lead advisor on corporate, healthcare regulatory, litigation, commercial, product, employment, and privacy matters.
  • Monitor regulatory developments and translate their impact into clear, actionable guidance for product, clinical, and operations teams.
  • Collaborate with operational, clinical and marketing leaders to ensure adherence to applicable laws and regulations (e.g. HIPAA, Anti-Kickback, Corporate Practice of Medicine).
  • Understand and provide business friendly guidance on use and impact of artificial intelligence and other technologies in healthcare programs.

Commercial Strategy & Contracting
  • Work on contract development and negotiation-drafting, redlining, and advising on deal terms for health plans, vendors, and partners.
  • Draft templates and playbooks for contracting with partners, including service agreements, BAAs, NDAs, and other agreements..
  • Provide legal and regulatory guidance related to Medicaid, Medicare, value-based care, and product development to support commercial strategy.

Risk Identification & Building Out Legal Function
  • Act as a trusted advisor to business, product, and clinical teams - flagging legal risks early and helping design compliant solutions rather than blocking progress.
  • Help develop legal processes and policies that support risk mitigation, compliance, and business enablement.
  • Effectively manage outside counsel work and spend.

Cross-Functional Collaboration
  • Partner with clinical operations on care delivery compliance, including documentation standards, authorization requirements, and billing compliance.
  • Collaborate with the People team on compliance training, onboarding, and workforce policy development.
  • Support company litigation needs.
  • Represent Pair Team professionally and compliantly in partner, health plan, and regulatory conversations.
  • Other duties as needed.
What You'll Need
  • 5+ years of healthcare legal experience with direct exposure to federal programs (Medicare, Medicaid, or both) and the regulatory frameworks governing them (CMS, OIG, HIPAA, FWA).
  • 3+ years legal experience at a digital health company, health plan, provider, or managed care organization operating in Medicaid and/or Medicare programs.
  • Demonstrated ability to operate in an ambiguous, fast-moving environment - startup or high-growth company experience strongly preferred.
  • Deep working knowledge of the healthcare regulatory environment and practical application to technology products and digital health services.
  • Strong communication skills - able to explain complex regulatory requirements in plain language and make crisp risk/benefit recommendations to business leaders.
  • Ability to multitask, prioritize, and manage projects and tasks.
  • Experience supporting building processes, procedures, and workflows that enable sustainable business scaling.
  • Strong collaboration skills with thought partners from clinical, operations, finance, and leadership
  • Proven ability to prioritize competing demands and make risk-proportionate decisions.
  • Mission-driven and passionate about improving outcomes for underserved communities

Bonus Points for any of the following:
  • Familiarity with value-based care contracts, capitation arrangements, or risk-bearing entities and their compliance implications.
  • Direct experience in pre-litigation and litigation matters and managing outside counsel.
  • Healthcare, privacy, or other relevant certification is a plus.

Our Values
  • Lead with integrity: We keep our commitments and take responsibility for our actions. We are dependable and choose authenticity over perfection.
  • Embrace challenges: We leave our egos at the door and step forward into discomfort instead of back into safety. We help each other to learn and provide feedback using candor and kindness.
  • Break through walls: We go the extra mile for our patients, partners and one another, and we run toward hard things. We are resilient in our push for consistent improvement and challenge the status quo.
  • Act beyond yourself: We build each other up and respect boundaries. We seek first to understand and assume positive intent.
  • Care comes first: We hold ourselves to the highest standards for our patients. We are relentless in the pursuit of our mission, and ensure that we are taking care of ourselves in order to care for others.
Because We Value You
  • Competitive salary: $205,000 - $225,000
  • Equity compensation package
  • Medical, dental & vision with HSA/FSA and company HSA contribution
  • Remote-first with equipment and $100/mo home office stipend
  • Flexible PTO and 12 paid holidays
  • 100% company-paid life, disability & AD&D
  • Backup childcare, caregiver concierge, and financial guidance resources


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