About the position

We're looking for a practical, business-minded attorney to join Amwell's Legal team as Senior Legal Counsel. The heart of this role is federal commercial contracting and compliance—you'll be our go-to person for prime contracts, subcontracts, flow-down requirements, and the program compliance obligations that come with doing business with the government. From that foundation, you'll also get plenty of variety: supporting clinical contracting and lending a hand on employment, privacy, regulatory, and litigation matters as they come up. If you enjoy being close to the business, like the mix of deep specialty work and broad generalist support, and get satisfaction from being the person teams turn to for a clear, sensible answer, you'll feel right at home here. You'll partner with colleagues across Sales, HR, Clinical, Finance, Operations, and Compliance. We care about your judgment, your curiosity, and your willingness to roll up your sleeves—so if you don't check every single box below, we'd still love to hear from you.

Responsibilities

• Lead federal government contracting. Legal subject matter expert for the commercial and compliance side of Amwell's federal government contracts—prime contracts, subcontracts, flow-down requirements, and program compliance obligations. This is the core of the role.
• Draft and negotiate commercial agreements. Independently handle time-sensitive contracts with U.S. and international customers, partners, vendors, and healthcare providers—including SaaS, software licensing, clinical services, professional services, business associate, reseller, and data protection agreements.
• Be a trusted advisor to the business. Help stakeholders think through contract structure, risk allocation, procurement requirements, healthcare regulatory considerations, privacy and data terms, and operational commitments—translating all of it into plain, actionable guidance.
• Support RFI/RFP responses. Provide legal and compliance review on customer proposals, including government procurement materials, certifications, contractual exceptions, and risk review.
• Help us stay compliant. Pitch in on regulatory and compliance work and special projects—especially where commercial, healthcare, privacy, and government program requirements intersect.
• Support employment matters. Work alongside HR and the Head of Legal on employment and separation agreements, workplace policies, and the everyday employment questions that come up at a growing company.
• Lend a hand on disputes and litigation. Help manage litigation holds, gather relevant information, coordinate with internal teams, outside parties, and outside counsel, support discovery and subpoenas, and weigh in on legal risk and settlement strategy.
• Collaborate across the company. Partner with cross-functional teams to land approvals on non-standard terms, take part in deal desk review, and make sure our commitments are accurately captured and realistic to deliver.
• Make us better as you go. Contribute to our contract templates, playbooks, processes, compliance controls, and self-service tools so the whole team works smarter over time.
• Get to know our world. Build a solid understanding of Amwell's healthcare technology platform, product roadmap, and provider services model so your advice is grounded in how the business actually works.

Requirements

• A J.D. from an ABA-accredited law school and active, good-standing membership in at least one U.S. state bar.
• Six to ten or more years of relevant legal experience, including meaningful commercial contracting work. In-house experience at a technology, healthcare, digital health, or SaaS company is a plus.
• Strong experience with federal, state, or local government contracting—procurement requirements, flow-down clauses, subcontracting, compliance obligations, public-sector RFPs, and regulated program support. This is central to the role, so it's a strong preference.
• Experience drafting and negotiating a range of agreements (technology, SaaS, software licensing, healthcare provider services, business associate, data protection, and professional services).
• Sound, practical judgment: the ability to spot what really matters, explain it clearly to non-lawyers, and offer a sensible path forward.
• Comfort with ambiguity—you can assess legal and operational risk, make a recommendation, and keep things moving without perfect information.
• Strong organizational instincts and attention to detail, with a knack for tracking complex contract, compliance, and stakeholder requirements.
• Clear, friendly written and verbal communication.
• A collaborative spirit—you genuinely enjoy working across teams and meeting people where they are.

Nice-to-haves

• A T1 public trust clearance (or eligibility for one).
• Familiarity with healthcare technology, digital health, telehealth, health plans, providers, privacy, or data security.

Benefits

• Flexible Personal Time Off (Vacation time)
• 401K match
• Competitive healthcare, dental and vision insurance plans
• Paid Parental Leave (Maternity and Paternity leave)
• Employee Stock Purchase Program
• Free access to Amwell’s Telehealth Services, SilverCloud and The Clinic by Cleveland Clinic’s second opinion program
• Free Subscription to the Calm App
• Tuition Assistance Program
• Pet Insurance