Contract Review Attorney

About Headshots.com

At Headshots.com, we're reimagining how professional headshots are created and delivered. Trusted by clients like Boeing, Capital One, and American Express, we transform smartphone selfies into polished, studio-quality portraits within three business days. As our enterprise client base expands across industries and geographies, including a growing footprint in regulated healthcare environments, we are building out our legal function to support that growth.

We're looking for a Contract Review Attorney, reporting to the Chief Operating Officer, who will own the day-to-day review and negotiation of commercial agreements, partner closely with our business teams, and help us scale a thoughtful, risk-calibrated approach to enterprise contracting.

About the Role

This role combines hands-on contract review with a strategic understanding of how commercial terms translate into operational risk and opportunity. You will be the primary reviewer on incoming Master Services Agreements, Business Associate Agreements, Data Processing Addenda, Statements of Work, and vendor contracts. You will work directly with leadership to redline, negotiate, and finalize agreements that protect the company while preserving the speed and flexibility that allow us to serve enterprise clients well.

We are looking for someone who brings both technical legal expertise and strong commercial judgment, someone who can identify which provisions matter, where to push, and where to accept reasonable client positions in service of getting deals closed.

Key Responsibilities

• Lead the review and redlining of MSAs, BAAs, DPAs, SOWs, NDAs, and vendor agreements. Identify risk, draft fallback positions, and negotiate directly with client legal teams when needed. Translate complex legal terms into clear, plain-language recommendations for the business.
• Coordinate with the business on Standard Contractual Clauses, data transfer impact assessments, and DPA terms.
• Negotiate indemnification, limitation of liability, insurance requirements, IP ownership, audit rights, termination, and assignment provisions in a way that is proportionate to our scope and revenue.
• Develop playbooks and fallback positions so the business can move quickly on standard issues. Maintain contract templates, position playbooks, and a clause library.
• Work directly with sales, operations, and leadership to support active deal cycles. Translate legal positions into commercial recommendations. Provide guidance during pre-contract discussions so issues are surfaced early.
• Track the status of in-flight negotiations and ensure timely follow-up with client counterparties.

What You Bring

Experience & Qualifications

• Law degree (JD or LLM) from an accredited institution
• Six or more years of commercial contracts experience, with meaningful time spent in-house or supporting in-house teams.
• 5+ years of demonstrated experience reviewing and negotiating agreements (US and European commercial clients a plus)
• Working knowledge of GDPR and cross-border data transfer requirements.
• Strong command of commercial provisions: indemnification, limitation of liability, IP ownership, insurance, confidentiality, data security, termination, and assignment.
• Familiarity with SaaS, professional services, and vendor agreements.
• Excellent English skills, both written and spoken.

Mindset & Strengths

• Commercial pragmatism. You understand that legal review serves business outcomes, and you know when to push, when to compromise, and when to escalate.
• Clear written communication. You can explain complex legal positions to non-lawyers in plain language and translate client redlines into clear recommendations.
• Calm and thorough under deadline pressure. You can manage multiple active negotiations without losing track of detail.
• Independent operator. You can run a contract review process end-to-end with limited supervision and know when to surface issues to leadership.
• Discretion and trustworthiness. You handle confidential business information with care.
• A no-ego collaborator. You build trust through transparent communication, take ownership of your work, and welcome feedback.

Why Join Us

Fully remote, flexible schedule with ET overlap. Work directly with founders and executive leadership on agreements that shape the company's growth. Opportunity to build out the legal function and contracting infrastructure at a fast-moving company. Exposure to a diverse, enterprise client base across industries and geographies.

IMPORTANT

Direct inquiries will disqualify candidates.

Compensation: $40-60/hour depending on experience