Head of Commercial, Legal

*This is a hybrid role working from our Redwood City, CA Office

About Us

Observe.AI is the AI Agents platform for customer experience, designed to help organizations deliver faster, smarter, and more efficient customer service at scale. The platform enables businesses to deploy specialized AI Agents that autonomously execute work across the full CX lifecycle—from handling customer conversations to supporting frontline teams and optimizing operations.

Each AI Agent is purpose-built for a specific role, equipped to understand context, make decisions, take action, and continuously improve outcomes. This allows organizations to increase resolution speed, elevate service quality, and reduce operational costs while empowering your frontline team to focus on higher-value work.

Built on a CX-native foundation, Observe.AI helps leading brands like DoorDash, Affordable Care, Signify Health, and Verida improve customer satisfaction, boost agent productivity, and deliver consistent, scalable performance across every customer interaction.

Why Join Us

As Head of Commercial Legal, you will serve as Observe.AI’s senior in-house legal leader, overseeing all legal matters while working closely with our executive leadership and GTM teams.

You’ll manage and mentor one direct report, and take the lead on high-volume commercial contracting, complex partnerships, and compliance. 

This is a hands-on, high-impact role designed for a legal leader who thrives in fast-paced, growth-stage environments.

What You’ll Be Doing

• Lead the Commercial Legal Function: Own the full commercial legal strategy and operations for a scaling private SaaS business.
• Manage Commercial Contracts: Draft, negotiate, and close a high volume of SaaS agreements, including MSAs, DPAs, NDAs, and enterprise procurement contracts.
• Support Strategic Partnerships: Structure and negotiate channel partnerships, technology alliances, and co-selling agreements with global partners.
• Build Scalable Legal Infrastructure: Create contract templates, negotiation playbooks, and streamlined legal workflows to accelerate deal velocity.
• Ensure Risk & Compliance Readiness: Advise on key issues including data privacy (e.g., GDPR), IP, employment law, and cross-border transactions.
• Corporate & Governance Support: Partner with finance and leadership on equity matters, board governance, M&A activity, and investor-related legal needs.
• Team Leadership: Manage and develop one direct report (Legal Counsel or Contracts Manager), with future scope to grow the function.

What You’ll Bring To The Role

• Experience: 8–12 years of legal experience, with at least 5+ years in-house at a high-growth B2B SaaS preferred 
• Growth-Stage Background: Hands-on legal leadership through scaling phases—from ~$25M to $150M+ ARR—in a private company environment.
• Commercial & Strategic Expertise: Proven ability to manage complex, commercial contracts primarily for strategic and upper enterprise segment and high-impact partnership deals.
• SaaS Fluency: Deep understanding of SaaS contracting models, data protection laws (e.g., GDPR, CCPA), and IP considerations.
• Pragmatic Judgment: Business-first legal thinker with excellent negotiation, risk assessment, and problem-solving skills.
• Leadership: Experience managing people and operating as the sole or most senior legal authority in a fast-paced environment.
• Credentials: J.D. from an accredited law school and licensed to practice in California.

Why You’ll Love It Here  

• Competitive compensation including equity: Market-aligned base pay, performance incentives, and meaningful equity ownership
• Excellent medical, dental, and vision insurance options: Comprehensive medical, dental and vision benefits for employees and eligible dependents
• Flexible Paid Time Off: Our unlimited, flexible PTO policy empowers you to take the time you need to recharge, maintain balance, and perform at your best.
• Additional Time to Recharge: 10 company holidays, an annual company-wide Winter Break, and paid parental leave to fully support life outside of work.
• 401(k) plan: Long-term financial planning support with tax-advantaged retirement savings
• Quarterly Lifestyle Spending Account: Flexible quarterly stipend to support wellness, learning and professional development, and personal growth
• Monthly Mobile + Internet Stipend: Support for remote and hybrid work connectivity needs
• Pre-tax Commuter Benefits: Tax-efficient transit and commuting support for hybrid and in-office employees
• Autonomy and Agency: Play a meaningful role in scaling a category-defining GenAI platform transforming the future of customer experience.

Salary Range

The base salary compensation range targeted for this full-time position is $295,000 - $315,000 Range per annum. Compensation may vary outside of this range depending on a number of factors, including a candidate’s qualifications, skills, competencies and experience. Base pay is one part of the Total Package that is provided to compensate and recognize employees for their work, and this role may be eligible for additional discretionary bonuses/incentives and equity (in the form of options). This salary range is an estimate, and the actual salary may vary based on the Company’s compensation practices.

Our Commitment to Inclusion and Belonging

Observe.AI is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. Observe AI does not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws or prohibited by Company policy. Observe.AI also strives for a healthy and safe workplace and strictly prohibits harassment of any kind.

We welcome all people. We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals. We seek to hire, develop, and retain talented people from all backgrounds. Individuals from non-traditional backgrounds, historically marginalized or underrepresented groups are strongly encouraged to apply.

If you are ambitious, make an impact wherever you go, and you're ready to shape the future of Observe.AI, we encourage you to apply. For more information, visit www.observe.ai. 

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