VP of AI, Product and Engineering

About Rocket Lawyer

We believe everyone deserves access to affordable and simple legal services. Founded in 2008, Rocket Lawyer is the largest and most widely used online legal service platform in the world. With offices in North America, South America, and Europe, Rocket Lawyer has helped over 30 million people create over 50 million legal documents, and get their legal questions answered.

We are in a unique position to enhance and expand the Rocket Lawyer platform to a scale never seen before in the company’s history, to capture audiences worldwide. We are expanding our team to take on this challenge!

Role Overview

As VP of AI, Product and Engineering, you will help lead the evolution of Rocket Lawyer’s AI business. In close collaboration with the CTO, you will define the vision, strategy, and execution across product and technology, focused on building user-centric, scalable, and profitable AI solutions. Your leadership will help shape Rocket Copilot, the future of accessible, intelligent legal assistance, combining advanced artificial intelligence with our in-house legal expertise to simplify legal tasks for individuals and businesses.

We are seeking a product-minded AI executive who began their career as an engineer, holds advanced degrees in Computer Science or AI/ML (MS or PhD), and has demonstrated a strong ability to own both technical architecture and product lifecycle.

Key Responsibilities

• Define and drive the product and engineering roadmap for Rocket Copilot and the AI business unit.
• Lead cross-functional teams of AI/ML/Data/Software/QA engineers, product managers, and designers to deliver impactful AI-first experiences.
• Develop and execute Rocket Lawyer’s AI strategy, including LLM fine-tuning, RAG pipelines, prompt engineering, and in-house model development.
• Translate business goals into product features and AI use cases that deliver measurable user and revenue impact.
• Guide the evaluation, integration, or development of foundational models and infrastructure across GCP and open-source ecosystems.
• Build and lead a high-performing, diverse organization that blends deep technical excellence with strategic product thinking.
• Drive innovation in generative AI for legal workflows, document automation, and decision support.
• Maintain a deep understanding of user needs through research, data, and experimentation.
• Ensure AI systems meet standards of security, reliability, explainability, and regulatory compliance.
• Serve as a cross-functional partner to Legal, Product, GTM, and Executive teams to ensure AI efforts are integrated and aligned.

Required Experience & Qualifications

• 10+ years of experience in technology, with a strong foundation in AI/ML and product development.
• Proven experience launching and scaling LLM-driven products or platforms.
• Previous experience as a software engineer and demonstrated ability to engage in architectural and infrastructure decisions.
• Strong background in product leadership with clear examples of business impact.
• Advanced technical education: MS or PhD in Computer Science, Machine Learning, or a related field.
• Strong understanding of NLP, generative AI, RAG, prompt design, and AI evaluation methods.
• Strategic thinking and business acumen, including experience defining KPIs, pricing models, and product adoption strategies.
• Excellent communication and collaboration skills across technical and non-technical audiences.

Nice to Have

• Experience with AI model deployment in production environments (e.g., LangChain, Pinecone, OpenAI, Cohere, Anthropic, Mistral).
• Experience working in legal tech, B2B SaaS, or other regulated industries.
• Familiarity with privacy-preserving AI, enterprise compliance, and responsible AI governance.
• Contributions to research, patents, or open-source AI communities.

What We Offer

• A leadership role at the forefront of AI in legal tech.
• Opportunity to build and grow a new business unit within an established platform.
• Competitive compensation, including salary, equity, and performance-based incentives.
• Comprehensive health, wellness, and retirement benefits.
• A mission-driven, collaborative, and fast-paced environment.

Join us and help revolutionize how the world accesses legal help, powered by Rocket Copilot and led by you.

Benefits & Perks

• Comprehensive health plans (including Medical, Dental and Vision insurance for full-time employees)
• Unlimited PTO
• Competitive salary packages
• Life insurance
• Disability benefits
• Supplemental Optional Life Insurance Benefits
• FSA Options Optional
• HSA with Company Match
• 401k program with Company Match
• Fertility Assistance and Planning options
• Wellhub & ClassPass fitness platforms
• Comprehensive Pet Insurance options
• Financial Wellbeing & Student Loan Program access
• Access to additional Mental Health & Wellbeing resources
• Pre-tax Commuter/Transit Benefits
• Free Rocket Lawyer account with online access to an extensive legal documents library and brilliant licensed attorneys at discounted rates

Interview Process:

• Recruiter Phone Screen
• Role Assessment(s)
• Hiring Manager Interview
• Panel Interviews
• Final Interview

Rocket Lawyer is proudly committed to recruiting and retaining a diverse and inclusive workforce. As an Equal Opportunity Employer, we never discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, military or veteran status, status as an individual with a disability, or other applicable legally protected characteristics. We particularly welcome applications from veterans and military spouses.

All your information will be kept confidential according to EEO guidelines.

You may request reasonable accommodations by sending an email to hr@rocketlawyer.com_._

Compensation
Base salary range by location:

• San Francisco Bay Area, CA: $275,000 - $350,000
• Colorado: $255,000 - $294,000
• Utah, Arizona, and North Carolina: $240,000 - $277,200

Actual compensation packages are determined by various factors unique to each candidate, including but not limited to skill set, depth of experience, certifications, specific work location, and performance during the interview process.

$240,000 - $350,000 USD

By applying for this position, your data will be processed as per Rocket Lawyer Privacy Policy.