Vice President, Engineering

About your role

The VP of Engineering – SMB will be responsible for leading the engineering group for Rocket Lawyer’s Solo & Micro Business (SMB) business team. This team builds and scales the products and services that enable entrepreneurs and business owners to form, manage, and grow their companies, while staying compliant and legally protected.

Reporting directly to the CTO, this leader will own the end-to-end engineering execution for the SMB business, working in close partnership with the Head of Business of SMB, product management, design, data, and AI teams. They will be responsible for driving delivery velocity, instilling engineering excellence, and scaling systems to meet customer and business needs.

This is a highly visible role where the leader will directly impact the company’s revenue and customer growth.

How you will make a difference day to day

• Leadership & Culture: Build and lead a high-performing SMB engineering team (currently ~40 people across US, BR & UK), fostering a culture of accountability, velocity, and innovation.
• Execution & Delivery: Ensure predictable and high-quality delivery of SMB product roadmap, while continuously improving engineering processes and outcomes.
• Cross-functional partnership: Work hand-in-hand with the SMB Business Head, product, design, Ops and AI teams to align business and technology priorities.
• Scalability: Architect and scale systems that support high-volume, customer-facing SMB products.
• People Development: Recruit, retain, and mentor top engineering talent; develop strong technical leaders within the SMB group.
• Data-driven Management: Use metrics and OKRs to measure engineering velocity, quality, and impact; drive continuous improvement.
• Modern Engineering Practices: Champion best practices including AI Development tools, CI/CD, cloud-native architectures, observability, and secure development lifecycles.
• AI Enablement: Collaborate with the AI team to embed intelligence into SMB experiences, leveraging Copilot and related initiatives.
• Mobile Ownership: Oversee Rocket Lawyer’s iOS and Android applications, ensuring they are fast, intuitive, and seamlessly integrated into the overall platform and Copilot.

What you’ll need

• 10+ years of progressive engineering leadership experience, including at least 5 years in VP/Director-level roles, with experience managing people managers and leading teams of 25+.
• Proven success leading geographically distributed teams (US/BR/EU) and working in matrix business structures
• Track record of building scalable, high-availability, secure cloud systems (GCP/AWS/Azure).
• Experience shipping customer-facing web products at scale, ideally in SaaS, e-commerce, or legal-tech/fintech.
• Experience with the latest front-end technologies and CMS systems.
• Deep familiarity with  high velocity, self-service Product Led Growth (PLG) motions - with proven ability to effectively collaborate with business leaders, product managers and design to deliver great customer experiences.
• Data-driven mindset; strong fluency with metrics, OKRs, and business outcomes.
• Excellent communication skills and executive presence; able to influence across C-suite.
• Deep technical knowledge of SEO/SEM.

Nice to Have

• Experience with SMB-focused products or compliance/formation services.
• Familiarity with legal-tech, fintech, or AI-enhanced workflows.
• Hands-on technical depth in Java or similar.
• Background scaling from startup → growth stage in a global, matrixed company.
• Familiarity with AEO/GEO (Answer Engine Optimization)
• Experience with Mobile web and app development.

Success in 12–18 Months

• SMB engineering velocity and predictability measurably improved.
• High-performing, stable SMB engineering leadership bench in place.
• Roadmap delivery tightly aligned with SMB business outcomes.
• Core SMB systems scaled for the next stage of Rocket Lawyer growth.
• SMB products seamlessly incorporate AI-powered capabilities in partnership with the Copilot team.

Not sure if you meet all the qualifications? Apply anyway! We value diverse experiences and encourage you to bring your unique talents to our team!

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
• 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