VP of Engineering (AI)

Location: Remote within the United States

Total compensation: $250,000–300,000

Company

Venture-backed real estate technology company building online education and digital tools that make buying, selling, and managing real estate more efficient and transparent.

What you will do

• Lead the engineering organization and set standards for technical quality, ownership, and execution.
• Define technical direction across core systems, including decisions to extend, simplify, re-architect, or replace technology.
• Stay hands-on through architecture and code reviews, debugging, production issue resolution, and direct technical contribution.
• Improve the path from problem framing through implementation and production, simplifying scope and unblocking complex initiatives.
• Build engineering leadership through recruiting, coaching, organizational design, and performance management.
• Advance AI-assisted engineering by building platforms and guardrails that increase leverage across the company.

Requirements

• Significant software engineering experience, including leadership of engineering managers and senior technical leaders.
• Strong technical depth across architecture, implementation, debugging, and production systems.
• Experience evolving complex live systems and making sound decisions about extending, refactoring, or replacing them.
• Track record of improving engineering execution and developing high-performing teams.
• Strong product and business judgment with close partnership across Product and executive leadership.
• Deep hands-on experience with frontier AI development tools and a clear perspective on AI’s impact on software engineering.

Nice to have

• Experience scaling a startup through multiple stages of growth.
• Experience leading lean, high-autonomy engineering organizations.
• Experience modernizing legacy systems while supporting a live business.
• Experience with marketplaces, CRMs, workflow automation, communications platforms, or third-party APIs.
• Familiarity with AWS, JavaScript, Python/Django, PostgreSQL, or Ruby on Rails, or experience in real estate, fintech, marketplaces, or vertical SaaS.

Culture & Benefits

• Medical, dental, vision, and life insurance.
• 18 days of paid time off, increasing with tenure, plus 10 paid holidays.
• Annual professional development budget and paid tenure sabbaticals.
• Work-from-home stipend and access to Clever homeownership benefits.
• 401(k) retirement plan, 6–12 weeks of paid parental leave, and wellness benefits including counseling sessions.