VP of Engineering

About LeadSimple LeadSimple builds modern operations and communication software for residential property management companies. We serve thousands of customers and are expanding rapidly into enterprise workflows, automation, and AI-powered operations management. Role Overview LeadSimple is hiring a VP of Engineering to lead our engineering organization and drive the next chapter of our product evolution. This leader will partner closely with Product and Executive Leadership to build a world-class engineering culture, ship high-impact functionality, and meet the operational, security, and reliability standards expected by enterprise-grade customers. Responsibilities Leadership & Strategy Set the engineering vision and establish a high-accountability, high-autonomy operating model. Build, mentor, and scale a product engineering team across multiple disciplines (full-stack, platform, AI/ML, infrastructure). Partner with Product to shape roadmap priorities that balance customer value, architectural foundations, and long-term scalability. Strengthen domain expertise in property management operations and enterprise-grade workflow automation. Execution & Delivery Ensure predictable, high-velocity execution across multiple product squads. Own technical delivery for enterprise requirements including reliability, security, data integrity, and compliance. Improve engineering processes: code quality, testing strategy, CI/CD, incident response, metrics, and ongoing performance management. Drive cross-functional coordination across Product, Support, Success, and Sales. Architecture & Technology Oversee architectural direction for LeadSimple’s platform (Rails, React, Next.js, AI systems, telephony infrastructure). Own the scalability strategy for workflow automation, communication infrastructure, and trust-accounting systems. Lead build-vs-buy decisions, evaluate new technologies, and ensure the platform is positioned for durable innovation. Strengthen reliability across messaging, telephony, and integration surfaces. Requirements 7–10+ years of engineering leadership experience in SaaS, including managing managers. Demonstrated success scaling an engineering team through growth stages ($5M–$30M+ ARR preferred). Strong technical foundation in modern application architecture, distributed systems, and cloud infrastructure. Prior ownership of enterprise-grade delivery standards (security, uptime SLAs, integrations, data architecture). Ability to balance rapid iteration with long-term platform stewardship. Clear, proactive communicator who can partner closely with Product and advise executive leadership. Nice to Have Experience in workflow automation, communications (VoIP/SMS), or fintech-style ledger systems. Background in property management, real estate tech, or vertical SaaS. Experience building AI-augmented product functionality. Why LeadSimple Opportunity to drive the technical strategy of a profitable, growing vertical SaaS company with an ambitious product roadmap. Work directly with the CEO and senior leadership team on high-impact initiatives. A remote-first culture with strong autonomy, ownership, and performance standards. Competitive compensation, equity opportunities, and leadership influence.