VP of Engineering - LeadSimple

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 p