[Hiring] VP of Engineering @LeadSimple

Role Description

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.

Qualifications

• 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.

Benefits

• 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.