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.
Similar Jobs
.png){kind=logo}
_13.png)
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
