VP of Architecture and Engineering

Vice President of Architecture and Engineering

Reports to: Chief Technology Officer | Location: Northeast Ohio (Hybrid)

Foundation Software LLC

Since 1985, Foundation Software has been a leading provider of software and services built specifically for the construction industry. Our integrated solutions support contractors throughout the entire project lifecycle, from estimating and job cost accounting to project management, HR, time tracking, and payroll processing.

With more than 600 team members and offices across the United States, we combine industry expertise, technology, and exceptional service to help our customers work more efficiently and successfully. At Foundation Software, employees have the opportunity to contribute to meaningful solutions while learning and growing as part of a collaborative team.

About the Role

Our construction accounting platform brings together the core financial and operational capabilities contractors depend on: job costing, payroll, invoicing, vendor payments, integrations, and financial reporting. Because these capabilities are business-critical, reliability, security, accuracy, and thoughtful technology evolution are essential.

Reporting to the CTO, you'll lead our architecture and software engineering organization and serve as a key strategic and technical partner. This executive role requires both strong organizational leadership and significant technical depth. You'll set engineering direction, build high-performing teams, mature our engineering practices, and drive the modernization of a complex, mission-critical platform.

What You'll Do

Engineering and Organizational Leadership

• Lead the full software development lifecycle, including architecture, development, integrations, APIs, and solution delivery, through Directors, Managers, architects, and senior technical leaders.
• Set and execute the architecture and engineering strategy, aligning capacity to business priorities.
• Own organizational design, performance management, talent strategy, and succession planning, and develop the next generation of engineering and architecture leaders.
• Build a culture of accountability, technical excellence, and continuous improvement, where decisions are made at the right level within clear guardrails.

Architecture and Technical Leadership

• Serve as the CTO's key advisor on significant architecture and technology decisions.
• Build and mature the Enterprise Architecture practice, including architecture principles, reference architectures, ADRs, architecture reviews, technology standards, and lifecycle management.
• Establish governance that improves consistency and decision quality without creating barriers to delivery.
• Maintain the technical depth to challenge assumptions, evaluate tradeoffs, and engage credibly with architects and senior engineers.

Platform Modernization

• Own the incremental modernization of a complex legacy applications toward SPA, microservices, and API-oriented architecture.
• Build an executable technical roadmap that balances modernization, technical debt, reliability, security and product priorities.
• Ensure technology investments deliver clear business value rather than following trends, while keeping the existing platform stable.

Engineering Effectiveness and SDLC

• Own and continuously improve the SDLC to increase delivery speed, quality, predictability, and productivity.
• Define a meaningful engineering KPI strategy covering delivery performance, technical health, reliability, and developer experience, and avoid simplistic individual productivity metrics.
• Operationalize approved AI capabilities within engineering workflows in line with company AI strategy and governance.

Security and Reliability

• Own security architecture and secure engineering practices, working closely with the Security organization on policy, risk, and compliance.
• Ensure architecture decisions account for the operational risks of payroll, accounting, payments, and financial reporting.
• Partner with QA and DevOps to improve release quality and operational resilience.

Cross-Functional Partnership

• Serve as the senior engineering partner to Product. Product owns priorities, roadmap, and timing, while Engineering owns how solutions are designed and built.
• Translate business objectives into scalable technical approaches, and partner with QA, PMO, DevOps, and Security on quality, predictability, and risk.
• Base decisions on evidence, business outcomes, and long-term platform health.

Financial and Vendor Management

• Own the engineering budget, capacity planning, and resource allocation across new development, maintenance, modernization, and technical debt.
• Shape resource strategy with the CTO, including the mix of employees, contractors, offshore/nearshore resources, and external partners.
• Manage strategic vendors and negotiate Statements of Work, with clear performance measures and accountability.

What Success Looks Like

• A clear, actionable architecture and engineering strategy aligned with business and product priorities
• High-performing teams with clear ownership and strong technical leadership
• Measurable progress on modernization, technical debt reduction, and high-value product delivery
• Improved reliability, scalability, security, and operational excellence
• A strong bench of future engineering and architecture leaders

What You Bring

• 15+ years of progressive experience in software engineering or architecture, including 5+ years in senior or executive leadership
• Demonstrated success leading and developing Directors, Managers, architects, and senior technical professionals across multiple engineering functions
• A proven record leading modernization of large, complex legacy platforms
• Deep expertise in SaaS and cloud architecture, distributed systems, APIs, and modern application design, with significant Microsoft Azure experience
• Experience establishing architecture governance, technical standards, and engineering practices
• Experience leading distributed organizations and managing offshore/nearshore partners, budgets, vendors, and SOWs
• A strong understanding of modern SDLC, secure software development, and engineering effectiveness
• Experience leading multi-product engineering organizations through growth and organizational change
• Strong executive communication skills and the ability to influence technology, product, and business leaders

Preferred Qualifications

• Experience with ERP, accounting, payroll, payments, fintech, construction technology, or other transaction-intensive applications
• Experience modernizing monolithic applications toward SPA, microservices, and API architectures
• Experience with Enterprise Architecture practices and technology lifecycle management
• Experience leading engineering metrics, developer experience, or effectiveness programs
• Experience applying AI-assisted development in enterprise engineering organizations

The Ideal Candidate

You're strategic and practical, with the technical credibility and judgment to balance long-term architecture against near-term business needs. You're a collaborative, low-ego leader who listens well, empowers others, and holds people accountable, and you use technology to solve real problems rather than for its own sake.