Vice President of Architecture and EngineeringReports to: Chief Technology Officer | Location: Northeast Ohio (Hybrid)
About the RoleOur 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 CandidateYou'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.
