Director of Engineering

Director of Engineering

Caselle builds specialized, enterprise ERP software for local government agencies. We are seeking a Director of Engineering to lead our teams in a hands-on role that blends technical depth with people leadership.

You will drive technical excellence and foster a culture of ownership, passion, and innovation, where engineers take pride in building great software and solving real customer problems. Central to the role is transforming how teams design, build, test, and ship by pioneering spec-driven development and embedding AI across the development lifecycle. Working closely with Product, QA, and other department leaders, you will define strategy, influence roadmaps, and ensure the quality delivery of impactful solutions.

You will oversee a dual-platform environment, supporting legacy desktop applications while driving long-term modernization toward a scalable, web-based architecture.

Reports to: Chief Technology Officer Location: On-site / Hybrid

What You'll Do

People & Culture

• Lead, mentor, and grow engineers across cross-functional teams, providing technical guidance, coaching, and career development.
• Cultivate a culture of ownership, passion, innovation, and accountability, inspiring engineers to take pride in their craft and ship high-quality experiences.
• Lead engineering hiring, from recruiting strategy through onboarding.

Technical Leadership & AI

• Lead the integration of AI across the development lifecycle, from requirements through deployment, driving measurable gains in velocity, quality, and developer experience.
• Champion spec-driven development with Product and QA leadership, establishing clear specifications as the source of truth for engineers and AI-assisted tooling. Provide architectural and technical leadership, guiding design, reviewing code, and unblocking teams as needed.
• Oversee both legacy and modern platforms, keeping existing systems stable while driving migration to web-based technologies, and partner with DevOps on reliability, performance, and security.

Delivery & Operations

• Partner with Product Management to shape product strategy and roadmap decisions, and coordinate sprint and release planning with strong agile practices.
• Define and track engineering KPIs, and establish processes, standards, and best practices that scale.
• Own engineering metrics and report to the executive team on those metrics, project progress, risks, and tradeoffs.
• Lead incident response and escalations, including customer-facing discussions, ensuring post-incident reviews drive lasting improvements.

What You'll Bring

• 10+ years in software engineering, including 5+ years leading and scaling engineering teams.
• A track record of shipping reliable, scalable web-based systems; experience modernizing legacy platforms is a strong plus.
• Hands-on fluency with AI-assisted development tools and a clear point of view on transforming the SDLC with AI.
• Experience with spec-driven or specification-first development practices, partnering closely with Product and QA.
• Strong architectural judgment with enough hands-on depth to review code and unblock teams.
• Excellent communication with technical and non-technical stakeholders.
• Proven success recruiting, developing, and retaining engineering talent.

What Success Looks Like

• Teams consistently deliver high-quality software on predictable timelines.
• AI and spec-driven development are standard practice, measurably improving velocity, quality, and developer experience.
• The platform is reliable, secure, and steadily modernizing toward a scalable, web-based architecture.
• Engineering health is visible and improving, with the executive team confident in delivery, metrics, and progress.
• The team is strong and growing, with a culture of ownership, passion, and innovation that attracts and retains top talent