Routeware, Inc.

Compensation

Full Description

POSITION OVERVIEW We are seeking a hands-on and strategic Director of Software Development to lead the development of key products in the Routeware portfolio. This role blends technical depth, organizational leadership, and execution excellence. You’ll lead multiple product engineering teams and technical architects responsible for delivering high-quality, scalable, and modern SaaS solutions. You will be instrumental in driving Routeware’s shift from siloed products toward a unified, API-first platform that supports growth, customer success, and innovation. This is a technology leadership role for a builder and modernizer — someone equally comfortable in design reviews, sprint demos, and strategic planning sessions. RESPONSIBILITIES Leadership & People Lead and mentor multiple product and platform development teams, architects, fostering a culture of ownership, technical excellence, and delivery discipline. Attract, retain, and develop top engineering talent across the US, Canada and CoE. Partner closely with Product and Architecture to deliver customer outcome based innovation. Technology & Delivery Oversee full-stack development for assigned products — from planning to deployment — ensuring predictable delivery, quality, and performance. Drive modernization of legacy systems toward a cloud-native, service-oriented, API-driven architecture aligned with the Technology Roadmap. Grow RouteWare Platform evolution — common services, APIs, identity, data, and observability layers that power all Routeware products. Strengthen CI/CD, test automation, and observability (DataDog, etc.) to move toward proactive issue detection and faster release cadence. Champion developer productivity initiatives — adoption of AI in SDLC, improving developer effectiveness, code quality, and cycle time, etc. through modern tools, metrics, and automation. Collaboration & Alignment Partner with Product Management on roadmap execution — translating business priorities into clear technical outcomes. Collaborate with the Architecture team on platform evolution, data unification, and modernization of the tech stack. Work cross-functionally with Customer Success and Operations to improve product reliability, upgradeability, and customer experience. Participate in R&D budgeting and capacity planning, ensuring alignment with company targets for efficiency and EBITDA. QUALIFICATIONS 10+ years of software engineering experience, with 5+ in engineering leadership roles. Proven success leading distributed teams delivering SaaS products at scale. Strong technical foundation in .NET, C#, SQL, REST APIs, and cloud-native (Azure/AWS) architectures. Demonstrated experience modernizing monolithic systems into modular, service-based architectures. Experience managing platform and application teams concurrently (APIs, shared services, core product). Hands-on familiarity with AI Development tooling, DevOps, CI/CD, infrastructure-as-code, and observability tools. Excellent communication skills — able to translate between business goals and technical strategy. Strong collaboration and influencing skills across Product, Architecture, and Operations. Why Routeware Join a company that combines mission-driven impact with cutting-edge technology. At Routeware, your work helps communities operate more efficiently and sustainably. You’ll be part of a leadership team transforming a traditional industry into a digital, data-driven future — powered by AI, modern engineering, and connected data platforms. BENEFITS Comprehensive benefits (medical with HSA option, vision, dental, and life insurance) Paid parental leave Medical and Dependent FSA 401K match Unlimited PTO Ten company holidays 1 Volunteer day Summer Friday's Routeware is an Equal Opportunity Employer and prohibits all forms of discrimination or harassment. At Routeware, we are committed to the principle of equality, and all employment decisions are based on job requirements, business needs, and individual qualifications, without regard to race, color, religion or belief, national, social or ethnic origin, sex (including pregnancy), age, physical, mental or sensory disability, HIV Status, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate.