Senior Software Engineer - Strategic Initiatives (Office of the CTO)

Position Summary 

Bentley Systems is seeking a polyglot Senior Software Engineer to join a newly established, high-velocity Strategic Initiatives engineering squad operating directly within the Office of the CTO. Functioning as a small elite engineering team that operates as the CTO's incubator and technical accelerator that tackles Bentley's hardest technical challenges and blockers. This team is tasked with rapid prototyping, architectural de-risking, and accelerating tactical engineering initiatives across Bentley’s global product and technology landscape. 

The role sits at the intersection of engineering, architecture, and innovation, helping teams across Bentley resolve technical unknowns and move important initiatives forward. You'll have the autonomy to lead your own work, backed by the experience and collaboration of senior architects and engineers in the Office of the CTO. Your mission will be to build proof-of-concepts, experiment with emerging technologies like AI, and tackle complex challenges in distributed systems and cloud-native architecture. 

You will be instrumental in shaping the future of Bentley's products and platforms, working on everything from modernizing existing systems to creating entirely new solutions. This role offers a unique opportunity to work with a high degree of autonomy, collaborate with senior architects, and make a tangible impact on Bentley's strategic initiatives.  

Responsibilities 

• Architect, implement, and benchmark functional proof-of-concepts (PoCs) to accelerate and de-risk complex technical hurdles, validate performance, and evaluate emerging technologies before company-wide commitment. 

• Partner directly with executive technical leadership on exploratory engineering problems—translating open-ended concepts and ambiguous requirements into functional, testable software. 

• Move fluidly across technical domains depending on project needs, from deep performance profiling, memory optimization, and cloud reliability bottlenecks to microservices, APIs, and modern front-end spikes. 

• Take vague, high-level problem briefs and independently explore viable technical paths, establishing clarity and actionable solutions with minimal direction. 

• Package validated prototypes, architectural findings, and performance data into clean, maintainable deliverables so domain teams can seamlessly transition solutions into production. 

• Actively integrate modern AI-assisted engineering workflows (e.g., Claude, Copilot, Gemini, vector indexing/RAG architectures) into day-to-day development to shorten research cycles, accelerate code generation, and test hypotheses faster. 

Qualifications 

• 7+ years software engineering experience with a demonstrable track record of designing, building, and delivering complex, high-performance software in fast-paced, product-led environments. 

• Working fluency across multiple programming languages (such as C#, TypeScript, Python, Java, or C++), with the aptitude to pick the best tool for the specific problem at hand. 

• Solid foundational knowledge of distributed systems, multi-tenant patterns, containerized deployments (Docker, Kubernetes), and at least one major cloud platform (Azure, AWS, or GCP). 

• Hands-on experience investigating performance bottlenecks, concurrency issues, memory leaks, latency profiling, and network reliability. 

• Highly self-directed and comfortable operating autonomously without extensive supervision. 

• Practical experience leveraging generative AI APIs, vector retrieval/RAG patterns, or daily integration of AI-assisted engineering tools to amplify output. 

• Ability to synthesize complex technical discoveries, trade-offs, and architectural recommendations into direct, high-signal summaries for technical leadership. 

• Bachelor’s degree in Computer Science, Software Engineering, or equivalent practical experience.