Principal Architect - Empower the Future of Travel with Blockskye

Blockskye is seeking a thoughtful, AI-forward Software Architect to design and guide the development of scalable, high-performance, AI-native systems that power our next-generation travel and expense infrastructure. In this role, you'll work closely with engineering leads and product stakeholders to define architecture - including LLM integration, retrieval-augmented generation (RAG), and agent orchestration - improve system reliability, and ensure technical consistency across projects.

You'll play a critical role in shaping both the structure of our platform and the standards by which we build it, balancing long-term technical vision with pragmatic delivery. The ideal candidate has a strong background in modern web architectures on AWS and polyglot fluency across backend languages, hands-on fluency in modern AI engineering (LLMs, RAG, agents, evals), demonstrates deep systems thinking, and is comfortable operating across multiple teams.

We value engineers who prioritize clarity, maintainability, and simplicity - and who enjoy mentoring others while leading by example. Excellent fluency in oral and written English is essential for collaborating across our remote-first team.

Responsibilities:

• Hands-on coding solving complex problems.
• Design and evolve the overall software architecture for Blockskye's core platform, ensuring scalability, maintainability, and performance across services.
• Define and evolve the architecture for Blockskye's AI systems - model selection, prompt orchestration, retrieval-augmented generation (RAG), tool/function calling, agent patterns, evals, guardrails, observability, and cost/latency management.
• Architect for responsible AI: data governance for LLM workflows, PII handling, prompt-injection and hallucination defenses, and auditable decision trails for AI-assisted travel, payments, and expense transactions.
• Lead the team's adoption of AI-augmented engineering - setting standards for AI coding assistants (Claude Code, Cursor, GitHub Copilot) and agentic development workflows, and embedding them into architectural reviews and delivery.
• Collaborate with engineering leadership and product stakeholders to translate business goals into robust technical solutions.
• Define and enforce coding standards, architectural patterns, and system design best practices across engineering teams.
• Provide hands-on guidance and mentorship to developers during system design, implementation, and code reviews
• Lead architectural decision-making for major new initiatives, integrations, and platform enhancements.
• Evaluate and select tools, frameworks, and third-party solutions aligned with business and technical requirements.
• Partner with DevOps and Infrastructure teams to ensure highly available, secure, and observable cloud-native systems (primarily in AWS).
• Create and maintain technical documentation for architecture diagrams, workflows, and system dependencies.
• Contribute to system reliability and performance by identifying and resolving bottlenecks, inefficiencies, or architectural debt.
• Participate in early-stage technical scoping and estimation for roadmap initiatives.
• Drive the adoption of modern development practices such as microservices, event-driven architecture, and CI/CD.
• Review and guide API design (REST, Webhooks, etc.) to ensure clean, consistent, and versioned interfaces across teams and external partners.
• Help facilitate cross-team architectural alignment and knowledge sharing through regular design reviews and technical discussions.
• Support compliance, security, and data governance requirements from an architectural perspective (e.g., data flow diagrams, access controls).
• Stay current with emerging technologies, tools, and architectural patterns to inform long-term platform evolution.
• Serve as a key thought partner in Blockskye's transition from a startup architecture to an enterprise-grade platform.

Requirements

• Bachelor's degree in Computer Science, Software Engineering, or a related field; advanced degree preferred
• 8+ years of progressive experience in software development, including at least 2-3 years in an architecture or senior technical leadership role
• Polyglot fluency across backend languages and modern web frameworks (e.g., Node.js, Python, PHP/Laravel, Go), with the ability to become productive quickly in unfamiliar stacks
• Hands-on experience architecting production LLM-powered systems against at least one frontier model provider (e.g., Anthropic Claude, OpenAI), with solid command of prompt engineering, structured output, tool/function calling, retrieval-augmented generation (RAG), and agent orchestration.
• Daily, fluent use of AI coding assistants (Claude Code, Cursor, GitHub Copilot, or equivalent), with a demonstrated ability to define and teach standards for their safe, effective use across a team - including agentic workflows for real engineering work, not just autocomplete.
• Working knowledge of AI system evaluation (offline evals, A/B testing of prompts and models), guardrails for hallucinations, prompt injection, and PII, cost and latency management, and AI observability in production.
• Strong understanding of software architecture patterns, including microservices, event-driven systems, and domain-driven design
• Demonstrated experience designing scalable, cloud-native systems, particularly on AWS (e.g., Lambda, RDS, S3, ECS/Fargate)
• Proficiency in designing and maintaining secure, maintainable, and well-documented RESTful APIs and system interfaces
• Strong working knowledge of databases, including MySQL and caching strategies (e.g., Redis), with experience in query optimization and data modeling
• Experience with CI/CD pipelines, infrastructure-as-code, and observability tools (e.g., CloudWatch, Datadog, Sentry)
• Ability to translate business requirements into high-level system designs and detailed technical specifications
• Proven ability to mentor engineers, lead cross-functional technical discussions, and drive consensus
• Excellent communication and interpersonal skills, with fluency in written and spoken English for remote collaboration
• Comfort operating in a remote-first, startup-to-scaleup environment with evolving systems and priorities
• A collaborative mindset and a strong sense of ownership, quality, and continuous improvement

Preferred Qualifications:

• HR certification (SHRM-CP, PHR) is a plus.
• Experience with blockchain technologies, smart contracts, or distributed ledger integrations
• Background in travel, fintech, or enterprise SaaS platforms
• Experience modernizing legacy systems or leading platform migrations
• Familiarity with WebSockets, GraphQL, or message queue systems (e.g., SQS, Kafka)
• Experience fine-tuning, distilling, or post-training models, or building custom eval suites at scale.
• Contributions to open-source AI tooling or to the Model Context Protocol (MCP) / agent ecosystem.

Please note, this job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required. Duties, responsibilities and activities may change or new ones may be assigned at any time with or without notice.