Principal Software Engineer, AI Systems

Job Description : Founding AI EngineerLocation: Portland, OR (Hybrid – three days in office); Remote considered for exceptional candidatesCompany: Vacatia – Building the future of AI-powered hospitalityRole OverviewWe are launching a brand-new AI engineering function focused on building the foundational operating layer for every AI initiative at Vacatia. This is true zero-to-one platform building work. No existing AI stack. No inherited patterns. No predetermined tooling. You’ll help define all of it.Why You’ll Love Working at VacatiaBuild foundational AI infrastructure from the ground up with significant architectural ownershipShape the long-term AI strategy for an entire businessWork on meaningful operational and customer-impact problems – not experimental side projectsOperate with executive-level visibility and support for AI investmentInfluence the engineering culture, standards, and technical direction of a growing teamJoin early enough to meaningfully define the platform, practices, and roadmapReceive equity participation through stock options as part of total compensationYour ImpactAs the founding engineer for this initiative and the senior-most individual contributor on the team, you’ll architect and operationalize the systems that power every AI workflow at Vacatia.You’ll OwnAI Platform Strategy & Architecture: Define technical strategy and foundational stack; evaluate runtimes, orchestration patterns, agent frameworks, model providers, and observability tooling; lead build-vs-buy decisions.Agent Infrastructure & Deployment: Design runtime, orchestration, deployment, and CI/CD patterns; establish prompt, tool, and workflow versioning strategies; build scalable deployment pipelines.Evaluation, QA & Reliability: Build evaluation harnesses, regression testing systems, replay tooling, and operational QA frameworks; define measurable standards for agent performance.Analytics & Observability: Implement tracing, structured logging, telemetry, and dashboarding; develop operational visibility into agent behavior and failure modes.Systems Integrations & Data Infrastructure: Build production integrations across Salesforce, AWS Connect, internal platforms, and support systems; create data transformation and ingestion pipelines.Technical Leadership & Team Growth: Establish engineering standards, architecture patterns, and operational discipline; mentor future engineers; contribute to hiring and onboarding.What You BringRequired Experience10+ years of backend or full-stack engineering experience building and operating production systems at scaleDeep, hands-on experience designing and deploying LLM-powered or agentic systems in production environmentsStrong architectural judgment across AI systems, backend infrastructure, and distributed integrationsExpertise with REST APIs, webhooks, event-driven architectures, queues, retry patterns, and idempotent systemsStrong familiarity with modern AI model ecosystems, including frontier and open-weight modelsExperience designing evaluation frameworks, observability systems, and operational measurement practices for AI workflowsProven technical leadership experience through architecture ownership, mentorship, and long-term systems designStrong software engineering fundamentals including testing, deployment hygiene, reliability, and operational ownershipStrongly PreferredProduction experience with multiple agent frameworks and orchestration approachesExperience evaluating and implementing AI observability and evaluation toolingExperience working with messy operational datasets including transcripts, support interactions, and semi-structured logsExperience serving as the senior-most IC on a growing engineering teamNice to HaveFamiliarity with Salesforce AI products and Service Cloud VoiceExperience with AWS Connect or contact center technologiesBackground supporting customer experience or operations organizationsOpen-source contributions, conference speaking, or technical writing in the AI spaceJoin UsThis is an opportunity to define the AI foundation for an entire company at the moment the investment and urgency are real. If you enjoy solving operationally messy, technically complex problems – and want ownership over the systems, patterns, and standards that shape what comes next – we’d love to hear from you.