Principal Software Engineer, AI Systems

Join Vacatia and Build the Future of AI-Powered HospitalityLocation: Portland, OR (Hybrid — three days in office)Remote considered for exceptional candidatesVacatia is building the future of timeshare and vacation ownership. We operate in a fragmented, operationally complex industry, and we believe AI is the lever that allows a small, high-performing team to fundamentally reshape how the business operates.The problems here are real and consequential — owner mortgage outcomes, rental revenue optimization, contact center intelligence, and operational decision-making across dozens of resorts — all powered by data that has historically been underutilized and poorly connected.We’re launching a brand-new AI engineering function focused on building the foundational operating layer for every AI initiative at Vacatia: agent infrastructure, evaluation and observability systems, integrations across customer-facing platforms, and the data pipelines that make intelligent workflows possible.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 & ArchitectureDefine the technical strategy and foundational stack for AI systems at VacatiaEvaluate and select runtimes, orchestration patterns, agent frameworks, model providers, and observability toolingLead critical build-vs-buy and vendor evaluation decisionsAgent Infrastructure & DeploymentDesign the runtime, orchestration, deployment, and CI/CD patterns for AI agentsEstablish prompt, tool, and workflow versioning strategiesBuild scalable deployment pipelines that support safe iteration and production reliabilityEvaluation, QA & ReliabilityBuild evaluation harnesses, regression testing systems, replay tooling, and operational QA frameworksDefine measurable standards for agent performance and production reliabilityCreate systems that enable rapid experimentation without sacrificing qualityAnalytics & ObservabilityImplement tracing, structured logging, telemetry, and dashboarding across AI workflowsDevelop operational visibility into agent behavior, performance, and failure modesEnsure outcomes are measurable and tied to business impactSystems Integrations & Data InfrastructureBuild production integrations across Salesforce, AWS Connect, internal platforms, and customer support systemsCreate data transformation and ingestion pipelines for transcripts, recordings, operational data, and documentsDevelop the infrastructure that allows AI systems to interact effectively with real business operationsTechnical Leadership & Team GrowthEstablish engineering standards, architecture patterns, and operational disciplineMentor future engineers joining the teamContribute to hiring, onboarding, and technical growth as the organization scalesYou’ll partner closely with Product, Engineering Leadership, and Vacatia’s broader AI transformation initiatives to define how AI systems are built and operationalized across the company.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.