Principal Software Engineer, AI Systems

Join Vacatia and Build the Future of AI-Powered Hospitality

Location:

Portland, OR (Hybrid — three days in office)

Remote considered for exceptional candidates

Vacatia 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.

• Build foundational AI infrastructure from the ground up with significant architectural ownership
• Shape the long-term AI strategy for an entire business
• Work on meaningful operational and customer-impact problems — not experimental side projects
• Operate with executive-level visibility and support for AI investment
• Influence the engineering culture, standards, and technical direction of a growing team
• Join early enough to meaningfully define the platform, practices, and roadmap
• Receive equity participation through stock options as part of total compensation

As 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.

• Define the technical strategy and foundational stack for AI systems at Vacatia
• Evaluate and select runtimes, orchestration patterns, agent frameworks, model providers, and observability tooling
• Lead critical build‑vs‑buy and vendor evaluation decisions

• Design the runtime, orchestration, deployment, and CI/CD patterns for AI agents
• Establish prompt, tool, and workflow versioning strategies
• Build scalable deployment pipelines that support safe iteration and production reliability

• Build evaluation harnesses, regression testing systems, replay tooling, and operational QA frameworks
• Define measurable standards for agent performance and production reliability
• Create systems that enable rapid experimentation without sacrificing quality

• Implement tracing, structured logging, telemetry, and dashboarding across AI workflows
• Develop operational visibility into agent behavior, performance, and failure modes
• Ensure outcomes are measurable and tied to business impact

• Build production integrations across Salesforce, AWS Connect, internal platforms, and customer support systems
• Create data transformation and ingestion pipelines for transcripts, recordings, operational data, and documents
• Develop the infrastructure that allows AI systems to interact effectively with real business operations

• Establish engineering standards, architecture patterns, and operational discipline
• Mentor future engineers joining the team
• Contribute to hiring, onboarding, and technical growth as the organization scales
• You’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.

• 10+ years of backend or full-stack engineering experience building and operating production systems at scale
• Deep, hands-on experience designing and deploying LLM-powered or agentic systems in production environments
• Strong architectural judgment across AI systems, backend infrastructure, and distributed integrations
• Expertise…