Principal Software Engineer, AI Systems

Vacatia•Portland, OR

1d•Hybrid

About The Position

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.

Requirements

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 with REST APIs, webhooks, event-driven architectures, queues, retry patterns, and idempotent systems
Strong familiarity with modern AI model ecosystems, including frontier and open-weight models
Experience designing evaluation frameworks, observability systems, and operational measurement practices for AI workflows
Proven technical leadership experience through architecture ownership, mentorship, and long-term systems design
Strong software engineering fundamentals including testing, deployment hygiene, reliability, and operational ownership

Nice To Haves

Production experience with multiple agent frameworks and orchestration approaches
Experience evaluating and implementing AI observability and evaluation tooling
Experience working with messy operational datasets including transcripts, support interactions, and semi-structured logs
Experience serving as the senior-most IC on a growing engineering team
Familiarity with Salesforce AI products and Service Cloud Voice
Experience with AWS Connect or contact center technologies
Background supporting customer experience or operations organizations
Open-source contributions, conference speaking, or technical writing in the AI space

Responsibilities

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