Senior Software Engineer, Data & AI

Overview Holly is the HR platform built for city and county government. We help local governments modernize how they hire, classify, and manage their workforce — work that directly shapes public services for millions of people. Our platform is live across 12 states with 60+ jurisdictions representing over 10% of the US population, including major counties like Santa Clara and Contra Costa in the Bay Area, Orange County in LA, and Snohomish County in Washington State. Demand is outpacing our team, and we’re building to meet it.

Holly is a seed-stage team of 20+ operators with deep roots in public service, civic tech, and AI. We’ve raised $10M from leading investors in government technology and the future of work and have grown over 100X in the last year. We center public servants and impact in every decision, and we bring that same care to how we work here at Holly.

About The Role We’re hiring a Senior Software Engineer, Data & AI to build Holly’s Data Platform. Local governments publish enormous amounts of public information salary schedules, job classifications, MOUs (Labor Union Agreements), budgets but it’s scattered across thousands of websites and buried in messy formats: scanned PDFs, inconsistent HTML, spreadsheets, and everything in between. Turning that chaos into clean, searchable, trustworthy data is one of our biggest product challenges and deepest moats.

You’ll design and build the Data Platform ingestion and processing pipelines, canonical datasets, semantic search and retrieval, and inference APIs that product engineers can build on. AI is part of the infrastructure, not a layer added later. You’ll use models where they improve extraction, classification, normalization, matching, and search, then evaluate and operate those systems in production.

This is a hands-on, high-ownership engineering role. You’ll own major data systems, make architecture calls, and raise the standards for how Holly collects, models, and trusts its data. You’ll work directly with the founders and partner closely with product engineers to make sure they have clean, reliable data to build on.

If you’ve worked with large, high-volume data and love the challenge of taming messy real-world inputs into something people can rely on, we’d love to talk.

What You’ll Do You’ll own major parts of the Data Platform end to end, make high-leverage technical decisions, and build the data and AI infrastructure the rest of the product depends on.

Own and Build the Data Platform

• Own the data platform end-to-end from raw public sources to clean, canonical datasets the product consumes
• Design the architecture, schemas, and standards for how Holly ingests, models, and trusts its data
• Partner with the founders to scope work, make tradeoffs, and drive delivery on our highest-leverage data initiatives
• Help set the long-term direction for our data foundation

Build Ingestion & Normalization Pipelines

• Build systems that collect large volumes of public government data from thousands of local-government sources across the web
• Turn messy, heterogeneous inputs scanned PDFs, inconsistent HTML, spreadsheets into structured, normalized data (parsing, extraction, OCR, dedupe, entity resolution, schema mapping)
• Where it adds leverage, incorporate LLM-assisted extraction and embeddings into the pipeline
• Build for freshness, reliability, and scale so data stays current and trustworthy

Model & Serve Data for the Product

• Design canonical data models and domain schemas that product engineers build on
• Expose clean, versioned, well-documented datasets the main app can reliably consume
• Own data quality, validation, lineage, and observability so downstream teams can trust what they’re building on

Build Search & AI Infrastructure

• Build semantic search and retrieval over large, changing government datasets
• Design inference APIs for extraction, classification, matching, and other AI-powered data processing
• Build evals, tracing, and fallbacks so model behavior is measurable and dependable
• Give product engineers clear interfaces for using data and AI capabilities

Make It Automated & Intelligent

• Evolve pipelines from manual/one-off toward automated, self-healing, monitored systems
• Establish data-quality checks, alerting, and standards that keep the platform reliable as it grows
• Raise the bar on how we collect, validate, and serve data across the comp…