Senior AI Insights Analyst — Remote

Cypress HCM; United States; Remote; USD 120,000 - 180,000; Full time

Benefits offered by this job

401K 4% match

Wellness stipend

Medical insurance

Dental insurance

Long-term disability

Job summary

Cypress HCM is seeking a data/analytics professional to advance AI search capabilities for our SaaS Hospitality platform. You will lead evaluation frameworks, coordinate experiments, and refine prompts to improve content relevance and measurement across internal engines.

The role requires strong SQL/Python skills, Databricks familiarity, and startup experience. Remote within the United States with occasional travel, reports to the VP of Product.

Qualifications

• 5+ years of analytics, data science, research, or search product experience.
• 2+ years of experience with AI search, SEO/GEO/AEO, content performance, or LLM evaluation.
• Hands-on fluency with LLMs and agentic tooling for high-volume data collection and processing.
• Strong SQL and Python skills; Databricks experience preferred.
• Startup experience required; fast-moving, small teams with ownership.

Responsibilities

• Track how often, how favorably, and how accurately clients appear in AI answers versus a defined competitive set with baselines and uncertainty.
• Maintain the tracked-prompt panels across engines, topics, and markets and report movement over time.
• Identify which sources AI systems cite for a given topic and characterize that mix.
• Track whether and how published content surfaces as cited evidence and how long it lasts.
• Test which content traits make material more likely to be picked up by AI systems.
• Connect AI visibility to referral traffic, engagement, bookings/conversions and map measurability gaps.
• Evaluate AI answers for accuracy, relevance, and completeness; document failure modes over time.
• Refine how prompts are constructed and apply evaluation discipline to internal features.
• Stay ahead of how AI search retrieves/cites sources and ensure claims are re-derivable from inputs.

Skills

SQL

Python

LLM evaluation

AI search

Tools

Databricks

Job description

Cypress HCM is seeking a data/analytics professional to advance AI search capabilities for our SaaS Hospitality platform. You will lead evaluation frameworks, coordinate experiments, and refine prompts to improve content relevance and measurement across internal engines.

The role requires strong SQL/Python skills, Databricks familiarity, and startup experience. Remote within the United States with occasional travel, reports to the VP of Product.