Senior Data Analyst

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

Location: Remote in the United States (ET/CT) | Travel: Occasional travel to NYC or Atlanta

Employees: 50 | Industry: SaaS, Hospitality, Media, Marketing | Reports To: Vice President, Product

Responsibilities

• Tracking how often, how favorably, and how accurately clients appear in AI answers versus a defined competitive set - with rigorous baselines, sampling, and stated uncertainty so real change can be distinguished from noise.
• Maintaining the tracked-prompt panels (across engines, topics, markets) this runs on, and report movement over time as the core output.
• Identifying which sources AI systems cite for a given topic and characterize that mix
• Tracking whether and how published content later surfaces as cited evidence, how long that takes, and how long it lasts - surfacing where a client's evidence base is thin and what's missing
• Testing which content traits (source, framing, format, specificity, recency, structure) make material more likely to get picked up by AI systems.
• Connecting AI visibility to real outcomes — referral traffic, engagement, bookings/conversions and build an honest instrumentation view of what's measurable today, what isn't, and where the recommendation-to-revenue chain breaks
• Evaluating AI answers for accuracy, relevance, and completeness; catalog failure modes by engine over time; maintaining the rubrics/benchmarks/rater-agreement process
• Continuously refining how prompts are constructed - applying the same evaluation discipline to any AI features built internally
• Staying ahead of how AI search systems retrieve/cite sources, validating claims via research (not industry commentary), defining product metrics with product/engineering, ensuring every customer-facing figure is fully re-derivable from documented inputs

Requirements

• 5+ years of experience in analytics, data science, research, and/or search products
• 2+ years of experience with AI search, SEO/GEO/AEO, content performance, or LLM evaluation
• Hands-on fluency with LLMs + agentic tooling – prompt design, evaluation harnesses, agents that collect and process data at volume
• Strong SQL and Python skills – experience with Databricks is preferred (or similar tools)
• Proven experience in experiment design applied to observational data – comparison group construction, difference-in-differences or matched comparison, and honest treatment of statistical power
• Strong analytical judgement with unstructured text: designing rubrics, coding qualitative signals into structured data, and reasoning carefully about ambiguous cases
• Startup experience is required – fast-moving, small teams, high visibility/ownership
• 401K with 4% match, monthly wellness stipend, comprehensive medical and dental insurance plans, long-term disability, and more