Senior Data Analyst

Why This Role Exists

Dearest is building the AI operating system for care navigation—a business-in-a-box platform for patient advocates that blends high-touch human support with tech-enabled workflows. As a Series A company, we are scaling fast. The next phase of growth requires operational precision, financial clarity, and decision-making powered by real-time intelligence. This role exists to build the analytics foundation that leadership, product, and operations will use to scale the company. You will not just build dashboards, you will define the metrics that run the business.

What You'll Own

• Build the Analytics & AI-Powered Data Engine

• Design and maintain company wide dashboards in Metabase and Amplitude.

• Define KPI frameworks across operations, growth, product, and finance.

• Design tracking architecture and guide engineering on instrumentation (Segment).

• Ensure a single source of truth across systems.

• Lay groundwork for predictive and AI-driven insights over time.

• Own the Data Layer

• Write advanced SQL

• Partner with product and engineering to refine schemas and data models.

• Improve data reliability, governance, and documentation.

• Contribute to scalable transformation workflows (dbt preferred).

• Drive Measurable Operational Leverage

• Identify workflow bottlenecks and quantify financial impact.

• Build models that inform hiring plans, capacity forecasting, and cost structure.

• Replace manual reporting with automated, scalable systems.

• Shift the organization from lagging indicators to leading indicators.

• Influence Strategic Decisions

• Translate complex analysis into clear business recommendations.

• Present findings directly to leadership.

• Support experimentation, forecasting, and growth modeling.

What You're A Fit For

• Core Technical Strength: Expert-level SQL

• Strong experience with cutting edge data tools (strong AI-first mindset)

• Deep familiarity with Metabase, PowerBI, Tableau

• Comfortable working with structured and semi-structured data (including JSON)

• Business & Startup Mindset: Think in systems, not spreadsheets. Care about business outcomes more than vanity metrics. Influence decisions, not just report numbers. Thrive in ambiguity and early-stage environments. High ownership, bias toward action.

Bonus Points

• If You’ve… Worked in healthcare or regulated environments.

• If You’ve… Built analytics infrastructure from scratch.

• If You’ve… Used dbt extensively.

• If You’ve… Used Python or R for automation or modeling.

A Bit About Dearest

We started Dearest after years of fighting the system for our own families—Arian's mom is beating pancreatic cancer today because he learned to hack insurance rules nobody explains. Our vision: everyone deserves a fighter like that. Today we mix smart software with human advocates to guide Medicare patients through diagnoses, bills, and care plans. Investors from Omada, Oscar, and UnitedHealthcare believe in the mission—and in the scrappy team of

• Human connection: We're bringing healthy human relating into the world as a healing modality, and we prioritize healthy relating within our team and in everything we do.

• Playful creativity: We bring levity, fun, and playfulness to our work.

• Excellence: in executing, thinking, writing, and communicating.

• Stop the ego: hard conversations and ripping the bandaid earlier than later.

• Uplift each other.

• Outwork smartly, competitive for our customers: Impact is driven that's measured on driving benefit to the end customer.

Our values: Conscious Leadership Values. Our story: Our Story.

Dearest is an Equal Opportunity Employer

We welcome applications from all qualified individuals, regardless of their background. Join us in transforming healthcare navigation.