Senior Data Analyst

Build the intelligence engine powering the future of care navigation.

📍 Location + Work: United States (Remote) — must be U.S.-based
💼 Type: Full-time — Early team, high ownership
🛠 Data Stack: Advanced SQL, Metabase, Amplitude, Segment, dbt (preferred), Python (optional)

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.

• 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.

• 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).

• 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.

• Translate complex analysis into clear business recommendations.

• Present findings directly to leadership.

• Support experimentation, forecasting, and growth modeling.

• Leadership runs the company on dashboards you built.

• Manual reporting is nearly eliminated.

• Operational efficiency and margin improve measurably.

• Forecasting accuracy increases across growth and ops.

• Data trust is high across all teams.

• Expert-level SQL

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

• Deep familiarity with Metabase, PowerBI, Tableau

• Experience managing tracking with Segment
  Comfortable working with structured and semi-structured data (including JSON).

• 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.

• Worked in healthcare or regulated environments.

• Built analytics infrastructure from scratch.

• Used dbt extensively.

• Used Python or R for automation or modeling.

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 <10 building it.

Founded by experienced entrepreneurs with successful exits and deep healthcare + tech expertise. Backed by top-tier investors and advisors, including founders and executives from Oscar Health, Omada, Galileo, One Medical, Ro, United, Uber, and Postmates.

We move fast and execute with purpose, operating with a lean, impact-driven mindset. We're guided by principles of conscious leadership, a commitment to getting things done (GSD), and a focus on achieving results through hard work, rapid iteration, and swift execution.

Dearest is a fast-moving, high-impact startup where chaos is the norm, and ownership is key. There's no playbook—some days, you'll put out fires; other days, you'll build from scratch. If you thrive in ambiguity, take initiative, and solve problems without waiting for direction, you'll fit right in. If you need structure and predictability or 'need to be a manager' this isn't for you. The upside? You'll level up and have growth, work with an elite, A+ team, and make a real impact as we scale. This isn't a corporate place, be advised.

We envision a future where every American has access to a personal healthcare navigator. Our platform is designed to democratize healthcare navigation, offering tools and resources that were previously unavailable to many. By addressing the challenges faced by patient advocates and those navigating chronic diseases or healthcare illiteracy, we're paving the way for a more inclusive and accessible healthcare system.

Culture:

• 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.

• Conscious Leadership Values: https://conscious.is/15-commitments

https://vimeo.com/1188185714

Dearest is an equal opportunity employer committed to diversity and inclusion. We welcome applications from all qualified individuals, regardless of their background. Join us in transforming healthcare navigation.