[Hiring] Principal Data Engineer @Upside

Role Description

We're looking for a Principal Data Engineer to be the technical backbone of our Analytics Engineering team. You'll architect and evolve the data platform that powers Upside's most critical product and business decisions: setting patterns, leading cross-functional workstreams, and raising the bar for how data moves through the company.

This is a role for someone who wants real ownership. Our team is small and intentional, our scope is large (~2,000 tables, 100 pipelines), and the work directly shapes product features, ML models, and business outcomes. If you do your best work when the problem is ambiguous and the impact is visible, this is the role for you.

Here are some ways you'll drive impact:

• Lead platform modernization; deprecate legacy workflows, migrate pipelines to scalable patterns, and sharpen our CI/CD and developer experience.
• Drive infrastructure and FinOps initiatives across Snowflake, Dagster, and dbt; reducing cost, improving governance, and increasing maintainability.
• Own platform evolution projects like making data consumable by agentic tools and workflows, and improving orchestration across the analytics stack.
• Design and deliver complex, domain-critical data products used by analysts, data scientists, and product teams to ship features and drive strategy.
• Architect reusable, extensible patterns for modeling, orchestration, and transformation; balancing flexibility, cost, and long-term maintainability.
• Lead technical planning across cross-functional teams, breaking down large data initiatives into scoped, sequenced workstreams.
• Mentor engineers, build internal documentation and tooling, and raise the overall standard for analytics engineering at Upside.
• Partner with engineering, product, data science, and business stakeholders to deliver end-to-end solutions.
• Represent Data Engineering in design forums and shape the future roadmap for data at Upside.

Qualifications

• 8+ years in data or analytics engineering with a track record of owning complex, business-critical systems end to end.
• Hands-on experience with AWS; deployments, workload management, cloud infrastructure and the modern data stack (Snowflake, dbt, Dagster, Databricks, Terraform).
• A track record of leading platform migrations, deprecations, or upgrades across shared systems; balancing technical risk, continuity, and long-term maintainability.
• Ability to design secure, reusable patterns for data ingestion, access control, and platform automation and comfort partnering with Infrastructure, Security, and Governance stakeholders.
• Experience with DevOps practices (CI/CD for data), data governance, or FinOps.
• Ability to break down ambiguous, cross-functional problems and lead implementation from design to deployment.
• Clear communication across all audiences; engineers, analysts, product managers, and business leaders.
• A genuine drive to mentor others, set standards, and leave every system better than you found it.

Requirements

• Experience supporting ML workflows; building features or monitoring model inputs and outputs.
• Background in a fast-growing startup or on platform-style teams that serve internal customers.

Benefits

• Medical, dental, and vision coverage starting on Day 1.
• Equity (ISOs).
• 401(k) program.
• Family planning programs + paid parental leave.
• Physical fitness and wellness memberships.
• Emotional and mental health support programs.
• Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break.
• Flexible work environment.
• Lunch reimbursement for in-office employees.
• Employee Resource Groups.
• Learning and Development stipend.
• Transparent culture.
• Amazing mission!