Upside Services, Inc. logo

Principal Data Engineer

Job Overview

Location

DC

Job Type

Full-time

Category

Software Engineering

Date Posted

June 24, 2026

Full Job Description

đź“‹ Description

  • • Lead the architecture and evolution of Upside’s data platform, which supports ~2,000 tables and 100 pipelines powering critical product, business, and ML decisions.
  • • Deprecate legacy data workflows and migrate pipelines to scalable, modern patterns using Snowflake, dbt, and Dagster to improve maintainability and reduce technical debt.
  • • Drive FinOps initiatives across the data stack to reduce cloud costs, enhance governance, and increase operational efficiency.
  • • Own platform modernization projects including enabling data consumption by agentic tools and improving orchestration across the analytics ecosystem.
  • • Design and deliver complex, domain-critical data products used by analysts, data scientists, and product teams to ship features and inform business strategy.
  • • Architect reusable, extensible patterns for data modeling, transformation, and orchestration that balance flexibility, cost, and long-term maintainability.
  • • Lead technical planning across cross-functional teams, breaking down large-scale data initiatives into scoped, sequenced workstreams with clear deliverables.
  • • Mentor data engineers, build internal documentation and tooling, and raise the overall standard for analytics engineering practices at Upside.
  • • Partner with engineering, product, data science, and business stakeholders to deliver end-to-end data solutions aligned with organizational goals.
  • • Represent Data Engineering in cross-functional design forums and actively shape the future roadmap for data infrastructure and governance.
  • • Champion quality upstream by advocating for early testing, validation, and robust data pipelines to prevent downstream failures.
  • • Implement and improve DevOps practices for data, including CI/CD pipelines, observability, and automation to reduce toil and increase reliability.
  • • Collaborate with Infrastructure, Security, and Governance teams to design secure, scalable patterns for data ingestion, access control, and platform automation.
  • • Communicate technical concepts clearly to engineers, analysts, product managers, and business leaders to ensure alignment and confident decision-making.
  • • Foster a culture of continuous improvement by setting standards, documenting best practices, and leaving systems better than found.

🎯 Requirements

  • • 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, and modern data stack tools (Snowflake, dbt, Dagster, Databricks, Terraform)
  • • Proven experience leading platform migrations, deprecations, or upgrades across shared systems while balancing technical risk and continuity
  • • Demonstrated ability to design secure, reusable data patterns and partner with Infrastructure, Security, and Governance stakeholders
  • • Experience with DevOps practices for data (CI/CD), data governance, and FinOps
  • • Ability to break down ambiguous, cross-functional problems and lead implementation from design to deployment

🏖️ 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 + 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

Skills & Technologies

AWS
Terraform
Senior
Remote
$215k-250k

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Upside Services, Inc. logo
Upside Services, Inc.
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About Upside Services, Inc.

Upside Services provides a cash-back platform that connects consumers with nearby fuel stations, grocery stores, and restaurants. The company earns revenue through performance-based marketing agreements with merchants, who pay only when Upside drives incremental profit above baseline sales. The mobile app delivers personalized offers and processes rebates to users’ bank accounts or digital wallets. Founded in Washington, D.C., Upside uses anonymized transaction data and machine-learning models to forecast demand and set dynamic incentives, aiming to increase foot traffic and basket size for partner businesses while rewarding consumer loyalty.

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