Upside

Cloud Engineer

• Lead a senior team of infrastructure engineers, providing technical guidance, career support, and the execution leadership needed to ship high-impact platform work reliably and on time.
• Own the technical roadmap for Infrastructure, including two major programs launching in 2026.
• Ensure Upside's AWS environments are secure, cost-efficient, and production-ready.
• Drive developer experience improvements across CI/CD, observability, and platform tooling.
• Drive operational excellence across reliability, scalability, and performance.
• Partner closely with Product Security, Analytics Engineering, and AI Enablement to ensure infrastructure decisions support reliable experimentation, scalable data systems, and safe AI adoption across R&D.
• Represent Infrastructure in cross-functional planning and technical forums.

Engineering Manager, Cloud Infrastructure

Engineer

• Leverage AI tools to design and deliver scalable security solutions that address application vulnerabilities
• Execute automated security testing (SAST, SCA) and work directly with engineers to resolve findings
• Develop threat models and collaborate with product and engineering teams to surface, document, and prioritize risk
• Advise leadership on security architecture decisions and application security best practices
• Build developer security literacy through training, enablement, and vulnerability management guidance
• Participate in penetration testing efforts and support bug bounty program operations
• Contribute to the administration of AWS Control Tower and IAM provisioning workflows
• Stay current with the broader security community and bring emerging trends back to the team

Staff AppSec Engineer

Data Engineer

• 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

Principal Data Engineer

General Counsel

• Provide legal guidance across many subject areas, including contract law, privacy, data protection, consumer protection laws, employment, and commercial litigation
• Oversee contract review and execution process for the entire company
• As needed, draft and negotiate the largest commercial contracts with merchant partners, data providers, and vendors
• Leverage AI to drive productivity and efficiency on legal matters across the company
• Work with and manage our outside counsel firms

Product Designer

• Own the quality, consistency, and polish bar across the consumer and payments experience.
• Lead a small, tightly knit team of designers and researchers embedded in delivery pods; systematically grow their craft and how the team operates.
• Architect cohesive design systems and frameworks across fragmented journeys and surfaces — balancing design integrity against iteration speed.
• Partner with Product, Engineering, and Marketing to pull design into discovery and drive measurable outcomes across onboarding, discovery, redemption, and retention.
• Deepen the research practice and its integration into decision-making.
• Apply an AI-native approach to how design and research scale.

Head of Design and Research

Infrastructure Engineer

• Lead with platform and company outcomes over local optimization. You lean in wherever critical infrastructure risk or opportunity exists, regardless of org boundaries, and prioritize the success of the broader platform and product ecosystem.
• Create a safe, collaborative team environment. You name problems, invite open discussion, and help your team learn from incidents and change without blame.
• Raise the bar. You identify and influence improvements in reliability, performance, security, and engineering standards across services and environments.
• Provide clarity and empower autonomy. You ensure expectations, SLAs, and guardrails are clear so teams can move quickly and independently on a stable platform.
• Ensure our AWS environments are secure, cost-efficient, and production-ready, with strong foundations in IAM, networking, secrets management, encryption, and compliance-aware controls.
• Lead the evolution of our CI/CD, observability, and platform tooling, making it easier and safer for product and data teams to ship, monitor, and operate services independently, and improving overall developer experience.
• Drive operational excellence across reliability, scalability, and performance, including capacity planning, incident management, on-call health, and post-incident learning culture.
• Define and track key platform health and cost metrics, such as availability, latency, error budgets, infrastructure cost per transaction, and change failure rates, using these insights to guide prioritization and continuous improvement.
• Partner closely with Security, Data Platform, and Product Engineering teams to ensure infrastructure decisions enable reliable experimentation, user-centric product development, and scalable data and ML systems.
• Oversee large-scale programs that span multiple teams, such as cloud modernization, multi-region or cell-based architecture, and foundational security or resilience upgrades.
• Represent Infrastructure in cross-functional planning and technical forums, translating platform risks and opportunities into clear business tradeoffs and decisions.

Manager, Infrastructure Engineering

Architect

• Own and steward the R&D Operating Blueprint — keep it current as the organization evolves, run periodic health checks, and make redesign calls when something isn't working
• Lead operating rhythm work: forum design, cadence changes, redesigns, and post-mortems — the ongoing drumbeat of keeping the operating model healthy
• Serve as the internal expert on AI-native process design — the go-to voice for "how do we build this as a system, not a document"