Engineering Manager, Cloud Infrastructure

Upside Services, Inc.

Job Overview

Location

Austin

Job Type

Full-time

Full Job Description

📋 Description

• Lead a senior team of infrastructure engineers responsible for Upside’s core cloud platform, including compute, storage, networking, observability, and CI/CD capabilities that power all applications and data products.
• Spend approximately half your time on hands-on technical work—participating in code reviews, architecture design, and solving complex infrastructure problems alongside your team.
• Own the technical roadmap for Infrastructure, including leading two major 2026 initiatives: decomposing Upside’s single-region AWS environment into isolated, market-based cells for improved resilience and safer production validation, and building AI-assisted deployment tooling to enable R&D engineers to autonomously provision AWS infrastructure through guided automation.
• Ensure AWS environments are secure, cost-efficient, and production-ready by enforcing strong foundations in IAM, networking, secrets management, encryption, and compliance-aware controls.
• Drive improvements in developer experience across CI/CD pipelines, observability tooling, and platform services to empower product and data teams to ship, monitor, and operate services independently.
• Lead operational excellence initiatives focused on reliability, scalability, and performance, including capacity planning, incident management, on-call health, and post-incident learning.
• Partner with Product Security, Analytics Engineering, and AI Enablement teams to align infrastructure decisions with secure experimentation, scalable data systems, and safe AI adoption across R&D.
• Represent Infrastructure in cross-functional planning and technical forums, translating platform risks, tradeoffs, and technical constraints into clear business decisions.
• Establish a new model for technical leadership at Upside as the first Tech Lead Manager hire for Infrastructure, setting the standard for future engineering leadership roles.
• Support career growth and technical development of senior engineers who require peer-level technical guidance rather than oversight or micromanagement.
• Scale the role over time to include ownership of data infrastructure and potential stewardship of GCP as Upside expands its AI/ML investments.
• Maintain a team structure of approximately 8 direct reports, with a mix of full-time and contract staff, fostering a culture of autonomy, technical credibility, and execution focus.
• Operate in a flexible work environment with in-office employees eligible for lunch reimbursement, while supporting remote collaboration across teams.
• Contribute to a transparent culture with a mission-driven focus on transforming brick-and-mortar commerce through technology that delivers measurable value to consumers and retailers.

🎯 Requirements

• 5–7 years of hands-on AWS experience with deep fluency in compute (EC2, Lambda), databases (RDS, DynamoDB), IAM, networking, and secrets management
• 2–3 years managing infrastructure, platform, or SRE engineers, preferably a senior team where technical credibility was critical
• Strong command of Terraform for IaC and GitHub Actions or equivalent for deployment pipelines
• Background in DevOps or site reliability engineering with experience operating systems at scale
• Experience in environments with real security, compliance, or data sensitivity requirements, such as fintech or regulated industries handling sensitive consumer or financial data
• Comfort owning large-scale infrastructure programs that span multiple teams and require cross-functional coordination across R&D

🏖️ 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

DynamoDB

AWS

GCP

Terraform

DevOps

Onsite

$185k-215k

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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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