Engineering Manager, Upside
Cloud Infrastructure
$185-215k
+ Equity
Mobile reward application for retail spending
Be an early applicant
Mobile reward application for retail spending
201-500 employees
Be an early applicant
$185-215k
+ Equity
201-500 employees
Company mission
To advance the economic power of people living and working in the real world.
Role
Who you are
- 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; ideally a senior team where technical credibility mattered as much as people skills
- Strong command of Terraform for IaC and GitHub Actions or equivalent for deployment pipelines
- Background in DevOps or site reliability engineering; you understand what it means to operate systems at scale and build cultures of operational excellence
- Experience in environments with real security, compliance, or data sensitivity requirements; fintech, regulated industries, or companies handling sensitive consumer or financial data
- Comfort owning large-scale infrastructure programs that span multiple teams and require coordination across R&D, not just execution within your own team
- Eagerness to integrate AI and automation into infrastructure workflows; not as a future interest, but as something you're actively thinking about now
What the job involves
- We're looking for an Engineering Manager to lead our Infrastructure team; the group responsible for Upside's core cloud platform, networking, security, and foundational services
- This team provides the compute, storage, networking, observability, and CI/CD capabilities that power every application and data product at Upside
- This is a Tech Lead Manager role
- You'll spend roughly half your time doing hands-on technical work alongside your team and half driving execution, cross-functional coordination, and people leadership
- The team is senior and self-directed; they don't need oversight, they need a technically credible leader who can go deep with them and take on the hard infrastructure problems
- 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: a cell-based architecture initiative to decompose Upside's single-region AWS environment into isolated, market-based cells for improved resilience and safer production validation; and AI-assisted deployment tooling to reduce the volume of infrastructure requests by enabling engineers across R&D to deploy AWS infrastructure themselves through guided automation
- Ensure Upside's AWS environments are secure, cost-efficient, and production-ready, with strong foundations in IAM, networking, secrets management, encryption, and compliance-aware controls
- Drive developer experience improvements across CI/CD, observability, and platform tooling, making it easier and safer for product and data teams to ship, monitor, and operate services independently
- Drive operational excellence across reliability, scalability, and performance; including capacity planning, incident management, on-call health, and post-incident learning
- 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, translating platform risks and tradeoffs into clear business decisions
- You want to go deep, not just manage. This role is structured so that nearly half your time is hands-on technical work...you'll be in the code, in the architecture reviews, and in the weeds on the problems that matter most
- You're joining at a moment when the work is real and the roadmap is set. Cell-based architecture and AI-assisted deployment tooling are active priorities, not future-state ideas. You'll be leading both from day one
- You'll set a new pattern for R&D at Upside. This is the first Tech Lead Manager hire of its kind here...you're not backfilling a role, you're establishing what technical leadership looks like for infrastructure going forward
- The team are senior, capable engineers who want a technical peer and execution leader not someone to direct their work. If you've wanted to lead a high-caliber team without spending all your time in 1:1s and status updates, this is it
- The scope grows with you. Over time this role has a natural path toward data infrastructure ownership and GCP stewardship as Upside's AI/ML investment expands
Our take
Loyalty systems, vouchers, and other special offers have a proven track record at winning over new customers for businesses. However, customers can be reluctant to sign up due to the sheer number of these schemes. Upside exists to unify these loyalty schemes with a single flexible reward app.
While retail reward platforms are nothing new, Upside functions more like a marketplace, linking participating businesses to potential customers. It also rewards customers with cash back on eligible purchases, a more flexible reward than is traditional in loyalty schemes.
With over 50,000 businesses enrolled and 30 million app users, Upside has grown into a major player in this sector. The company is well-funded and ever-expanding its offering, with a product that is increasingly appreciated by consumers in an expensive world, as well as the businesses who depend on their custom.
Freddie
Company Specialist at Welcome to the Jungle
Insights
24% employee growth in 12 months
Company
Funding (1 round)
Apr 2022
$65m
SERIES D
Total funding: $65m
Company benefits
- Health and Wellness - We’re happy to provide our team members with generous health, vision, and dental insurance options
- Lunch - We cover the cost of lunch everyday for team members onsite to enhance our team building and encourage collaboration. Plus local restaurants appreciate it!
- Stock Options - Our team’s success is our company’s success, and we should all have a stake in that. We’re glad to offer our team members valuable stock options
- Unlimited PTO - Yes, you read that right. When you need time off, we’ve got you covered
Company HQ
Dupont Circle, Washington, DC
Leadership
Alex Kinnier
(CEO & Co-Founder)Experience as Group Product Manager for Google from 2005 to 2008. Senior Vice President of Products and Engineering for Opower from 2012 to 2015.
Wayne Lin
(CPO & Co-Founder)Experience as Product Manager for Google from 2005 to 2010. Vice President of Product Management & Analytics for Opower from 2010 to 2015.
Rick McPhee
(Co-Founder)Experience as Vice President of Engineering for HP's Fortify Software from 2008 to 2012. Senior Vice President of Engineering for Opower from 2012 to 2015.
Joanna Kochaniak
(Engineer & Co-Founder)Experience as Programmer Analyst for the Institute for Physical Sciences from 2007 to 2010. Lead Software Engineer for Opower from 2010 to 2015.
Jan Rubio
(Designer & Co-Founder)Experience as Research Assistant for George Washington University from 2009 to 2011. Senior Software Engineer for Opower from 2011 to 2016.
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