Upside is a nationally scalable housing stability platform that partners with health plans and employers to identify and stabilize people experiencing housing instability.
Meet Upside: We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives. About the role: 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. In addition to the leadership responsibilities above, you will: - 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. Why You Should Apply - 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. Ideal Qualifications - 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. Engineering Culture: We want our engineering leaders to be able to make thoughtful, impactful technical decisions while also having the space to coach their engineers and support their growth. We ask our managers to focus on a team of around 8 direct reports, while our more senior managers may operate across two teams. The staffing for these reports is always split - we see incredible value from a mix of full-time and contract staff. Compensation: The US base salary range for this full-time position is $185,000 - $215,000+ equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range d