Engineering Manager, Cloud Infrastructure

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retailprofit measurement attribution and incrementalityto provide users with more value on their everyday purchases and brick-and-mortar businesses with new profitable customers. Weve 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:

Were looking for an Engineering Manager to lead our Infrastructure team; the group responsible for Upsides 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. Youll 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 dont 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 Upsides 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 Upsides 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 be in the code in the architecture reviews and in the weeds on the problems that matter most.

• Youre 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. Youll be leading both from day one.

• Youll set a new pattern for R&D at Upside. This is the first Tech Lead Manager hire of its kind not backfilling a role youre 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 youve 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 Upsides AI/ML investment expands.

Ideal Qualifications

• 57 years of hands-on AWS experience with deep fluency in compute (EC2 Lambda) databases (RDS DynamoDB) IAM networking and secrets management.

• 23 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 youre 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 $185000 - $215000 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 during the hiring process.

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 our 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!

Diversity and Inclusion:

Diversity drives innovation and our differences make us stronger. Were passionate about building a workplace that represents a variety of backgrounds skills and perspectives and we do not discriminate based on race religion color national origin gender sexual orientation age marital status veteran status or disability status. Everyone is welcome here!

If theres anything we can do to support a disability or special need during your application or interview process please email

This email is for accessibility accommodations only it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies:

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for and will not pay placement fees for candidates submitted by any party or agency other than its approved recruitment partners.

Required Experience:

Manager