Jobs › Project44

Senior Software Engineer - DevOps/SRE

Project44 · Chicago, IL · Engineering

Posted Sep 11, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you designed infrastructure that had to stay highly available and fault-tolerant under real production load. What broke, and what did you learn?

What they are checking: hands-on experience building resilient systems, not just theoretical knowledge

Describe a major incident you were the escalation point for. What was the root cause, and what changed afterward so it didn't happen again?

What they are checking: real incident command experience and follow-through on remediation, not just firefighting

Tell me about a time you had to push back on a security requirement, like secrets management or network segmentation, because it conflicted with a delivery deadline. How did that get resolved?

What they are checking: how they balance compliance obligations like SOC 2 or ISO 27001 against engineering pressure

How have you mentored mid-level or senior engineers on your team, and can you give an example of a design or code review where your feedback changed the outcome?

What they are checking: actual technical leadership ability versus just seniority by tenure

Tell me about a time you introduced a new tool or platform to modernize an infrastructure stack. How did you get buy-in from teams who were comfortable with the old way?

What they are checking: change management skills and ability to drive adoption across skeptical engineering teams

What would you do

Say our CI/CD pipeline is slowing down dozens of engineering teams because deploys are unsafe and flaky. Where do you start, and how do you measure whether it's actually getting better?

What they are checking: ability to diagnose systemic delivery problems and use metrics rather than gut feel to prove improvement

If cloud spend was flagged as too high this quarter, how would you find savings without quietly making the system less reliable?

What they are checking: whether cost optimization instincts are balanced against production risk

About the work

Walk me through how you'd set the technical direction for our cloud infrastructure across AWS and GCP if you found teams using inconsistent patterns for compute, networking, and storage.

What they are checking: whether the candidate can establish and drive adoption of a coherent infra strategy rather than just executing tickets

How do you think about infrastructure-as-code standards, and what's your experience with Terraform or Pulumi at a scale where multiple teams are contributing to the same modules?

What they are checking: depth with IaC tooling and whether they've dealt with shared-ownership problems, not just solo scripting

What does a good GitOps workflow look like to you, and where have you seen it go wrong?

What they are checking: whether GitOps is a buzzword or something they've actually operated and debugged

How do you define SLOs and SLIs for a real-time, high-throughput data platform, and how do you decide when they're too strict or too loose?

What they are checking: practical judgment on reliability targets versus copying textbook definitions

What's your experience with Kubernetes at scale, and what's the trickiest cluster or workload problem you've had to solve?

What they are checking: real depth of container orchestration knowledge beyond surface-level familiarity

Walk me through your monitoring and observability stack in a past role, from metrics collection to alerting to what an on-call engineer actually sees at 3am.

What they are checking: end-to-end thinking about observability rather than naming tools without context

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The full job description

As published by Project44.

&nbsp; &nbsp; &nbsp; Why project44? &nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">&nbsp; At project44, we believe in better. &nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">&nbsp; We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world.&nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">&nbsp; With our Decision Intelligence Platform, Movement , we’re redefining how global supply chains operate. By transforming fragmented logistics data into real-time, AI-powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next-gen applications that keep businesses moving forward.&nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">&nbsp; Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India we are powered by a diverse&nbsp;global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose.&nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">&nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">AI at project44 <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">We expect every project44 team member, regardless of role or function, to actively leverage AI in their day-to-day work. Whether you're building product, serving customers, managing people, or running operations, AI is a tool you're expected to use with intent, curiosity, and judgment. We don't expect everyone to be a data scientist. We do expect everyone to be an intelligent user of AI: able to identify where it adds value, direct it effectively, evaluate outputs critically, and govern it responsibly. We invest in our team's AI fluency because we believe it's a competitive advantage for every person at project44, not just our engineers If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high-performance team – we should talk. <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":0,"335551620":0,"335559738":240,"335559739":240}">&nbsp; The Role &nbsp; project44 is looking for a Senior&nbsp; DevOps/SRE/Platform&nbsp; Engineer to join our&nbsp; Foundations Engineering&nbsp; team. You will work in a fast-paced Agile environment designing, building, and&nbsp; operating &nbsp;the foundational systems that power project44's global&nbsp; logistics &nbsp;network—ensuring our platform is reliable, observable, cost-efficient, and built to scale. This is a high-ownership, high-impact role at the intersection of cloud infrastructure, distributed systems, and developer enablement. <span class="EOP Selected SCXW24037269 BCX8" data-ccp-props="{"134233117":true,"134233118":true,"201341983":0,"335559740":240}">&nbsp; Key Accountabilities: What&nbsp;you'll&nbsp;work on &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="1" data-aria-level="1"> Design, build, and&nbsp;operate&nbsp;core infrastructure across our primary GCP environment and secondary AWS footprint,&nbsp;leveraging&nbsp;managed services to deliver scalable, reliable, and cost-effective solutions &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="2" data-aria-level="1"> Own and evolve our Kubernetes (GKE) platform—cluster lifecycle management, node pool strategy, networking, RBAC, and workload reliability—ensuring developer teams can ship safely and quickly &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="3" data-aria-level="1"> Build and&nbsp;maintain&nbsp;Terraform-based infrastructure-as-code across cloud environments, enforcing standards for modularity, state management, and repeatable, auditable provisioning &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="4" data-aria-level="1"> Manage and improve our Kafka and&nbsp;Strimzi&nbsp;streaming infrastructure, supporting high-throughput event pipelines that are foundational to project44's real-time data capabilities &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="5" data-aria-level="1"> Lead and execute cost optimization initiatives—rightsizing compute, improving resource&nbsp;utilization, reducing waste, and creating visibility and accountability for cloud spend across engineering teams &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="6" data-aria-level="1"> Champion observability and reliability practices — SLOs/SLIs, incident response, on-call processes, and postmortems — to reduce MTTR and prevent recurrence. <span data-ccp-props="{"134233117":true,"134233118":true,"201341983":0,"335557856":16777215,"335559740":240}">&nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="7" data-aria-level="1"> Partner with application engineering teams to define and implement platform standards for deployment, scaling, service mesh, secrets management, and infrastructure security &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="8" data-aria-level="1"> Participate in a team on-call rotation, debugging and resolving infrastructure and platform incidents with urgency and rigor &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="9" data-aria-level="1"> Contribute to technical design discussions, architecture reviews, and documentation—helping set a high bar for quality, reliability, and operational excellence across the engineering organization &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="10" data-aria-level="1"> Mentor and support other engineers through code reviews, pairing, and technical guidance &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="11" data-aria-level="1"> Evaluate and introduce new tools, platforms, and automation to continuously modernize the infrastructure stack. <span data-ccp-props="{"134233117":true,"134233118":true,"201341983":0,"335557856":16777215,"335559740":240}">&nbsp; <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="12" data-aria-level="1"> Drive cost-optimization initiatives across cloud spend without compromising reliability or performance. <span data-ccp-props="{"134233117":true,"134233118":true,"201341983":0,"335557856":16777215,"335559740":240}">&nbsp; &nbsp; Qualities &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="2" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="1" data-aria-level="1"> Strong communication&nbsp;skills, with the ability to clearly explain infrastructure decisions through design docs, postmortems, and cross-functional discussions, and collaborate effectively with both technical and non-technical partners &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="2" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="2" data-aria-level="1"> A strong analytical approach to problem-solving, with comfort navigating ambiguity and making tradeoffs explicit—especially across reliability, velocity, and cost &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="2" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="3" data-aria-level="1"> A sense of ownership, curiosity, and resilience—comfortable voicing ideas, incorporating feedback, and iterating toward better solutions &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="2" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="4" data-aria-level="1"> A platform-minded builder who thinks about the engineers and systems they enable, not just the infrastructure they manage &nbsp; &nbsp; Qualifications &nbsp; • 5+ years of professional experience in platform engineering, infrastructure engineering, SRE, DevOps, or a closely related role &nbsp; Strong experience in: &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="1" data-aria-level="1"> Kubernetes administration and operations at scale (GKE strongly preferred), including cluster networking, autoscaling, workload isolation, and upgrade management &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="2" data-aria-level="1"> Kafka operations and architecture, including topic design, consumer group management, broker configuration, and integration with streaming workloads (Strimzi&nbsp;experience a plus) &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="3" data-aria-level="1"> Infrastructure-as-code using Terraform—module design, state management, CI-driven plan/apply workflows, and drift detection &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="4" data-aria-level="1"> Google Cloud Platform (GCP) across core services: GKE, GCS, Cloud NAT, VPC networking, IAM, Artifact Registry, and related managed services &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="5" data-aria-level="1"> Cloud observability tooling and practices—building meaningful dashboards, alerts, SLI/SLO frameworks, and runbooks regardless of the tool stack &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="6" data-aria-level="1"> Cloud networking fundamentals: VPCs, subnetting, private connectivity, DNS, load balancing, and security group/firewall&nbsp;design &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="3" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="7" data-aria-level="1"> Cloud cost management:&nbsp;identifying&nbsp;and executing on optimization opportunities, building spend visibility, and influencing engineering behavior around resource efficiency &nbsp; Desirable and helpful (but not necessary): &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="1" data-aria-level="1"> Experience with AWS services alongside a primary GCP environment &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="2" data-aria-level="1"> Scripting or automation in Python, Go, Bash, or similar for operational tooling &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="3" data-aria-level="1"> Experience with service mesh technologies (Istio,&nbsp;Linkerd) or advanced Kubernetes networking (Cilium, Calico) &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="4" data-aria-level="1"> Familiarity with CI/CD systems and&nbsp;GitOps&nbsp;patterns (ArgoCD, Flux, or similar) &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="5" data-aria-level="1"> Experience building or operating developer platform capabilities (internal developer platforms, golden paths, self-service provisioning) &nbsp; <li data-leveltext="" data-font="Symbol" data-listid="4" data-list-defn-props="{"335552541":1,"335559685":720,"335559991":360,"469769226":"Symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}" data-aria-posinset="6" data-aria-level="1"> Using AI-assisted development tools for infrastructure automation, runbook generation, or operational tooling (e.g., Claude, GitHub Copilot, or similar) &nbsp; Work Authorization: Candidates must be authorized to work in the US without current or future employer-sponsored visa support. <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":6,"335551620":6,"335559738":240,"335559739":240}"> In-office Commitment: &nbsp; <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":6,"335551620":6,"335559738":240,"335559739":240}">Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed&nbsp;to joining our team on-site, <span data-ccp-props="{"134233117":false,"134233118":false,"335551550":6,"335551620":6,"335559738":240,"335559739":240}"> &nbsp; in our beautiful headquarters 3 days a week . Together, we’re building something extraordinary—learn, grow, and thrive in our fast-paced, transformative environment. We continually evaluate our pay ranges to reflect skills, experience, and market conditions. The base salary offered will be determined by assessing a candidate's experience and skills relative to the scope and responsibilities of the position, as well as the specific geographic location where the job will be performed. Base salary is one component of project44's total compensation package, which also includes stock options for all EOR and project44-employed team members, bonus or commission eligibility depending on role, and a benefits package tailored to your country of employment. Specific benefits package offerings vary by country and may include health, dental, and vision coverage, retirement plans, and paid time off, in line with local market standards and statutory programs. The base salary range for this position is USD 130,000 – USD 190,000 Diversity & Inclusion &nbsp; At project44,&nbsp;we're&nbsp;designing the future of how the world moves. As we work to deliver a truly world-class product,&nbsp;we're&nbsp;intentionally building teams that reflect the unique communities we serve.&nbsp;We're&nbsp;focused on creating a company where all team members can bring their authentic&nbsp;selves&nbsp;to work every day. &nbsp; project44 is an equal opportunity employer. If you share our values and passion for the future of&nbsp;logistics,&nbsp;we'd&nbsp;love to review your application. Even if you&nbsp;don't&nbsp;meet 100% of the requirements, please consider applying — studies show you can still be a strong candidate at 50%. &nbsp; For any accommodation needed during the hiring process, please email recruiting@project44.com. &nbsp; &nbsp; &nbsp; &nbsp;

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