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Senior Software Engineer

Project44 · Chicago, IL · Engineering

Posted Sep 11, 2026 · We last checked this listing on Sep 20, 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.

Behavioral

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?

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?

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?

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?

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?

change management skills and ability to drive adoption across skeptical engineering teams

Technical

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.

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?

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?

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?

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?

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.

end-to-end thinking about observability rather than naming tools without context

Situational

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?

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?

whether cost optimization instincts are balanced against production risk

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The full job description

As published by Project44.

<div class="content-intro">     </div>Why project44?   At project44, we believe in better.   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.   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.   Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose.   AI at project44 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.  The Role  <div>project44 is looking for a Senior Devops Engineer to join our engineering team. You will work in a fast-paced Agile environment designing, building, and implementing best-in-class integrations to accelerate how project44 connects to the world’s logistics networks.</div> <div> What You'll Do <ul> <li>Set technical direction for cloud infrastructure strategy across AWS/GCP, including compute, networking, storage, and Kubernetes-based container orchestration.</li> <li>Design, build, and maintain highly available, fault-tolerant infrastructure supporting a high-throughput, real-time data platform.</li> <li>Lead the evolution of CI/CD pipelines to improve deployment velocity, safety, and developer experience across dozens of engineering teams.</li> <li>Own infrastructure-as-code standards (Terraform, Pulumi, or similar) and drive adoption of GitOps practices.</li> <li>Champion observability and reliability practices — SLOs/SLIs, incident response, on-call processes, and postmortems — to reduce MTTR and prevent recurrence.</li> <li>Partner with Security to embed guardrails for secrets management, network segmentation, vulnerability remediation, and compliance (SOC 2, ISO 27001, etc.).</li> <li>Mentor and provide technical leadership to mid-level and senior DevOps/SRE engineers; conduct design and code reviews.</li> <li>Drive cost-optimization initiatives across cloud spend without compromising reliability or performance.</li> <li>Act as an escalation point for major incidents, driving root-cause analysis and long-term remediation.</li> <li>Evaluate and introduce new tools, platforms, and automation to continuously modernize the infrastructure stack.</li> </ul> </div> <div> What You'll Bring <ul> <li>6+ years of experience in DevOps, Site Reliability Engineering, or Infrastructure Engineering roles, including experience leading technical initiatives.</li> <li>Deep expertise with a major cloud provider (AWS preferred; GCP or Azure also relevant) and container orchestration (Kubernetes, ECS, or similar).</li> <li>Strong hands-on experience with infrastructure-as-code (Terraform, CloudFormation, or Pulumi) and configuration management tools.</li> <li>Proven track record building and scaling CI/CD pipelines (e.g., Jenkins, GitHub Actions, GitLab CI, CircleCI, ArgoCD).</li> <li>Solid scripting/programming ability in Python, Go, or Bash for automation and tooling.</li> <li>Experience building and operating complex distributed systems</li> <li>Proficient in high level script languages such as Python or Groovy</li> <li>Experience developing solutions leveraging Docker</li> <li>Experience managing Linux (Ubuntu) systems</li> <li>Configuration management experience with Ansible or Terraform</li> <li>Building/implementing monitoring for network, server, application, and database layers</li> <li>Experience with monitoring tools such as Zabbix, Nagios, Grafana, CloudWatch</li> <li>Experience with APM tools such as New Relic, AppDynamics, Datadog, Runscope</li> <li>Experience with log aggregation systems using Logstash and Elasticsearch</li> <li>Continuous integration, testing, and deployment using git, Jenkins</li> <li>Experience with relational databases (Postgres)</li> </ul> </div> Work Authorization: Candidates must be authorised to work in the US without current or future employer-sponsored visa support. In-office Commitment: Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on-site, 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 USD130,000 – USD190,000 Diversity & Inclusion  At project44, we're designing the future of how the world moves. As we work to deliver a truly world-class product, we're intentionally building teams that reflect the unique communities we serve. We're focused on creating a company where all team members can bring their authentic selves to work every day.  project44 is an equal opportunity employer. If you share our values and passion for the future of logistics, we'd love to review your application. Even if you don't meet 100% of the requirements, please consider applying — studies show you can still be a strong candidate at 50%.  For any accommodation needed during the hiring process, please email recruiting@project44.com.   <div class="content-conclusion">   </div>

Apply at Project44

Senior Software Engineer

Likely interview questions for this role

Practice this interview out loud.

The full job description

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