Staff Software Engineer

DataRobot•Boston, ON

About The Position

DataRobot delivers AI that maximizes impact and minimizes business risk. Our platform and applications integrate into core business processes so teams can develop, deliver, and govern AI at scale. DataRobot empowers practitioners to deliver predictive and generative AI, and enables leaders to secure their AI assets. Organizations worldwide rely on DataRobot for AI that makes sense for their business — today and in the future. DataRobot’s Fleet team is the engine behind how our platform runs across all customer environments—multi-tenant SaaS, single-tenant SaaS, VPC, and on-prem deployments. We build and operate the foundational Kubernetes infrastructure that powers everything from CI/CD to service orchestration and deployment at scale. We support a wide variety of deployment models—from SaaS to on-prem - using a Kubernetes-native approach and modern toolset. Our mission is to unify how we build, deploy, and operate the platform across environments while improving resilience, maintainability, and developer velocity. The next 1–2 years will be transformative for the Fleet team. We’re laying the groundwork to enable unified deployment experiences, zero-downtime upgrades, and intelligent platform automation—while lowering Total Cost of Ownership (TCO) and boosting developer velocity. That’s where you come in. As a Staff Software Engineer, you’ll be responsible for technical leadership and vision. You’ll lead by example—rolling up your sleeves as a technical contributor to solve complex problems, shaping architecture, and mentoring engineers to do their best work and advance their careers. You’ll work across our control plane systems, influence cross-team roadmaps, and bring pragmatic engineering practices into how we build, test, and operate infrastructure software. This is not a “stay in your swim lane” role. You’ll question assumptions, challenge complexity, and help drive a high-performance culture. You’ll be trusted to bring clarity where there’s ambiguity, and momentum where there’s inertia. This role includes participation in an on-call rotation—we believe in shared ownership of our platform and aim to build systems that are resilient, observable, and require minimal intervention.

Requirements

7-10+ years of engineering experience, with at least 5+ in infrastructure, platform, or backend systems roles.
Deep expertise in Kubernetes internals and operations, including networking, scheduling, scaling, and controller patterns.
Proven ability to design and build systems from scratch, making pragmatic tradeoffs along the way.
Strong proficiency in modern programming languages such as Python or Go.
Experience building production-quality, reliable, and observable systems that are used across engineering organizations.
A growth-oriented mindset—driven to teach, learn, and improve systems as well as people.
Experience operating across multiple cloud providers (AWS, GCP, Azure) and/or hybrid environments.
Strong experience with Helm, container orchestration patterns, and CI/CD automation.
Comfortable working with IaC (Terraform, Pulumi) and GitOps workflows.
Ability to influence without authority and align diverse stakeholders around technical decisions.

Nice To Haves

Familiarity with Cilium, Kyverno, KEDA, Gateway API, OPA, or similar technologies.
Experience building and running multi-tenant SaaS platforms.
Exposure to on-prem delivery models or regulated environments.
Experience with performance tuning for large-scale data or compute workloads.
Past success driving infrastructure transformation or decomposing legacy systems.
Experience working with GPU infrastructure for training and inference.

Responsibilities

Architect and implement scalable, secure Kubernetes-based infrastructure for multi-cloud and hybrid environments.
Lead technical direction for core Fleet initiatives—control plane services, tenancy models, deployment pipelines, observability layers, and more.
Mentor engineers across the team, fostering a strong engineering culture of ownership, curiosity, and excellence.
Drive modernization efforts—introducing patterns like GitOps, Policy-as-Code (Kyverno), Cilium networking, autoscaling, and better resource efficiency.
Collaborate deeply with SRE, Platform, and Application teams to align infrastructure capabilities with real-world product demands.
Champion best practices in CI/CD, reliability, container lifecycle management, and dev experience.
Be a thought partner to engineering leadership and help shape how Fleet scales its impact across the company.