Senior Site Reliability Engineer

Penninteractive; Canada; Remote; CAD 145,000 - 193,000; Full time

Benefits offered by this job

Competitive compensation

Comprehensive benefits

Relaxed work environment

Education & conference reimbursements

Job summary

PENN Entertainment’s SRE team is seeking a Senior Site Reliability Engineer to own infrastructure for a large-scale sports betting and media platform. You’ll drive migrations, build tooling with ArgoCD/Helm, and improve observability across production services in multiple jurisdictions.

You’ll lead cross‑team projects, mentor teammates, and bring a production‑first approach to architecture decisions in a fast‑paced, autonomy‑driven environment.

Qualifications

• 5+ years of experience in DevOps / SRE roles.
• Experience operating Kubernetes in production environments.
• Experience with AWS, GCP, and/or on‑prem environments.
• Proficiency in Go, Python, or Bash for building tooling.
• Deep understanding of distributed systems, failures, capacity planning and performance.
• Experience with GitOps and CI/CD workflows (ArgoCD, Helm, GitHub Actions, or similar).
• Experience with infrastructure‑as‑code (Terraform, Helm, or equivalent).
• Track record of leading complex migrations or cross‑team projects.
• Strong incident response and structured debugging skills.
• Clear technical communication and documentation skills.

Responsibilities

• Lead complex infrastructure migrations across environments and jurisdictions.
• Build and maintain platform tooling and automation (ArgoCD, Helm, GitHub Actions).
• Support development teams and unblock cross‑team dependencies.
• Design observability and alerting with Datadog dashboards and runbooks.
• Provide on‑call support and incident response to maintain platform reliability.

Skills

Kubernetes expertise

AWS/GCP

Go/Python/Bash

GitOps

IaC (Terraform/Helm)

Distributed systems

Incident response

Technical writing

Tools

ArgoCD

Helm

GitHub Actions

Terraform

Datadog

Job description

PENN Entertainment, Inc. is North America’s leading provider of integrated entertainment, sports content, and casino gaming experiences. From casinos and racetracks to online gaming, sports betting and entertainment content, we deliver the experiences people want, how and where they want them.

We’re always on the lookout for those who are passionate about creating and delivering cutting‑edge online gaming and sports media products. Whether it’s through Hollywood Casino, theScore Bet Sportsbook, or theScore media app, we’re excited to push the boundaries of what’s possible. These state‑of‑the‑art platforms are powered by proprietary in‑house technology, a key component of PENN’s omnichannel gaming and entertainment strategy.

When you join PENN Entertainment’s digital team, you’ll not only work on these cutting‑edge platforms through theScore and PENN Interactive, but you’ll also be part of a company that truly cares about your career growth. We’re committed to supporting you as you expand your skills and explore new opportunities.

With locations throughout North America, you can build a future at PENN Entertainment wherever you are. If you want to challenge conventions in gaming, media and entertainment, we want to talk to you.

About the Role& Team

The SRE team at PENN Entertainment is looking for a Senior Site Reliability Engineer to help build and operate the infrastructure behind a large-scale sports betting and media platform. You'll own critical infrastructure across compute, networking, storage, and cloud services (GCP/AWS) — driving complex migrations, building platform tooling and automation (ArgoCD, Helm, GitHub Actions), and improving observability and incident response across hundreds of production services spanning multiple regulated jurisdictions. We're looking for someone with strong Kubernetes and distributed systems experience, proficiency in Go, Python or Bash, and a track record of leading cross‑team infrastructure projects with high autonomy. You'll solve ambiguous problems, reduce operational toil through automation, mentor teammates, and bring a production‑first perspective to architecture decisions — all on a team that values pragmatic engineering, real ownership, and continuous improvement of how we work.

About the Work

• Drive complex infrastructure migrations and projects — scoping, planning, execution, and validation across multiple production environments and jurisdictions
• Build and maintain platform tooling and automation — ArgoCD, Helm, GitHub Actions, release pipelines, and service onboarding workflows that reduce toil for SRE and development teams
• Support development teams — consult on infrastructure needs, unblock cross‑team dependencies, review architecture proposals, and help teams adopt platform tooling and best practices
• Design and improve observability and alerting — Datadog monitors, dashboards, and runbooks that surface meaningful signals and make systems operable by the whole team
• Provide operational support and incident response — investigate and resolve production issues through structured debugging and root cause analysis, and contribute to on‑call rotations to maintain platform reliability

About You

• 5+ Years of Experience in a similar role (DevOps, Site Relatability Engineer)
• Strong experience operating and troubleshooting Kubernetes in a production Linux environment (cluster lifecycle, networking, storage, scheduling)
• Experience working with AWS, GCP, and/or on‑premise environments
• Proficiency in at least two of: Go, Python, Bash/Shell — for building tooling, automation, and debugging production systems
• Deep understanding of distributed systems — failure modes, networking fundamentals, capacity planning, and performance analysis
• Experience with GitOps and CI/CD workflows (ArgoCD, Helm, GitHub Actions, or similar)
• Experience with infrastructure-as-code (Terraform, Helm, or equivalent)
• Track record of leading complex migrations or infrastructure projects with cross‑team dependencies
• Strong incident response and troubleshooting skills — structured debugging across multiple services and infrastructure layers
• Clear technical communication — you write docs others can use, explain trade‑offs to varied audiences, and proactively unblock cross‑team dependencies

Nice to have

• Experience with service mesh technologies (Istio, Cilium)
• Familiarity with distributed storage systems (Ceph, or similar)
• Experience with bare‑metal Kubernetes or Talos OS
• Exposure to regulated environments (sports betting, fintech, or similar compliance‑heavy domains)
• Experience with Datadog or comparable observability platforms at scale
• Familiarity with database operations — PostgreSQL, connection pooling (PgBouncer), or database migration tooling

What We Offer

• Competitive compensation package.
• Comprehensive Benefits package.
• Fun, relaxed work environment.
• Education and conference reimbursements.

#LI-REMOTE

Salary Range

$145,000 — $193,000 CAD

Penn Interactive is proud to be an equal opportunity workplace. We will consider all qualified applicants for employment without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, disability, veteran status, genetic information, or any other basis protected by applicable law.Base pay is one part of the Total Rewards that Penn Interactive provides to compensate and recognize employees for their work. Most sales positions are eligible for a Commission under the terms of an applicable plan, while most non‑sales positions are eligible for a Bonus. Additionally, Penn Interactive provides best‑in‑class benefits to eligible employees. We believe that benefits should connect you to the support you need when it matters most, and should help you care for those who matter most. That’s why we provide an array of options, expert guidance and always‑on tools, that are personalized to meet the needs of your reality – to help support you physically, financially and emotionally through the big milestones and in your everyday life.