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Roadie

Lead Site Reliability Engineer

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As a Site Reliability Engineer, you will ensure system reliability and performance, collaborate with various teams, and implement scalable infrastructure solutions.
Top Skills: ApmAWSAzureCi/CdGCPGitGitlabGrafanaPulumiTerraform

Roadie, a UPS company, is a leading logistics and delivery platform that helps businesses tackle the complexities of modern retail with unmatched delivery coverage, flexibility and visibility. Reaching 97% of U.S. households across more than 30,000 zip codes — from urban hubs to rural communities — Roadie provides seamless, scalable solutions that meet a variety of delivery needs. 

With a network of more than 310,000 independent drivers nationwide, Roadie offers flexible delivery solutions that make complex logistics challenges easy, including solutions for local same-day delivery, delivery of big and bulky items, ship-from-store and DC-to-door. 

Roadie is seeking a Lead Site Reliability Engineer to join our growing Technical Operations Team. We are looking for a leader with a proven track record of managing high-performing SRE teams in high-availability, mission-critical environments. The ideal candidate is a strategic problem solver with deep expertise in site reliability best practices, DevOps principles, AWS and GCP, Kubernetes, and automation. You will play a key role in driving reliability, scalability, and operational excellence across our platform.

What You'll Do

  • Lead and mentor teams focused on enhancing platform reliability, optimizing uptime, and improving software delivery, observability, and infrastructure operation
  • Architect, maintain, and optimize production and non-production Kubernetes clusters (EKS), as well as Elasticsearch (ES), MSK, RDS, and ElastiCache (Redis) clusters
  • Design, deploy, and manage monitoring and logging solutions using Prometheus, Loki, Thanos, Grafana, OpenTelemetry, and New Relic
  • Strategize and collaborate with cross-functional teams to proactively identify bottlenecks, optimize resource utilization, and prevent system failures
  • Define and enforce Service Level Objectives (SLOs), Service Level Indicators (SLIs), and error budgets to drive reliability improvements
  • Automate and streamline operational tasks, reducing toil and increasing efficiency across engineering teams
  • Plan and forecast service capacity and demand, optimize costs, and fine-tune system performance
  • Lead troubleshooting initiatives, post mortems, and resolve production and non-production incidents, ensuring high availability and performance
  • Participate in and manage a 24/7 on-call rotation, responding to incidents and driving post-mortem improvements
  • Willingness to work non-standard hours to facilitate production upgrades or deployments on occasion

Technology We're Using Now

  • Python, Ruby on Rails, Golang
  • React/Redux, Objective-C and Swift, Android
  • Postgres, Redshift, Redis, Kafka
  • AWS/GCP
  • Docker/Kubernetes
  • OpenTelemetry/Prometheus/Thanos/Loki/Grafana/New Relic/Sentry
  • Git/CircleCI
  • ArgoCD

What You Bring

  • 6+ Years in various SRE roles
  • 6+ Years in various DevOPS/System Engineering roles
  • 3+ Years in leading and managing SRE teams
  • 6+ Years of experience building and managing production Kubernetes infrastructure
  • 7+ Years experience with popular scripting languages (Python, Ruby, Bash, etc.)
  • Experience with Infrastructure as code such as Terraform or Crossplane
  • Experience with CI/CD Development tools (CircleCI, etc.)
  • Experience with GitOPS Tools (ArgoCD)
  • Experience using a broad range of AWS technologies (RDS, ElasticSearch, VPC, EKS, S3, CloudFront, MSK, Elasticache, CloudWatch, etc.)
  • Experience developing and maintaining YAML templating systems (Helm charts, Kustomize, etc)
  • Must be able to work independently, be self-motivated and handle multiple priorities
  • Comfortable working in a fast-paced agile environment

Finally, a willingness to admit what you don’t know, and learn what you need to learn quickly.

Why Roadie? 

  • Competitive compensation packages 
  • 100% covered health insurance premiums for yourself
  • 401k with company match
  • Tuition and student loan repayment assistance (that’s right - Roadie will contribute directly to your existing student loans!) 
  • Flexible work schedule with unlimited PTO 
  • Monthly 3-day weekends
  • Monthly WFH stipend 
  • Paid sabbatical leave- tenured team members are given time to rest, relax, and explore
  • The technology you need to get the job done

This role is not eligible for Visa sponsorship. Applicants must be authorized to work for any employer in the U.S.

What you need to know about the Boston Tech Scene

Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.

Key Facts About Boston Tech

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  • Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
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