System Administrator

Olo | No Office Location

Date listed

9 months ago

Employment Type

Full time





Total Funding

$81.3 million

Glassdoor Rating

4/5 (13 reviews)

At Olo we develop an online food ordering platform used by many of the country’s largest restaurant chains, reaching millions of consumers. Chances are if you’ve ordered directly from a restaurant brand’s app or website, we’ve made that happen. Mobile ordering and payments is an exciting and active industry full of interesting players and yet still a relatively untapped market ripe for disruption. We’re quite up-front about the technical challenges our business faces. Running a platform with multiple white-labeled front-ends, that maintains real-time connections into thousands of restaurants’ POS systems, and coordinates complex transactions between these and other third parties (such as payment gateways and gift card providers) is not for the faint of heart!

You’ll be joining our Infrastructure Team, responsible for keeping Olo’s food ordering and delivery systems up and running reliably and securely.

Our DevOps-oriented team uses Infrastructure-as-Code with automation wherever possible. The system has many moving parts and frequent deployments.

Any engineer may work at Olo’s headquarters in New York City’s Financial District or remotely from anywhere in the U.S. In fact, more than half of our engineering team is remote!


  • Administering Windows Server roles such as IIS, Active Directory, WSUS, and DNS.
  • Building virtual infrastructure in cloud platforms such as AWS.
  • Patching operating systems like Windows Server and Linux.
  • Patching third party tools and security related vulnerabilities.
  • Configuring Load Balancers, VPCs, and Security Groups.
  • Troubleshooting network latency including analyzing packet captures.
  • Proactively monitoring all systems for uptime and security. Noticing trends before they become issues. Improving Monitoring infrastructure as needed.
  • Responding to PagerDuty alerts as part of an on-call rotation with another engineer.
  • Resolving or escalating production issues to development teams as needed.
  • Managing domain forests and replication.
  • Forecasting and optimizing capacity and AWS infrastructure costs.

Required Skills/Experience

  • At least 3 years experience administering a production level 24/7 web application.
  • Expert level Windows Server knowledge, including IIS, Active Directory, Windows Server Performance Monitor, and Windows Networking.
  • In-depth working experience with AWS services and APIs.
  • Comfortable in your scripting tool of choice - PowerShell, Python, Bash etc.
  • Working knowledge of DevOps, automation, and Infrastructure as Code.
  • At least mildly comfortable in a Linux environment.
  • Solid networking knowledge, capable of troubleshooting all types of network traffic issues.
  • A passion for uptime.


  • Experience with any of the following technologies: Ansible, CloudFormation, GitHub, SQL Server, Redis, ElasticSearch, SumoLogic, Datadog, Windows Server Failover Clustering, Consul, Docker, Terraform.
  • PCI compliance experience.

 About Olo

Olo is the on-demand interface for the restaurant industry, powering digital ordering and delivery for over 250 restaurant brands. Olo’s enterprise-grade software powers every stage of the digital restaurant transaction, from fully-branded user interfaces to the back-of-house order management features that keep the kitchen running smoothly. Orders from Olo are injected seamlessly into existing restaurant systems to help brands capture demand from on-demand channels such as branded website and apps, third-party marketplaces, social media channels, and personal assistant devices like the Amazon Echo. Olo is a pioneer in the industry, beginning with text message ordering on mobile feature phones in 2005. Today, millions of consumers use Olo to order ahead (SKIP THE LINE®) or get meals delivered from the restaurants they love. Customers include Applebee’s, Chili’s, Chipotle, Denny’s, Five Guys Burgers & Fries, Jamba Juice, Noodles & Company, Red Robin, Shake Shack, sweetgreen, Wingstop, and more.