The Last Mile

Associate Support Engineer

Full-Time in United States - Remote OK - $50k - $70k


The Engineering team manages and supports technical operations across The Last Mile organization, including internal tooling, and our Platform as a Service (PaaS) which operates in correctional facilities across the country. Daily engagements for an Associate Support Engineer range from triaging requests for support from remote facilities, to proactive monitoring of our PaaS infrastructure, and escalation of critical conditions. This is a highly collaborative role, with the opportunity to engage with an extremely broad range of systems and technologies.


The Associate Support Engineer is the first touch point for both our partners, and our internal users. This role is responsible for the content, and tone of communication with our audiences, and is pivotal in our ability to support our operations.

Our support desk operates a sprint based on-call rotation which allows our team members to cycle between being the owner for inbound events, and the first point of escalation and secondary responder as needed. The secondary responder period allows team members time to work on process or system improvements within support, and to engage in broader Engineering team projects as capacity allows.

This role is responsible for the triage and timely resolution of inbound events, as well as escalation of conditions which cannot be resolved directly. The support team collaboratively owns a considerable segment of the user experience across our audiences at The Last Mile.

Work with other members of the Engineering team to:

  • Provide first responder support to partners and team members via Slack, e-mail, and internal tickets
  • Prioritize efforts, support escalations, and drive resolutions in a timely manner
  • Monitor platform infrastructure, and respond to alerts
  • Manage internal and external communication for incident response, keeping stakeholders and partners informed

Required Skills and Experience:

  • A passion for problem solving in challenging conditions, and empowering people through technology
  • Strong verbal, and written communication skills
  • A fundamental understanding of computer hardware and peripherals
  • A fundamental understanding of IP services and protocols (Eg: DNS, HTTP(S), SSH)
  • A fundamental understanding of online security, and basic information security

Bonus Points for:

  • Experience using ticket driven workflows
  • A fundamental understanding of computer networking, including switching, routing, and the OSI model
  • Ability to understand and support processes written in Ansible, *sh, Python, or JavaScript
  • Familiarity with macOS, ChromeOS, or Linux environments
  • Google Workspace administration

Annual Salary: 50,000-70,000 adjusted based on experience and location

TLM is an equal opportunity employer. We value diversity and second chances at our organization. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other protected class.