Lead DevOps

Jobtailor; Town of Florida (NY); On-site; USD 180,000 - 240,000; Full time

Job summary

Jobtailor seeks a senior platform engineer to design observability and self-remediation for air-gapped customer-run environments. You will own end-to-end enterprise deliverables, working with Kubernetes, Helm, and Terraform/IaC across on-prem and cloud variants.

Lead by doing—managing 3+ engineers or acting as a hands-on tech lead, with GovCloud/FedRAMP experience preferred and a focus on auditability, self-service, and scalable automation.

Qualifications

• Track record operating enterprise software in customer-owned / on-prem / air-gapped environments, or GovCloud/FedRAMP deployments.
• Hands-on Kubernetes, Helm, Terraform/IaC and Docker/Compose; managed Kubernetes (GKE/EKS/AKS) and on‑prem.
• Observability you can ship into restricted environments (Prometheus, Grafana, ELK/OpenSearch, Splunk) and self-remediation design.
• Own enterprise deliverables end-to-end with customer IT — RACI, SLAs, checkpoints, scope, and dates.
• Leadership: managed 3+ engineers or hands-on tech lead to build/run a small team.
• Security & operability as infrastructure; auditability and self-service.
• GovCloud / FedRAMP experience preferred; AWS GovCloud / Azure Government / GCP Assured Workloads.
• Aerospace/government/on-prem experience; air-gap or ITAR/EAR exposure.
• Self-service/platform-engineering philosophy; AI-native task management.
• Secrets management, backup/DR, upgrade/migration tooling for disconnected sites; Fargate/ECS.

Responsibilities

• Design and implement observability and self-remediation for air-gapped, customer-run environments.
• Ship diagnostics and remediation playbooks; define health checks and alert automation.
• Build Helm charts, Terraform/IaC for multiple deployment variants; manage on-prem and cloud.
• Lead by example; hands-on infra work 20‑50% and mentor engineers.
• Define RACI, SLAs, checkpoints with customer IT; ensure repeatable deployments including GovCloud.
• Drive AI tooling adoption within the team.

Skills

Kubernetes Management

Helm Chart Development

Terraform/IaC

Docker

Prometheus

Grafana

ELK/OpenSearch

Splunk

Secrets Management

Tools

GKE

EKS

AKS

Fargate

ECS

Job description

• Make it operable without us.


• Design the observability and self-remediation story for air-gapped, customer-run environments — shipped diagnostics, remediation playbooks, health checks, alert auto-classification.


• Go deep: auto-diagnose and auto-remediate, not just \"rerun the pipeline.\"


• Package it for any environment. Build the Helm charts, Compose stacks, and Terraform/IaC for Pelico's real deployment variants — on-prem single-VM, air-gapped Kubernetes, and private-cloud (GKE/GKS, EKS, AKS) — deployable by customer IT with clean runbooks.


• Deliver on the commitment. Turn an enterprise deliverable — \"ship a GKS Helm chart in a month, with three people\" — into a roadmap with weekly checkpoints, MVP scope, and a date you hit.


• Make it repeatable — and federal-ready. Turn bespoke deployments into repeatable tooling that gets current and committed customers live without heroics — and stand up Pelico's federal posture (GovCloud / FedRAMP, controls as code), now a co-primary track and the most probable near-term direction.


• Set the boundary. Sit with customer IT and security months ahead, agree the RACI and SLAs, and draw an unambiguous line between what's theirs and what's ours.


• Lead by doing. Stay hands‑on (you'll choose ~20–50% infra work), set the bar, grow your engineers, and bring AI tooling into the team the right way.

Requirements

• A track record operating enterprise software in environments you didn't fully control — customer-owned / on-prem / air-gapped — or equivalent depth standing up regulated / government‑cloud (GovCloud / FedRAMP) environments (deep experience in either counts; the other is a fast ramp).


• Deep, current hands‑on Kubernetes + Helm + Terraform/IaC and Docker/Compose; managed Kubernetes (GKE/EKS/AKS) and on‑prem/bare‑metal.


• Observability you can ship into places you can't reach — Prometheus/Grafana, ELK/OpenSearch, Splunk; designing diagnostics and remediation for customer self‑operation.


• A record of owning committed enterprise deliverables end‑to‑end with customer IT — RACI, SLAs, checkpoints, scope — and hitting the dates.


• Leading by example — you set the bar by doing; ideally you've managed ~3+ engineers, or you're an exceptional hands‑on tech lead ready to build and run a small team.


• Comfort treating security & operability as infrastructure — you've operated in regulated, customer‑owned, or on‑prem environments and design for auditability and self‑service.


• Nice to have: GovCloud and/or FedRAMP experience (strongly preferred / expected) — AWS GovCloud / Azure Government / GCP Assured Workloads, or having taken a system through FedRAMP (Moderate/High), IL, or CMMC authorization.


• Aerospace / defense / government / regulated on‑prem experience; air‑gap or ITAR/EAR exposure.


• A real self‑service / platform‑engineering philosophy (golden paths, self‑remediation).


• AI‑native ways of working — scoped tasks, heavy context, retained ownership.


• Secrets management, backup/DR, upgrade/migration tooling for disconnected sites; Fargate/ECS.

Core Competencies

Demonstrates expertise in designing and implementing observability and self‑remediation solutions for customer‑run environments, with a strong focus on Kubernetes, Helm, and Terraform/IaC. Proven ability to manage enterprise deliverables and lead engineering teams in regulated environments, ensuring compliance and operational excellence.

Highest‑signal resume keywords

• Kubernetes Management


• Helm Chart Development


• Terraform/IaC Proficiency


• GovCloud/FedRAMP Experience


• Observability Design

ATS Optimization Keywords

Hard Skills

• Kubernetes


• Helm


• Terraform


• Docker


• Prometheus


• Grafana


• ELK


• OpenSearch


• Splunk


• Secrets Management

Soft Skills

• Leadership


• Collaboration


• Problem‑Solving


• Communication


• Team Building

Industry Keywords

• GovCloud


• FedRAMP


• Aerospace


• Defense


• Regulated Environments

Tools & Technologies

• GKE


• EKS


• AKS


• Fargate


• ECS