Observability Deployment Lead — Cloud Migrations & Automation

groundcover; Boston (MA); Hybrid; USD 110,000 - 150,000; Full time

Job summary

groundcover is transforming how engineering teams understand and troubleshoot cloud-native applications. Our platform unifies infrastructure, application, and service visibility with eBPF-based deployment in the customer's own cloud.

We are growing our Customer Success team with a Deployment Engineer who blends hands-on engineering with practical project management to guide customers from planning to production.

Qualifications

• 4+ years in implementation or deployment engineering.
• Hands-on with Kubernetes, containers, and major cloud platforms.
• Experience with observability platforms and telemetry pipelines.
• Ability to write and troubleshoot scripts and use APIs.
• Strong project coordination and customer communication.
• Experience using AI tools in technical workflows.
• Experience migrating observability platforms or delivering production cloud-native rollouts.

Responsibilities

• Lead implementation and migration projects from kickoff through production readiness, customer acceptance, and handoff to the Technical Account Manager.
• Build practical project plans with clear scope, milestones, owners, and dependencies. Keep customers and internal teams aligned on progress, risks, and next steps.
• Work directly with customer engineering teams to deploy groundcover, configure integrations, and validate logs, metrics, and traces across their environments.
• Help customers migrate from platforms such as Datadog, Coralogix, New Relic, and Grafana’s open-source and commercial offerings, including dashboards, alerts, queries, and operational workflows.
• Use and improve migration tools, scripts, and reusable AI skills and workflows. Validate their outputs to increase delivery speed, accuracy, and repeatability.
• Coordinate migration testing and cutover plans, helping customers verify coverage and resolve gaps before completing the transition.
• Deliver practical enablement and document configurations, decisions, and remaining actions so customers and TAMs can build on a successful implementation.
• Partner with Solution Engineers, TAMs, Support, Product, and Engineering to remove blockers and turn recurring implementation challenges into product and tooling improvements.

Skills

Deployment engineering

Kubernetes

Cloud platforms (AWS/Azure/GCP)

Observability platforms

Automation scripting

Project coordination

AI tools in workflows

Customer communication

Tools

Datadog

Grafana

Prometheus

OpenTelemetry

Job description

groundcover is transforming how engineering teams understand and troubleshoot cloud-native applications. Our platform unifies infrastructure, application, and service visibility with eBPF-based deployment in the customer's own cloud.

We are growing our Customer Success team with a Deployment Engineer who blends hands-on engineering with practical project management to guide customers from planning to production.