Observability Engineer
Boston, MA | Full-Time | Client-Facing | Small Engineering Team (<10)
Overview
We are a rapidly growing cloud and observability-focused engineering organization delivering modern monitoring, reliability, and automation solutions for customers who expect speed, resiliency, and technical excellence. Our engineering culture is fast-moving, collaborative, and low-ego — and we hire individuals who are passionate about observability, curious about new technology, and comfortable working within a small, high-impact technical team.
If you thrive in environments where every engineer truly matters, this role offers a rare opportunity to influence architecture, standards, tooling, and culture from day one.
Position Summary
We are seeking 2–3 Observability Engineers to join our core technical team (currently under 10 engineers). In this highly technical and client-facing position, you will architect and implement observability frameworks across cloud-native and containerized environments, while working directly with customers to help them understand and improve system reliability, performance, and operational insights.
This role is ideal for someone who is hands-on, deeply curious, and proven through demonstrable work—code, talks, open-source involvement, technical writing, or prior observability tooling experience.
Key Responsibilities
Customer-Facing
- Engage directly with customers to understand operational challenges, goals, and desired outcomes.
- Translate ambiguous customer needs into clear, actionable observability solutions.
- Provide guidance, demos, and training on observability tooling, dashboards, SLOs, and best practices.
- Communicate effectively with both technical and non-technical stakeholders.
Engineering
- Architect and implement observability frameworks built on RED/Golden metrics, distributed tracing, structured logging, and automation.
- Build dashboards, SLOs, alerting systems, data pipelines, and instrumentation patterns that deliver actionable insights.
- Work with modern tools such as Datadog, OpenTelemetry, Prometheus, Grafana, Jaeger, Tempo, or similar platforms.
- Integrate observability into CI/CD pipelines and application code through proper instrumentation.
- Contribute to internal tooling and shared libraries that standardize observability across multiple services.
- Continuously explore new approaches, tools, and patterns to push observability forward.
What We Look For (Trust but Verify)
Because the team is small and the work is high-impact, we look for both technical capability and proof of curiosity and craftsmanship.
Evidence of Curiosity & Passion
Examples may include:
- An active GitHub/GitLab with contributions to open-source projects (e.g., OpenTelemetry collectors, instrumentation libraries, Kubernetes tools, Terraform modules, etc.).
- A personal website, blog, or technical writeups on topics such as:
- Distributed tracing
- Metrics design / SLO engineering
- Error budgets
- Kubernetes internals
- Observability pipelines
- Conference or meetup involvement:
- KubeCon, DevOpsDays, SREcon, re:Invent, or local Kubernetes/DevOps groups.
- Side projects, dashboards, tooling, or utilities created to solve real observability challenges.
Professional Presentation (Client-Facing Role)
- A polished resume without formatting issues or blank pages mid-document.
- A complete and professional LinkedIn profile with a photo (important for client-facing trust).
- Clear writing, attention to detail, and consistent technical communication.
Required Technical Skills
- Strong experience with Python, Go, or Bash
- Containers & Orchestration: Docker, Kubernetes
- Cloud Platforms: AWS, Azure, or GCP
- Observability Stack Experience (any combination):
- Datadog (preferred)
- OpenTelemetry (SDKs, Collector, instrumentation)
- Prometheus & Alertmanager
- Grafana, Jaeger, Kiali, Tempo, Mimir
- Familiarity with application instrumentation and the SDLC
- Configuration management: Ansible, Puppet, Chef, or Salt
- Understanding of logging standards, metrics pipelines, trace correlation, and distributed systems
Ideal Candidate Traits
- Highly curious, with a self-driven learning mentality.
- Comfortable operating in small teams with high ownership.
- Enjoys solving ambiguous, complex technical problems.
- Excellent communication and the ability to work directly with customers.
- Entrepreneurial mindset — comfortable shaping and evolving new systems and processes.
Compensation
- Base Salary: $110,000 – $140,000+
- Equity: Included
- Benefits: Full-time benefits, PTO, and strong growth potential.
Why This Role is Unique
- Direct impact on organizational observability strategy.
- Ability to shape internal tooling, standards, and best practices.
- Exposure to customers, frameworks, and environments across multiple industries.
- High visibility inside a fast-moving, technically sophisticated engineering team.
Job Disclaimer:
Equal Opportunity Employer/Veterans/Disabled
Benefit offerings include medical, dental, vision, term life insurance, short-term disability insurance, additional voluntary benefits, commuter benefits and 401K plan. Our program provides employees the flexibility to choose the type of coverage that meets their individual needs. Available paid leave may include Paid Sick Leave, where required by law; any other paid leave required by Federal, State or local law; and Holiday pay upon meeting eligibility criteria. Disclaimer: These benefit offerings do not apply to client-recruited jobs and jobs which are direct hire to a client
To read our Candidate Privacy Information Statement, which explains how we will use your information, please visit https://www.entegee.com/candidate-privacy-information-statement/
The Company will consider qualified applicants with arrest and conviction records.
#GRPA
Pay: $110,000.00 - $140,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Flexible schedule
- Health insurance
- Paid time off
- Vision insurance
Work Location: Remote
