Observability Consultant ( Assessment and Strategy)

Location: 100% Remote Contract Role

About the role

We are seeking a senior Observability Consultant to lead an assessment of an enterprise observability environment and provide strategic recommendations for future improvements. This is a consulting engagement focused on discovery, assessment, and roadmap development—not day-to-day administration or implementation.

The consultant will work closely with technology leadership and technical teams to evaluate the current observability landscape, identify opportunities for optimization, and deliver recommendations that improve operational visibility, reliability, and overall observability maturity.

Responsibilities

• Lead project kickoff and establish the project plan, milestones, and communication cadence.
• Facilitate discovery sessions and workshops with technology leadership and key stakeholders.
• Assess the organization's current observability strategy, processes, and tooling.
• Evaluate approximately 15 observability platforms across enterprise and managed service environments.
• Review how current tools support monitoring, alerting, dashboards, analytics, telemetry, and operational workflows.
• Identify duplicate functionality, integration gaps, underutilized platforms, and opportunities for consolidation.
• Evaluate existing observability investments, including business value and overall effectiveness.
• Review current SLOs, SLIs, KPIs, and operational metrics to identify improvement opportunities.
• Develop practical recommendations to improve reliability, visibility, and operational efficiency.
• Deliver executive-level documentation, including current-state assessments, findings, recommendations, and a prioritized roadmap.
• Present final recommendations to technical leadership and project stakeholders.

Requirements

• 10+ years of experience in Infrastructure, Platform Engineering, Site Reliability Engineering (SRE), Enterprise Monitoring, or Observability.
• Experience performing enterprise observability assessments or technology consulting engagements.
• Strong understanding of observability concepts, including:
  • Metrics
  • Logs
  • Distributed Tracing
  • Telemetry
  • SLOs / SLIs
  • KPIs
• Experience evaluating multiple enterprise monitoring and observability platforms.
• Ability to identify opportunities for tool rationalization, consolidation, and modernization.
• Experience leading technical discovery sessions, stakeholder interviews, and executive workshops.
• Strong communication, documentation, and presentation skills.

Skills

Preferred technical experience—candidates should have hands-on experience with several of the following technologies:

• Datadog
• Dynatrace
• Splunk Observability
• LogicMonitor
• SolarWinds
• ThousandEyes
• Azure Monitor
• Grafana
• Prometheus
• New Relic
• ControlUp
• Redgate

Qualifications

• Experience in financial services or other regulated industries.
• Experience developing observability strategies, maturity assessments, or technology roadmaps.
• Background in cloud platforms, particularly Microsoft Azure.
• Experience supporting large enterprise environments with multiple monitoring and observability solutions.

Ideal Candidate

We're looking for a consultant who has helped organizations evaluate and improve their observability strategy—not someone who has simply administered a monitoring tool. The ideal candidate knows how to assess complex environments, engage effectively with both technical teams and executive leadership, identify opportunities for improvement, and deliver clear, actionable recommendations that guide future technology decisions.