Director of Observability

Lead with Purpose. Partner with Impact.

We are seeking a Director of Observability to stand up a brand-new observability and reliability practice from the ground up at Kestra Holdings. This is a working leadership role — the Director will be expected to be hands-on in the early phase: selecting and configuring tooling, writing instrumentation standards, building the first dashboards and alerting pipelines, and personally running incident command for major events while the team and platform mature.

This is a newly created leadership role reporting directly to theHeadof IT Infrastructure & Cybersecurity. The Director will start with two direct reports — a to be hired Senior Observability Architect (India-based) and a future US-based Observability/Reliability Engineer — and will be expected to scale the team over time as the practice and service catalog grow.

What you’ll Do:

• Observability Strategy & Platform Hands-On Build-Out.


• Define and execute the observability strategy for Kestra Holdings, aligned with businessobjectives, regulatory requirements, and the enterprise technology roadmap.


• Personally lead theinitialbuild-out of the observability platform across metrics, logs, traces, profiles, and alerting — including tool evaluation, POCs, architecture, deployment, and configuration (e.g., Azure Monitor/Log Analytics, Datadog, Grafana,OpenTelemetry, Elastic/Splunk).


• Work withand enforceexistinginstrumentation standards (OpenTelemetry, structured logging, distributed tracing) across infrastructure and application teams.


• Build the first generation of dashboards, SLO scorecards, and a single pane of glass for Tier-1 service health — rolling up sleeves alongside the Sr. Architect and engineer.


• Operate the firm\'s end-to-end incident management lifecycle — detection, response, escalation, communication, and blameless post-incident review.


• Stand up on-call schedules, escalation policies, and runbook-driven triage for Sev1–Sev4 incidents via PagerDuty/xMatters or equivalent.


• Serve as primary incident commander for major incidents during theinitialbuild phase, transitioning command responsibilities to senior team members as the practice matures.


• Integrate the incident lifecycle with Jira / Jira Service Management (JSM) for ticketing, change correlation, and remediation tracking; partner with Cybersecurity so incidents run once, not separately by Infra and Cyber


• Facilitate post-incident reviews (PIRs), track remediation items in Jira, and report trends to leadership.


• Drive adoption of SRE principles across the firm: SLI/SLO definition, error budget policy and enforcement, toil identification and automation, and operational readiness reviews.


• Establish releaseofreliability gates and embed reliability into the service lifecycle from design through production.


• Partner with Cloud & Platform Engineering, Cybersecurity, and application teams to ensure all services are fully instrumented, measurable, and integrated into the firm\'s SLO and incident frameworks.


• Ensure observability and incident management practices align with NIST CSF 2.0 maturity targets and support the firm\'s cybersecurity roadmap.


• Partner with the Cybersecurity team to integrate observability data with Jira/JSM, CMDB, and SIEM for enriched context during incidents.


• Support regulatory and audit requirements appropriate for a SEC-regulated financial services firm (e.g., logging retention, evidentiary integrity, access controls on telemetry data).


• Directly lead and mentor a small, high-leverage team of two to start: a Senior Observability Architect (India-based) and a US-based Observability/Reliability Engineer.


• Operate as a player-coach — splitting time between strategic leadership, hands-on engineering, and direct mentorship of the senior architect.


• Build a multi-year workforce plan and talent pipeline to scale the team as the platform, service catalog, and 24/7 coverage needsgrow.


• Foster a culture of blameless learning, operational excellence, and engineering-led reliability across US and India hours of coverage.


• Serve as the primary technical liaison for observability and incident management vendors (e.g., Datadog, PagerDuty/xMatters, Grafana Labs, Elastic/Splunk, Atlassian).


• Represent Observability & Reliability in the Architecture Review Board, IT Change Management Board, and incident command forums.


• Provide regular reporting to SVP and executive leadership on reliability KPIs (MTTD, MTTA, MTTR, SLO compliance, alert signal-to-noise), incident trends, and strategic initiatives.

What You Bring:

• 10+ years in observability, SRE, platform engineering, or infrastructure operations roles, with 3+ years in apeopleleadership capacity (Director or Sr. Manager level).


• Demonstrated experience building an observability or SRE practice from scratch — toolselection, instrumentation rollout, first SLOs, and standing up incident command.


• Strong hands-on technical depths must be willing and able to write code/IaC, configure platforms, build dashboards, and run incidents personally, not just delegate.


• Deepexpertiseacross the observability stack: metrics (Prometheus, Datadog, Azure Monitor), log aggregation (Elastic/OpenSearch, Log Analytics, Splunk), distributed tracing (OpenTelemetry, Jaeger, Datadog APM), and profiling.


• Proven experience defining SLIs/SLOs, error budgets, and toil reduction programs.


• Hands-on experience with incident management platforms (PagerDuty,xMatters) and Jira / Jira Service Management integration for ticketing and workflow.


• Experience leading distributed teams across US and India time zones.


• Experienceoperatingin a regulated industry (financial services, healthcare, or similar) with familiarity with compliance frameworks (NIST CSF, SOC 2, SEC, FINRA).


• Excellent communication skills — able to present reliability posture, incident retrospectives, and risk to executive and board-level audiences.


• Experience withIaC(Terraform, Bicep, ARM), CI/CD pipelines, and embedding observability-as-code into modern DevOps practices.

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