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 the Head of 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 business objectives, regulatory requirements, and the enterprise technology roadmap. 
• Personally lead the initial build-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 with and enforce existing instrumentation 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 the initial build 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 release of reliability 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 needs grow.
• 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 a people leadership capacity (Director or Sr. Manager level). 
• Demonstrated experience building an observability or SRE practice from scratch — tool selection, 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. 
• Deep expertise across 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. 
• Experience operating in 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 with IaC (Terraform, Bicep, ARM), CI/CD pipelines, and embedding observability-as-code into modern DevOps practices.