Director of Observability

About the role

Kestra Holdings provides industry‑leading wealth management platforms for independent financial professionals. The company combines advanced business‑management technology with personalized consulting to deliver scale, efficiency, and support. The Director of Observability will build a brand‑new observability and reliability practice from the ground up, reporting to the Head of IT Infrastructure & Cybersecurity. The role starts with two direct reports—a Senior Observability Architect (India‑based) and a future US‑based Observability/Reliability Engineer—and will scale as the practice matures.

Responsibilities

• Define and execute the observability strategy aligned with business objectives, regulatory requirements, and the enterprise technology roadmap.
• Lead the hands‑on 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).
• Enforce 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.
• Operate the end‑to‑end incident management lifecycle: detection, response, escalation, communication, and blameless post‑incident review.
• Establish 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 phase, transitioning command to senior team members as the practice matures.
• Integrate incident workflows with Jira / Jira Service Management for ticketing, change correlation, and remediation tracking; partner with Cybersecurity to unify incident handling.
• Drive adoption of SRE principles: SLI/SLO definition, error‑budget policy, toil identification and automation, and operational readiness reviews.
• Establish reliability gates and embed reliability into the service lifecycle from design through production.
• Partner with Cloud & Platform Engineering, Cybersecurity, and application teams to ensure full instrumentation, measurability, and integration into SLO and incident frameworks.
• Align observability and incident management practices with NIST CSF 2.0 maturity targets and the firm’s cybersecurity roadmap.
• Support regulatory and audit requirements for a SEC‑regulated financial services firm (e.g., logging retention, evidentiary integrity, access controls on telemetry data).
• Lead and mentor the initial two‑person team, acting as a player‑coach who splits time between strategic leadership, hands‑on engineering, and direct mentorship.
• Develop a multi‑year workforce plan and talent pipeline to scale the team as the platform and service catalog grow.
• Foster a culture of blameless learning, operational excellence, and engineering‑led reliability across US and India coverage hours.
• 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 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.

Requirements

• 10+ years in observability, SRE, platform engineering, or infrastructure operations roles, with 3+ years in a people‑leadership capacity (Director or Sr. Manager level).
• Proven experience building an observability or SRE practice from scratch, including tool selection, instrumentation rollout, first SLOs, and incident command.
• Strong hands‑on technical depth; able to write code/IaC, configure platforms, build dashboards, and run incidents personally.
• 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.
• 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.
• Experience leading distributed teams across US and India time zones.
• Background 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.

Internal applicants must be in good standing, have a minimum of 1 year of service with Kestra, and at least 1 year in the current role unless approved by the EVP.

Benefits

• Competitive pay and benefits with a large employer (over 1,600 employees nationwide).
• 401(k) plan.
• Health insurance and a comprehensive benefits package.
• Supportive, collaborative environment committed to professional excellence.
• Opportunities to help clients navigate meaningful financial decisions.
• Training, development, and long‑term growth opportunities within the firm.
• Tuition reimbursement for qualified expenses.