Director of Observability

Kestra • Austin, TX

1d • Hybrid

About The Position

Kestra Holdings is seeking a Director of Observability to establish a new observability and reliability practice from the ground up. This is a hands-on leadership role where the Director will be responsible for selecting and configuring tools, defining instrumentation standards, building dashboards and alerting pipelines, and leading incident command during major events. The role reports to the Head of IT Infrastructure & Cybersecurity and will initially manage a team of two, with plans to scale the team over time. The Director will play a key role in defining and executing the observability strategy, ensuring alignment with business objectives, regulatory requirements, and the enterprise technology roadmap. This includes leading the build-out of the observability platform across various domains, enforcing instrumentation standards, and operating the firm's incident management lifecycle. The position also involves driving SRE principles, establishing reliability gates, and ensuring alignment with cybersecurity and regulatory frameworks. The Director will lead and mentor a distributed team, foster a culture of learning and operational excellence, and serve as a technical liaison for vendors. They will also represent Observability & Reliability in key governance forums and provide regular reporting to executive leadership.

Requirements

• 10+ years in observability, SRE, platform engineering, or infrastructure operations roles
• 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.

Nice To Haves

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

Responsibilities

• Define and execute the observability strategy for Kestra Holdings, aligned with business objectives, regulatory requirements, and the enterprise technology roadmap.
• Lead the initial build-out of the observability platform across metrics, logs, traces, profiles, and alerting, including tool evaluation, POCs, architecture, deployment, and configuration.
• 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.
• 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.
• Serve as primary incident commander for major incidents during the initial build phase.
• Integrate the incident lifecycle with Jira / Jira Service Management (JSM) for ticketing, change correlation, and remediation tracking.
• 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.
• 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.

Benefits

• Competitive pay and benefits with a large employer (over 1600 employees nationwide)
• 401(k), health insurance, and a competitive benefits package
• Work in a supportive, collaborative environment committed to professional excellence
• Help clients navigate meaningful financial decisions with confidence
• Opportunities for training, development, and long-term growth within the firm
• Tuition reimbursement for qualified expenses

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed