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. Internal Application Policy: 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. Benefits to support you: - 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