Senior DevOps Specialist

Summary

Join Bugcrowd as a Senior DevOps Specialist and drive AI-first automation and Infrastructure as Code for our Operations Team. As part of the Advanced Services Group (ASG), you will build automation, tooling, and observability that power Strategy & Operations, including Delivery, Service Line Owners, and Customer Journey. You will reduce manual toil, raise delivery quality, and unlock data-driven insights by automating processes, building internal tooling, and using AI-driven workflow augmentation. Collaborate with operations teams, security specialists, and Customer Success to codify infrastructure, embed automation, and experiment with AI for workflow improvements. You will also design and maintain self-service dashboards, partner with data analysts, and develop automated QA checks. This role requires strong collaboration with various teams to enhance efficiency and delivery.

Requirements

• 5+ years in DevOps, SRE, or Platform Engineering roles
• Proficiency with Infrastructure as Code and CI/CD tools (Terraform, GitHub Actions, Argo, etc.)
• Strong scripting in Python, Go, or similar languages
• Exposure to offensive security, red teaming, or threat emulation practices
• Proven experience integrating or building AI/ML-powered tooling in ops or engineering contexts

Responsibilities

• Build and maintain IaC-based environments (Terraform, Pulumi) across AWS and multi-cloud targets
• Design automation for engagement orchestration—test environments, researcher provisioning, telemetry, triage
• Own CI/CD pipelines to deliver secure, auditable infrastructure for ephemeral offensive workloads
• Own CI/CD for internal tooling; ensure secure, auditable delivery of automation artefacts
• Partner with engineering to integrate automation logic into Bugcrowd’s core platform
• Integrate LLMs and AI agents into repeatable workflows (e.g., recon, scanning, triage, report drafting)
• Prototype and productionise bots that eliminate repetitive analyst tasks; iterate via prompt tuning and feedback loops
• Help define best practices for secure, transparent AI use in adversarial contexts
• Deliver automation modules that streamline Launch-Manager and CSM workflows—customer onboarding checklists, health-score dashboards, AI-generated QBR summaries
• Develop GTM enablement tools for service line owners — pricing/scoping calculators, ROI demo scripts, and live CRM integrations that surface upsell signals
• Design and maintain self-service dashboards with real-time alerts—tracking cycle-time, QA pass-rate, error budgets, margin and customer sentiment—so LoB GMs and CSMs can see service-line performance at a glance
• Partner with Data Analyst to surface actionable insights that drive continuous‑improvement sprints
• Develop automated QA checks to ensure consistency and compliance of engagement outputs
• Translate pentest and red team needs into codified logic and reusable automation
• Work closely with Product, Platform, and ASG Ops to drive end-to-end delivery efficiency
• Contribute to playbooks, observability frameworks, and SRE principles where applicable
• Work with service line Directors to prioritise GTM enablement backlog (pricing calculators, ROI demos)

Preferred Qualifications

• Experience with CRM/RevOps integrations (Salesforce, Gainsight) and automation tooling (Workato) a plus
• Bonus: Familiarity with tools like Caldera, BloodHound, Command and Control servers, redirectors, webservers, mailservers, Pwnboard, or other adversary platforms

Benefits

Remote, work-from-home 100% of the time