Senior DevOps Specialist
Job Summary
We’re hiring a Senior DevOps Specialist to drive AI-first automation and Infrastructure as Code for our Operations Team. As part of Bugcrowd’s Advanced Services Group (ASG), you will build the automation, tooling and observability that power every corner of Strategy & Operations - Delivery, Service Line Owners, and Customer Journey. Your remit spans process automation, bespoke internal tooling, AI‑driven workflow augmentation and quality‑assurance frameworks. From scoping and triage through reporting, CS, and GTM enablement, you reduce manual toil, raise delivery quality and unlock data‑driven insight.
You’ll work alongside operations teams, offensive security specialists and a Customer Success function to codify infrastructure, embed automation into the engagement lifecycle, and experiment with AI agents and LLMs for intelligent workflow augmentation.
Duties & Responsibilities
Infrastructure & Automation
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
AI/ML & Workflow Acceleration
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.
Quality, Observability & Delivery Excellence
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.
Cross-functional Impact
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).
Education, Experience, Skills, & Abilities
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
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
Working Conditions
The ideal candidate must be able to complete all physical requirements of the job with or without reasonable accommodation.
Sitting and/or standing - Must be able to remain in a stationary position 50% of the time
Carrying and /or lifting - Must be able to carry / move laptop as needed throughout the work day.
Environment - remote, work-from-home 100% of the time.
ADA Statement
Bugcrowd is committed to the full inclusion of all qualified individuals. In keeping with our commitment, Bugcrowd will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact HR at ada@bugcrowd.com.
Senior DevOps Specialist
Job Summary
We’re hiring a Senior DevOps Specialist to drive AI-first automation and Infrastructure as Code for our Operations Team. As part of Bugcrowd’s Advanced Services Group (ASG), you will build the automation, tooling and observability that power every corner of Strategy & Operations - Delivery, Service Line Owners, and Customer Journey. Your remit spans process automation, bespoke internal tooling, AI‑driven workflow augmentation and quality‑assurance frameworks. From scoping and triage through reporting, CS, and GTM enablement, you reduce manual toil, raise delivery quality and unlock data‑driven insight.
You’ll work alongside operations teams, offensive security specialists and a Customer Success function to codify infrastructure, embed automation into the engagement lifecycle, and experiment with AI agents and LLMs for intelligent workflow augmentation.
Duties & Responsibilities
Infrastructure & Automation
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
AI/ML & Workflow Acceleration
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.
Quality, Observability & Delivery Excellence
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.
Cross-functional Impact
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).
Education, Experience, Skills, & Abilities
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
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
Working Conditions
The ideal candidate must be able to complete all physical requirements of the job with or without reasonable accommodation.
Sitting and/or standing - Must be able to remain in a stationary position 50% of the time
Carrying and /or lifting - Must be able to carry / move laptop as needed throughout the work day.
Environment - remote, work-from-home 100% of the time.
ADA Statement
Bugcrowd is committed to the full inclusion of all qualified individuals. In keeping with our commitment, Bugcrowd will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact HR at ada@bugcrowd.com.