Head of AI & Automation

UpGuard

22h • Remote

About The Position

UpGuard is seeking a Head of AI & Automation to lead A2, its central function for AI, workflow automation and analytics within the Operations department. The role leads a small team consisting of a Lead AI & Automation Analyst and two AI & Automation Engineers, and works closely with the AI & Automation Enablement Lead in the People team. The Head sets the organisation’s automation and AI strategy, determines what the team builds, and ensures that AI agents and automated business processes run on secure, reliable and well-governed platforms. The team enables departments to automate their own work with tools, standards and coaching, and directly delivers work that spans multiple teams or is too complex for a single team.

The role owns A2’s charter, operating model, rolling six-month strategy, quarterly OKRs, delivery process and technical direction. It oversees the roadmap for ug-buddy, UpGuard’s internal AI co-worker, and cross-functional automation delivery. It also establishes and audits production standards, partners with Cloud Platform Engineering and Security on hosting and incident response, conducts AI risk reviews in vendor procurement, and manages A2’s tooling and vendor relationships. The position serves as the central intake point for AI, automation and analytics requests and works with department heads to identify opportunities and communicate A2’s services.

Success is measured through delivery and reporting of quarterly OKRs, effort saved by automations, adoption of A2 tools, ownership of internal requests, production automation reliability, and employee understanding of A2’s services. The role’s approximate time allocation is 20% strategy and executive stakeholder management, 25% team leadership, 25% technical direction, 10% platform standards and governance, and 20% hands-on delivery of priority builds. The role works with senior leaders and departments across the company, technical and security teams, and external automation, AI and cloud vendors.

Requirements

• Bachelor’s degree in software engineering, computer science, cybersecurity or a related field.
• Several years of experience in cloud infrastructure, security and automation engineering, including production systems on Google Cloud.
• Working knowledge of large language models, AI agents, retrieval-augmented generation (RAG) and the Model Context Protocol (MCP).
• Experience with Infrastructure as Code (Terraform), containers, Kubernetes and Identity and Access Management.
• Experience leading and growing a technical team, setting strategy and OKRs, and reporting to executives.
• An automation and efficiency mindset, with a drive to safely and securely remove low-value, repetitive work across the company.
• Ability to manage several workstreams and stakeholder groups at once, keep people informed and resolve blockers.
• Strong written and verbal communication skills, including the ability to explain technical decisions, risks and trade-offs to executives and less technical colleagues.
• Comfort with UpGuard’s tenet of radical candour: honesty with respect and confidence to advance ideas diplomatically.

Nice To Haves

• Relevant cloud, security or AI certification, especially from Google Cloud.
• Experience in enterprise teams, particularly working with internal customers.
• Background in security operations or compliance, such as SOC 2, applied to AI and automation governance.

Responsibilities

• Set A2’s charter, operating model and rolling six-month strategy in alignment with the Chief Operating Officer and Steering Committee priorities.
• Define quarterly OKRs and report progress to the Steering Committee and Executive Committee.
• Select processes to automate and AI capabilities to build based on business impact, time saved and risk.
• Own the roadmap for ug-buddy, UpGuard’s internal AI co-worker.
• Lead, coach and performance-manage the A2 team; design team structure and roles; and recruit new members.
• Manage the team’s delivery process, including fortnightly sprints, prioritisation and a capacity model balancing project work, automation requests, team improvement and buffer.
• Set technical direction and architecture for AI agents, retrieval-augmented generation, MCP integrations and workflow automation.
• Review designs and production readiness for systems built on Google Cloud, including Vertex AI, BigQuery and GKE.
• Deliver cross-functional automations that are not owned by a single team, including processes such as employee offboarding across identity, collaboration and HR systems.
• Set production automation standards covering ownership, error alerting, enforced linting, documentation and least-privilege access; audit the platform and drive remediation.
• Work with Cloud Platform Engineering and Security on hosting, access control and incident response for A2 systems.
• Perform AI risk reviews in vendor procurement, assessing vendors’ AI use, data handling and contract terms.
• Own A2’s tooling and vendor relationships, including n8n, AI model providers and Google Cloud AI services.
• Act as the single point of contact for AI, automation and analytics requests through one intake channel, ensuring every request has an owner.
• Work with department heads to map processes and agree on what A2 will build or enable.
• Make A2’s services understood across the company through documentation, communication and training in partnership with the Enablement Lead.

Benefits

• Monthly lifestyle subsidy for financial, physical and mental well-being.
• Work-from-home setup allowance within the first three months.
• $1,500 USD annual Learning & Development allowance.
• Paid time off plus two additional UpGuardian leave days.
• 18 weeks of paid parental leave, irrespective of parenting role.
• Personal leave allowance, including sick and carer’s leave.
• Fully remote working environment; physical offices are available in Sydney and Hobart, with no compulsory attendance.
• Top-spec laptop provided for the role.
• Paid subscriptions to generative AI tools.

What This Job Offers

• Job Type: Full-time
• Career Level: Director