Remote AI & Automation Strategy Leader

Matchbox; Melbourne; Hybrid; AUD 180,000 - 260,000; Full time

Benefits offered by this job

Monthly Lifestyle subsidy

WFH set-up allowance

Learning & Development allowance

Annual leave + extra days

Parental Leave (18 weeks)

Personal Leave Allowance

Fully remote work environment

Top-spec hardware

Generative AI subsidy

Job summary

UpGuard seeks a Head of AI, Automation & Analytics to lead A3, our central AI, workflow automation and analytics function within Operations. You’ll guide strategy, set OKRs, and deliver secure, scalable automations across teams, including ug-buddy and enterprise AI tooling.

You will manage a small team, collaborate with Security, IT and Product, and shape architecture for AI agents and RAG-enabled workflows. The role blends strategic leadership with hands-on delivery.

Qualifications

• Bachelor’s degree in software engineering, computer science, cybersecurity or 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, RAG and the Model Context Protocol (MCP).
• Experience with Infrastructure as Code (Terraform), containers and Kubernetes, and Identity and Access Management (IAM).
• Experience leading and growing a technical team, setting strategy and OKRs, and reporting to executives.
• An automation and efficiency mindset – a drive to remove low-value, repetitive work across the company in a safe and secure way.

Responsibilities

• Set A3's charter, operating model and rolling 6‑month strategy, aligned with COO priorities.
• Define quarterly OKRs for the function and report progress to SteerCo and ExCo.
• Decide which processes to automate and which AI capabilities to build based on impact, time saved and risk.
• Own the roadmap for ug-buddy, UpGuard's internal AI co-worker connecting knowledge, data and tools.
• Lead, coach and performance-manage the A3 team, design its structure and roles, and recruit new members.
• Run the team's delivery process: sprints, prioritisation and capacity balancing.
• Set technical direction and architecture for AI agents, RAG, MCP integrations and workflow automation.
• Review designs and production readiness of systems on Google Cloud and n8n.
• Deliver cross-functional automations across departments.
• Set production standards: ownership, alerting, linting, docs and least-privilege access; audit platform accordingly.
• Collaborate with Cloud Platform Engineering and Security on hosting, access control and incident response.
• Perform AI risk review in vendor procurement, assessing AI use and terms.
• Own A3 tooling and vendor relationships including n8n, AI providers and Google Cloud AI services.
• Be the single intake point for AI, automation and analytics requests.
• Map processes with department heads and define what A3 will build or enable.
• Promote A3 through documentation and training with Enablement Lead.

Skills

Cloud infra

Security

Automation engineering

Large language models

AI agents

RAG

MCP

Terraform

Kubernetes

IAM

Leadership

Education

Bachelor's degree in software engineering, computer science, cybersecurity or related field

Tools

Google Cloud

Vertex AI

BigQuery

GKE

n8n

Job description

UpGuard seeks a Head of AI, Automation & Analytics to lead A3, our central AI, workflow automation and analytics function within Operations. You’ll guide strategy, set OKRs, and deliver secure, scalable automations across teams, including ug-buddy and enterprise AI tooling.

You will manage a small team, collaborate with Security, IT and Product, and shape architecture for AI agents and RAG-enabled workflows. The role blends strategic leadership with hands-on delivery.