Head of AI & Automation

Who are we?

At UpGuard, we are replacing manual security bottlenecks with AI-driven precision. Fresh off a US$75M Series C, we are scaling our infrastructure to process 100 billion risk signals daily. This isn’t just growth; it’s a total reimagining of how the world manages cyber risk.

We build the Cyber Risk Posture Management (CRPM) platform that security teams actually love. By integrating security ratings, threat intel, and agentic AI, we empower organisations to stay ahead of an ever evolving attack surface.

We aren’t just building another tool; we’re defining a category. We provide the autonomy to ship world-class technology and the resources to do it at a global scale.

UpGuard is seeking a Head of AI & Automation to lead A2, our central function for AI, workflow automation and analytics within the Operations department. You will lead a small team of a Lead AI & Automation Analyst and two AI & Automation Engineers, and work closely with the AI & Automation Enablement Lead in our People team.

You will set UpGuard's automation and AI strategy, decide what gets built, and make sure the AI agents and automated business processes the team delivers run on secure, reliable and well-governed platforms. Where a team can automate its own work, you give it the tools, standards and coaching to do so. Where the work spans several teams or is too complex for one team to build, your team delivers it directly.

What will you accomplish?

• Set A2's charter, operating model and rolling 6-month strategy, aligned with priorities from the Chief Operating Officer and the Steering Committee (SteerCo)

• Define quarterly OKRs for the function and report progress to SteerCo and the Executive Committee (ExCo)

• Decide which processes to automate and which AI capabilities to build, based on business impact, time saved and risk

• Own the roadmap for ug-buddy, UpGuard's internal AI co-worker, which connects company knowledge, data and tools through a single interface

• Lead, coach and performance-manage the A2 team, design its structure and roles, and recruit new team members

• Run the team's delivery process: fortnightly sprints, prioritisation, and a capacity model that balances project work, automation requests, team improvement and buffer

• Set the technical direction and architecture for AI agents, retrieval-augmented generation (RAG), MCP integrations and workflow automation

• Review designs and production readiness of the systems the team builds on Google Cloud (Vertex AI, BigQuery, GKE) and n8n

• Deliver cross-functional automations that no single team owns, such as employee offboarding across identity, collaboration and HR systems

• Set the standards every production automation must meet (ownership, error alerting, enforced linting, documentation and least-privilege access), audit the platform against them and drive remediation

• Work with Cloud Platform Engineering and Security on hosting, access control and incident response for A2 systems

• Perform the AI risk review in UpGuard's vendor procurement process, assessing each vendor's 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 where every request gets an owner

• Work with department heads to map how their processes run and agree on what A2 will build or enable

• Make A2's services understood across the company through documentation, communication and training, together with the Enablement Lead

How will success be measured?

• Quarterly OKRs delivered and reported to SteerCo

• Effort saved by shipped automations, in hours and dollars

• Adoption of A2 tools across the company, including the automation platform and the AI co-worker

• Every internal request has an owner, with none bounced

• Reliability of production automations: success rate, and failures caught by alerting rather than reported by users

• Share of the organisation that can say what A3 does and how to reach it (survey)

How is the time split?

• Strategy, planning and executive stakeholder management: ~20%

• Team leadership, coaching and recruitment: ~25%

• Technical direction, architecture and design review: ~25%

• Platform standards, AI governance and vendor management: ~10%

• Hands-on delivery of priority builds: ~20%

Who will you work with?

• Internal: the Chief Operating Officer, SteerCo and ExCo, department heads across Operations, People, Finance, Legal, Revenue and Product, Cloud Platform Engineering, IT and Security Operations, and the central Analytics team

• External: automation, AI and cloud vendors

What do we need from you?

• A 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, RAG and the Model Context Protocol (MCP)

• Experience with Infrastructure as Code (Terraform), containers and 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 - a drive to remove low-value, repetitive work across the company in a safe and secure way

• The ability to run several workstreams and stakeholder groups at once, keeping people informed and resolving blockers

• Strong written and verbal communication skills, with the ability to clearly explain technical decisions, risks and trade-offs - both to executives and to less technical colleagues

• Be comfortable with UpGuard's tenet of 'radical candour' - honesty with respect, and the confidence to advance your own ideas, diplomatically.

What would give you an edge?

• Any relevant cloud, security or AI certification, especially from Google Cloud

• Experience in enterprise teams, particularly with internal customers

• A background in security operations or compliance (e.g. SOC 2), applied to AI and automation governance

What’s in it for you?

• Monthly Lifestyle subsidy: Use this for financial, physical, and mental well-being

• WFH set-up allowance: To ensure you have the right environment to work in, we will help you get set up within your first 3 months at UpGuard

• $1500 USD annual Learning & Development allowance: To support your career development, all team members will be able to expense development opportunities against this allowance

• Annual leave: PTO plus two additional UpGuardian leave days to give you time to recharge your batteries.

• 18 weeks paid Parental Leave: Irrespective of parenting role

• Personal Leave Allowance: This includes sick & carer’s leave

• Fully remote working environment: While we have physical offices in Sydney & Hobart, we do not mandate compulsory attendance

• Top-spec hardware: All team members will be provided with top-spec laptops for their role

• Generative AI subsidy: UpGuard provides paid subscriptions for all team members to access generative AI tools to support their work.

UpGuard is a Certified Great Place to Work® in the US, Australia, UK and India, establishing its position as a leading global technology employer. 99% of team members agree that UpGuard is a great place to work! Apply now to find out why!

As an Equal Employment Opportunity and Affirmative Action Employer, qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, or disability status.

Please Note: Not all roles can be performed from the United States. Please check your specific job listing to confirm its advertised location. If the role you are applying for is listed as based in the US, we are currently only able to support hiring in the following locations: CA, CO, FL, IL, MA, MD, MO, OR, PA, TX, WA, and DC.

Before starting work with us, you will need to undertake a national police history check and reference checks.