Vice President, Software Engineering & AI

Full time / Permanent / Sydney, Australia (Hybrid)

Job Description

VP of Engineering

Full-time | Hybrid | Sydney

The Company

Checkbox is a Series A Sequoia-backed technology start-up with a mission to enable meaningful work for all. To achieve this, we built a no-code automation platform with the belief that the power of digital creation needs to be accessible to everyone, not just IT teams. Seeing non-technical users surprisingly delighted when they use our technology to create in ways they never thought they ever could motivate us. Whilst our mission is big, our focus is sharp. Today we’re focused on in-house legal departments from companies including Disney, Elastic, J Frog, SAP and Coca-Cola.

Recently, we expanded our offering to not only help people do meaningful work, but manage it too. This came with the launch of our AI-powered Intake & Matter Management product – the “JIRA for lawyers”. This is part of our broader vision to be the “Legal Service Hub” for organizations, responsible for how legal work is raised, allocated, managed, and resolved. We believe that one day the Legal Service Hub will be as ubiquitous for legal teams as the CRM for commercial teams and we will win this category.

You’ll work alongside team members across the United States, Australia, and Asia, collaborating with incredible high performers and Co-Founders in the Forbes 30 Under 30 list. Our culture is one of our superpowers. It's what people talk about when they join us, work with us, and leave us. Read about what makes all of us a "Checkmate" here: https://www.checkbox.ai/core-values.

The Position

We’re looking for a VP of Engineering to be the technical leader at Checkbox, reporting to the founders & working closely with them to translate the product vision into a technical reality & plan. You will be joining Checkbox at a critical juncture in our growth journey with many challenges to overcome. We plan to double or triple our EPD team size over the next 1-2 years, while navigating rapidly evolving expectations around AI products & enabling technologies, paying down meaningful technical & product debt while continuing to innovate for our customers.

Working with the world’s largest enterprises means that we need to deal with substantial compliance, security & privacy considerations as well as a high degree of complexity in the product domains.

AI is a core part of our product strategy, and you will need to be able to navigate & adapt quickly as the landscape evolves while creating the right technical foundation for building robust, effective & innovative AI products. We also want AI to transform the way we operate as an organization as well, and you will champion & encourage the use of AI throughout the engineering organization.

About you

• 10+ years in engineering including senior leadership roles
• Scaled a Series A/B SaaS startup as a VP/Head of Engineering from around 20-30 engineers to 60-100 engineers
• You have experience building generative AI & data-enabled products
• You have specific, battle-tested opinions on team structure, process, and how to scale culture
• You've built or significantly evolved complex B2B/SaaS systems with enterprise-grade requirements
• Experience building or scaling distributed/remote engineering teams, ideally across time zones
• You understand modern infrastructure (cloud, containerization, CI/CD, observability) deeply enough to make good decisions
• You have war stories from managing technical debt and legacy system modernization—you've done this before
• You've made hard trade-offs between shipping fast and building for scale, know when to incur technical debt and when to pay it down
• You've successfully delivered complex initiatives with distributed teams and competing priorities

Why Checkbox?

We are an Australian start-up that’s recently expanded into the US as our next growth market, and have seen a spike in growth ever since. We’re backed by highly reputable VCs including Touring Capital, Peak XV (Previously Sequoia India) and Tidal VC. We’re passionate about building a culture where everyone feels supported and empowered to do their best work and grow professionally & personally. You will form some long-lasting friendships with smart, driven people for many years to come.

We also offer a whole host of benefits, including:
• Competitive salary & equity
• Hybrid working arrangements
• Personal learning & development budget
• Flexible leave policy
• Expense policy & salary sacrifices
• Start-up hub in the heart of the city
• Company wide social events
• Transparent & flat culture

Want to jump on board?

If you find this exciting and think you have what it takes, we would love to meet you. Please contact us at careers@checkbox.ai with your CV.

"Working at Checkbox has been an incredible journey of growth and discovery. Every day brings new challenges, fast learning, and the chance to work alongside a talented team that makes the experience both rewarding and enjoyable. "

– Monica Chan, Customer Success Manager

"Working at Checkbox has been one of the most rewarding experiences of my career. The culture here is built on trust, empathy, and genuine collaboration, where everyone’s ideas are valued, and we celebrate both growth and learning. We move fast, solve real problems, and support each other every step of the way. It’s a place where you can do your best work, be yourself, and feel part of something meaningful.”

– Yunliu Mok, Technical Lead

Learn About Our Values

At Checkbox, we’ve created an amazing and high performing culture for our people. Learn more about the values that define who we are.

See our values