Vice President of Software Engineering

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.

In This Position, You Will

• Own the technical vision and roadmap for the next 18–24 months, balancing innovation with pragmatic debt paydown

• Design, grow & scale the engineering org to align with product strategy while managing technical dependencies

• Own engineering delivery – ensure we ship what we commit to, when we commit to it and do so with a high bar for quality, velocity & reliability

• Establish engineering processes, technical standard & practices that create predictability without bureaucracy, high quality outputs & scale with the org as we grow

• Balance competing priorities from product, sales, customers, and technical debt

• Drive operational excellence: uptime, performance, security, and scalability of production systems

• Bring on world-class talent & foster an engineering culture that attracts and retains top talent across distributed teams (Australia, SEA)

• Be the voice of engineering to the board, leadership team, customers, prospects, and partners when needed, including discussions on engineering progress, technical strategy & organizational health

• Represent engineering in executive team discussions on strategy, resource allocation, and company direction

• Adopt & champion an AI-forward mindset & engineering culture

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

• Experience building generative AI & data-enabled products

• Specific, battle-tested opinions on team structure, process, and how to scale culture

• Experience building or significantly evolving complex B2B/SaaS systems with enterprise-grade requirements

• Experience building or scaling distributed/remote engineering teams, ideally across time zones

• Deep understanding of modern infrastructure (cloud, containerization, CI/CD, observability)

• Experience managing technical debt and legacy system modernization

• Strong judgment making trade-offs between speed and scalability

• Successful delivery of 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.

Benefits

• Competitive salary & equity – We believe in employee ownership and comfortable compensation for our employees so that they can be as happy and productive as possible without any reservations

• Hybrid working arrangements – We have an office in the city and the team comes in on Tuesdays for our weekly all-hands kick-off (and we’ll grab coffee and lunch together), and on Fridays where we celebrate our weeks effort and go out for dinner

• Personal learning & development budget – Continuous development and growth is one of our core value, and we believe in developing our own home-grown leaders

• Flexible leave policy – You can choose to work on weekends or public holidays and take equivalent days off at another time to maximise your time off

• Expense policy & salary sacrifices – You can expense small work-related items and salary sacrifice larger items within reason

• Start-up hub in the heart of the city – Enjoy our city office which is decked full of snacks, drinks, premium coffee and coffee machine, and of course, a ping pong table and beers

• Company wide social events – Enjoy amazing company coffee, lunches & Friday night hangs and annual off sites to fun & exciting locations like Australia, Bali & Korea

• Transparent & flat culture – Enjoy the benefits of an open culture where all questions and feedback are welcomed so we can be a better company day by day