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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.
As a company, we are a young and tight-knit team of about 50 people across the United States, Australia, and Asia, made up of 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
At Checkbox you will be joining a small tight-knit team of passionate, intelligent & driven people. It is vital for us that our people feel a sense of individual impact, trust, and continuous growth while solving challenging problems to get things done. Our product team members are the innovators in our business, paving the way for growth opportunities and driving outcomes across our teams, and we’re always seeking smart, creative & driven people to join our team to build a world-leading product. You will be working with team members primarily based out of Australia & SEA.
Our design challenges are complex: Chief legal officers want visibility into the work attorneys do, but legal requests come in from all sorts of different channels ranging from Slack, email, intranet, Salesforce, JIRA, etc… Legal teams also need the ability to effectively triage work to the right teams and/or individuals, but solving this for teams of 10 looks significantly different to solving this for teams of 100. Attorneys also spend so much time on low value, repetitive work like reviewing standard contracts, asking for more information to provide legal judgements, and looking up historical cases & documents. How can we help them with this & allow them to focus on more strategic, high value work?
You will work to refine & shape the product vision & direction, lead product discovery, conduct user research, drive UX and UI work to design a first-class AI powered legal service management platform.
Key Responsibilities
In this position, you will:
+ Design world-class experiences for attorneys & legal admins to manage how legal work comes into the legal department & how it is fulfilled from start to finish.
+ Get close to customers, understand how they actually perform their workflows, learn about the legal domain & translate those insights into design priorities that drive user & business outcomes.
+ Design capabilities & systems that scale across multiple products & use cases, creating coherent end to end customer experiencesx
+ Practice & advocate continuous discovery & user research
+ Develop mockups, prototypes, user flows & any other assets required to deliver an AI first, cutting edge UI/UX & communicate complex concepts & interactions clearly to stakeholders
+ Work cross-functionally with Product, Engineering, and go-to-market partner to plan, design, build, and ship new capabilities that push the limits of possible
+ Develop & maintain the product design system & champion design principles
+ Advocate & champion the use of AI throughout the product development process
About you
+ At least 6 years of product design experience with a track record of shipping complex, high-impact products end to end from planning to QA
+ Proven ability to transform complexity into elegant simplicity with great taste
+ Strong craft skills & demonstrated attention to detail
+ Relentless customer & user focus. You dig deep to understand problems, motivations & come up with solutions from first principles
+ Experience designing complex enterprise software such as workflow, no-code or CRM platforms
+ Experience in a fast growing 0-1 and/or 1-10 scale startup
+ Developed & maintained design systems from scratch
+ Ideally have some experience with front-end development
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 – 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.
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.