Sydney, New South Wales, Australia
๐ ๐๐ง๐ข @ ๐๐ถ๐ฟ๐๐ฎ๐๐ธ๐ฒ๐ฟ (๐๐ฆ๐ซ: ๐๐ฅ๐ง) โ ๐๐ฟ๐ถ๐๐ถ๐ป๐ด ๐๐ป๐๐ฒ๐ฟ๐ฝ๐ฟ๐ถ๐๐ฒ-๐ช๐ถ๐ฑ๐ฒ ๐๐ ๐ง๐ฟ๐ฎ๐ป๐๐ณ๐ผ๐ฟ๐บ๐ฎ๐๐ถ๐ผ๐ป I've spent 25+ years in technology starting as a software engineer, scaling through engineering leadership, and today serving as CTO at Airtasker, the local services marketplace that's a household name in Australia and scaling rapidly across the UK and US. ๐ ๐๐ถ๐ฟ๐๐ฎ๐๐ธ๐ฒ๐ฟ ๐ถ๐ ๐ฎ๐ ๐ฎ๐ป ๐ถ๐ป๐ณ๐น๐ฒ๐ฐ๐๐ถ๐ผ๐ป ๐ฝ๐ผ๐ถ๐ป๐. ๐ฆ๐บ AU: profitable, category-leading; GMV up 17.8% last quarter ๐ฌ๐ง UK: revenue +43.5%; GMV ARR at AUD 23M ๐บ๐ธ US: GMV +260%+ YoY as we build the playbook for a market many times our home's size โ๏ธ ๐ฆ๐ฐ๐ฎ๐น๐ถ๐ป๐ด ๐๐ฒ๐ฐ๐ต๐ป๐ผ๐น๐ผ๐ด๐ ๐ถ๐ ๐ต๐ฎ๐ฟ๐ฑ. It's the migration of legacy systems while traffic doubles underneath you. The 2am incident that tests a team's culture more than any offsite. The re-org that makes the next five years possible. I've lived all of it; at Atlassian scaling Jira from 3K to 50K users per license and leading 200+ engineers chasing 100M MAU; at Expedia running Flights services handling 150M+ searches a day; and now at Airtasker rebuilding the engineering, data and AI foundations of a multi-market marketplace. ๐งญ ๐ ๐ ๐น๐ฒ๐ฎ๐ฑ๐ฒ๐ฟ๐๐ต๐ถ๐ฝ ๐ฝ๐ต๐ถ๐น๐ผ๐๐ผ๐ฝ๐ต๐ ๐ถ๐ ๐๐ถ๐บ๐ฝ๐น๐ฒ: great technology organisations are built on ๐ฐ๐น๐ฎ๐ฟ๐ถ๐๐, ๐๐ฟ๐๐๐, ๐ฎ๐ป๐ฑ ๐ฐ๐ผ๐บ๐ฝ๐ผ๐๐ป๐ฑ๐ถ๐ป๐ด ๐ฑ๐ฒ๐ฐ๐ถ๐๐ถ๐ผ๐ป๐. Clarity about what matters to the business. Trust, so people move fast without waiting for permission. And a discipline for decisions that compound as this is where the real advantage lives. ๐ค ๐ง๐ต๐ฒ ๐ฏ๐ถ๐ด๐ด๐ฒ๐๐ ๐ฏ๐ฒ๐ ๐'๐บ ๐บ๐ฎ๐ธ๐ถ๐ป๐ด ๐ฟ๐ถ๐ด๐ต๐ ๐ป๐ผ๐ ๐ถ๐ ๐๐. I'm leading an enterprise-wide AI transformation at Airtasker, reshaping how we match tasks to taskers, how we serve customers, and how our teams operate. It's backed by the CEO and board. It's not a tech project; it's a business transformation powered by technology, and I own it end-to-end. ๐ฎ The next decade will be defined by companies that treat AI as the operating system, not a feature bolted onto the edges. ๐ง๐ต๐ฒ ๐๐ถ๐ป๐ป๐ฒ๐ฟ๐ ๐๐ถ๐น๐น ๐ฟ๐ฒ๐๐ถ๐ฟ๐ฒ ๐๐ต๐ฒ ๐ฐ๐ผ๐ฟ๐ฒ. ๐ฌ If you're a founder, CEO, or board member thinking about what that rewiring looks like for your business or a fellow exec or operator wrestling with the same questions, I'd love to connect. Open to CTO partnerships, advisory roles, and angel investing via Airtree Explorer.
The Airtree Explorer program exists to cultivate the next generation of angel investors in Australia and New Zealand. Through the program, Explorers get access to a world-class education on angel investing, become part of the best angel network in the region, and go on to back the next generation of Aussie and Kiwi startups.
At Atlassian Chaitanya led two vastly different organisations, first Jira Platform and then Growth. As the HoE for Jira Platform, he led the team (located in Sydney, Bengaluru and Poland) to increase scale and performance of Jira Software, which was and continues to be a company level OKR. Chaitanya, and his team, delivered initiatives that enabled the increase of user limits from 3000 to 50000 users per license. These included significant TTI improvements for key Jira views, launching the use of read-replicas for the largest customers, deploying customer instances to their closest shard etc. Atlassian then successfully migrating hundreds of large customers (like Splunk, Equifax, Paypal etc) from behind-the-firewall instances to the Atlassian Cloud. In his second role as HoE for Growth, he led engineering teams (with 200+ engineers) across the US, AU, and India. The primary mission was to grow MAU to 100M+. In this pivotal role, he led teams that owned and drove technology platforms and surfaces for www.atlassian.com, marketplace.atlassian.com, and in-product distribution surfaces that are the lifeblood of Atlassian's Flywheel business model. His responsibilities included steering the team through the development and execution of highly technical multi-quarter roadmaps, defining success measures, budgeting, and strategically allocating funding for incremental headcount. Overseeing execution, he ensured that engineering operations were meticulously optimised for reliability, stability, velocity, and developer productivity. Chaitanya was also the lead for the engineering promotion process. He drove several process improvements which helped it scale the process as the engineering organisation doubled in size during his tenure, while keeping the promotion bar high.
Expedia is one of the worldโs leading travel agents, with an extensive brand portfolio that includes some of the worldโs most trusted online travel brands. As such, engineering at Expedia is all about scale โ both in terms of people and in terms of volume of requests. The services managed and run, by Chaitanya's teams, enabled 150M+ searches, 200K+ bookings a day. At Expedia, he led a distributed engineering organisation of around 60, working on the Flights platform servicing the entire customer journey from search through to ticketing. Here he was responsible for software architecture & performance of the teamโs services exceeding SLAs for production support during incidents partnering with stakeholders across product, commercial strategy, and customer support performance management, recruiting and capacity planning managing multiple projects of varying complexity improving agile practices and processes coaching developers and managers planning the medium to long-term roadmaps
Hey You, at the time of his tenure, was Australiaโs largest mobile application for cafes, bars and restaurants aiming to create a connection between quick service restaurants and their customers. He led an engineering team of 15 across platform, web, iOS and Android. The team was distributed between Sydney and Manila. In 18 months, he doubled the size of the team, defined and implemented a scrum-based workflow across the entire company and built out cross-functional teams delivering value for consumers and merchants. He was responsible for all software engineering and infrastructure coordinating the product research and design process road map definition and ownership running offshore and onshore engineering teams managing multiple product streams across mobile, web and POS integration building a right sized engineering process for the business performance management, recruiting and capacity planning