Ep207 – Dean Swan (VP for APJ at Monday.com) on growing Monday.com zero to $100M+ in APJ

The Startup Playbook PodcastInsights and lessons from the world's best entrepreneurs and investors Twitter Facebook YouTube Instagram Ep207 – Dean Swan (VP for APJ at Monday.com) on growing Monday.com zero to $100M+ in APJ February 27, 2025 rohitbhargava Podcast My guest for Ep207 of The Startup Playbook Podcast was the Vice President and General Manager for Asia-Pacific & Japan at Monday.com, Dean Swan. Dean spent 11 years at Microsoft before becoming the Country Manager for Australia & New Zealand at Dropbox. He’s now the Vice President and General Manager of APJ at Monday.com. When Dean joined Monday.com as the first hire in the region, he set an audacious goal: to grow his part of the business to $100 million in 5 years – an ambitious target considering the entire company was valued at $120 million at the time. Fast forward to today, he’s grown the team to 140 people and is just $2 million shy of that $100 million target – months ahead of schedule. In 2021, Monday.com went public and now boasts a market cap of $15.97 billion. In this episode we covered a variety of topics including:  How to effectively expand into new markets and territories How to hire and attract the best talent How Dean grew the business from zero to $100M in the APJ region The steps he takes to perform at his best, which led to him losing 20kg+ And much more! Timestamps: 3:38 Dean’s background 5:19 Early career experiences as a chef 9:12 Transitioning into technology 11:02 Learnings from 11 years at Microsoft 16:04 How to build culture in a company 21:35 His experience expanding Dropbox and monday.com into other markets 30:58 His own entrepreneurial journey prior to Dropbox & monday.com 38:22 Balancing vision with daily focus 42:18 Why he left Dropbox to help build out monday.com in APJ, early challenges 46:23 How he looks for and attracts talent 52.47 His initial growth plans for monday.com 59:33 Thoughts on AI and how he’s using it personally and at monday.com 1:06:56 The catalyst that made him prioritise his health and lose 20kg Our partners: A big thank you to Greg Walsom help his help with this interview! Also a big shout out to our long-term partners for the show: Scendar  Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on.Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time.The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club – Details & Cohort #1 applications available here Dean’s Links: Dean on LinkedIn monday.com People mentioned: Bill Gates Steve Balmer Satya Nadella Roy Mann Eran Zinman Greg Walsom Adam Schwab David Shein Companies mentioned: Microsoft Dropbox Google Hum Technologies Amazon G2 Luxury Escapes Tourism Australia Canva OpenAI Feedback/connect/say hello: [email protected] @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here https://traffic.libsyn.com/secure/startupplaybook/Ep207_-_Dean_Swan.mp3Podcast: Play in new window | Download | EmbedSubscribe: RSS admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. 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