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

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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:

• Rohit@startupplaybook.co
• @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