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Episode Summary

Ilana Elbaz joined Deel when it was five people, one developer and no revenue. It is now 7,200 people across almost every timezone, with more than $1 billion in ARR — and it has never had an office. She built the go-to-market function that got it there, from Singapore, having grown up in France and started companies in Thailand, Switzerland and the US.

Deel went through Y Combinator in 2019 as something else entirely — first a social media product, then a blockchain company — before landing on the payroll, compliance and employment infrastructure it sells today. Much of that product exists because Deel needed it first: the employer-of-record product was built after contractors in Germany and Italy told the company they would not work as contractors.

In this episode of Pick My Brain, Alan Jones asks the question every Australian founder eventually hits: if the local market is small and the experienced talent is thin, when do you start hiring offshore? Ilana's answer is blunter than most — think global from day one, for the team and for the go-to-market, because the alternative is optimising for proximity instead of quality.

They also get into the compliance mistakes that can close a business, why an investor will interrogate your workforce structure at the next round, how Deel runs on written async communication and huddles instead of scheduled one-on-ones, and Ilana's case that the classic weekly one-on-one is obsolete once you have real-time data. Plus the SDRs who went from under $40,000 a year to more than $500,000, and why she would take that job again tomorrow.

Time Stamps

• 00:00 – Five people to 7,200, and zero to over a billion
• 00:58 – Welcome to Pick My Brain
• 01:45 – Meet Ilana Elbaz, head of sales and go-to-market at Deel
• 02:30 – Doctor or entrepreneur, and a first company at 19
• 05:02 – How Deel was founded, and the pivots through Y Combinator
• 07:26 – Is Y Combinator still worth applying for?
• 08:50 – Remote-first from day one, and why proximity is a bad filter
• 10:56 – Eating your own dog food: how the employer-of-record product got built
• 12:29 – Where 7,200 people actually sit
• 14:34 – Why a small market forces Australian founders outward
• 16:41 – Slack from day one: async, written and measured
• 18:07 – Akai by Deel and the daily performance report
• 19:58 – Think global from day one
• 21:08 – The compliance mistakes that can close your business
• 22:59 – Paying people in the currency they actually want
• 25:56 – Onboarding, buddies and enablement
• 26:33 – From under $40k to over $500k: the SDR path
• 27:56 – Bringing a distributed team together, and the Deel World Cup
• 30:24 – Why the classic one-on-one is obsolete
• 32:43 – Fix it now: the cost of postponing hard conversations
• 33:30 – Wrap-up

Resources

- Deel – https://www.deel.com/dayone

- Ilana Elbaz on LinkedIn – https://www.linkedin.com/in/ilanaelbaz

- Ask Alan a Question – https://speakpipe.com/pickmybrain

- More from Alan Jones – https://www.startupfoundercoach.com

Pick My Brain is a Day One show hosted by startup founder coach and investor Alan Jones.

Mentioned in this episode:

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