Episode Summary

Ilana Elbaz was employee number five and the first go-to-market hire at Deel, helping scale the company from its early pivots through blockchain and payments to a business she helped grow from zero to hundreds of millions in ARR in just a few years. She's now an active angel investor and runs Deel's global pitch competition, which received tens of thousands of applications this year.

In this episode, Cheryl and Maxine unpack how operating inside one of the fastest-scaling companies in the world shapes the way Ilana evaluates founders as an investor. She breaks down her "3-star model" for backing companies (right infrastructure, right team, right timing, read from right to left), why she looks for founders with velocity and speed over founders who claim to have it all figured out, and why the biggest red flag at pre-seed is a founder who narrows their market too early.

You'll also hear why she pushes back on founders who insist on enterprise-only or single-market strategies before they even know their ICP, why treating international hiring as a growth problem rather than an HR problem is critical for founders building outside the US, and why Australian founders' instinct to think global from day one is a genuine advantage. Ilana shares what she learned scaling Deel's own go-to-market using the company's own product across dozens of countries, and why staying close to your first hundred customers matters more than shipping a polished product.

She closes with her Big Cojones moment: repeatedly landing alone in unfamiliar countries, from opening entities in Thailand to sourcing product in China at 19, with no support system and straight into meetings with lawyers she'd never met.

Time Stamps

00:00 - Intro

04:15 – Ilana's first investment: buying Amazon stock at age 10 and the lesson she learned selling too early

09:30 – Why Ilana joined Deel as employee five, drawn in by the labor law and compliance nightmare of scaling internationally

14:05 – The 3-star model: right infrastructure, right team, right timing, and why it should be read backwards

17:50 – Why founders who claim to have it all figured out should be a pass

21:40 – The danger of narrowing your market too early at pre-seed

28:10 – Why treating global hiring as a growth problem, not an HR problem, changes everything

33:00 – What makes Australian founders well suited to thinking global from day one

36:45 – How to answer "what's your expansion plan" as a green flag for investors

40:20 – Inside Deel's global pitch competition: 35,000 applications and five investments

46:10 – Big Cojones moment: landing alone in unfamiliar countries to open new markets

Mentioned in this episode:

Pear Tree

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Deel x PX_Script 2

Deel x PX_Script 1

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