Episode SummaryIlana 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 Stamps00:00 - 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 First Cheque is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new First Cheque episodes and upcoming shows. Sponsors:First Cheque is supported by our wonderful sponsors:Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast. Visit https://www.deel.com/dayone ___ Pear Tree: Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman. As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs. The offshore horror stories you hear usually aren’t a talent problem. They’re the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach through a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business. As part of the Day One community, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at http://dayone.fm/peartree Brought to you by Pear Tree. Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman. As local hiring becomes more expensive and harder to fill, many operators are turning to offshore talent across engineering, development, marketing, accounting and operations at a fraction of local salary costs. The offshore horror stories you hear usually aren't a talent problem — they're the result of outsourcing agencies that overcharge clients while underpaying staff. Pear Tree takes a different approach: a direct, transparent model where your team is paid fairly, fully compliant, and focused entirely on your business. As part of the Day One community, you'll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Learn more at https://dayone.fm/peartree Brought to you by Deel. Founders scale faster on Deel — set up payroll in any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Learn more at https://deel.com/dayone Mentioned in this episode: Pear Tree If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost. Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business. As a Day One listener, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. Deel x PX_Script 2 Deel x PX_Script 1 Pear Tree If you're a founder or operator trying to scale, here's the reality — Australian hiring is getting harder, salaries are at record highs, and the talent you need is increasingly out of reach. The best operators are quietly building offshore teams of engineers, marketers, accountants and analysts at a fraction of the cost. Pear Tree does it differently. We headhunt highly skilled talent from the Philippines and South Africa with full transparency on where every dollar goes, so your team is paid fairly and fully focused on your business. As a Day One listener, you’ll receive a free team audit to identify where offshore talent could move the needle in your business, plus 20% off your first hire. This podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrp Spotify Ad Analytics - https://www.spotify.com/us/legal/ad-analytics-privacy-policy/
