He left a $2B ARR company to build AI agents—then hit $1M ARR in < 6 months | Amit Shah, Founder of Instalily

A Product Market Fit Show | Startup Podcast for Founders

Amit walked away from being President of 1-800-Flowers after scaling it from $500M to $2B because he saw smart people trapped in dumb systems. His insight: half of global GDP is 90% manual work—salespeople entering data instead of selling, technicians reading manuals instead of fixing.

He started Instalily in Spring 2023 when everyone said AI agents were impossible. Instead of replacing workers, he built AI that finds signals in noise—telling each salesperson exactly which deal to focus on right now. The results are insane: $1M ARR within months, tripling revenue year two, delivering $150M+ value to single customers.

His secret? While competitors pitched flashy demos, Amit's team attended 100+ trade shows to understand actual operator pain. They hired fresh AI grads who "shipped fearlessly" instead of senior talent stuck in old paradigms.

Why You Should Listen:

• How "operator market fit" beats product market fit for enterprise sales
• The GTM playbook that hit $1M ARR in months by attending 100+ trade shows
• Why hiring AI-native grads crushed hiring senior talent for AI products
• How focusing on time-to-value unlocked enterprise deals
• The counterintuitive approach: augment the best parts of jobs, not the worst

Keywords:

startup podcast, startup podcast for founders, Instalily, Amit Shah, AI agents, enterprise sales, operator market fit, B2B SaaS, AI automation, vertical SaaS

00:00:00 Intro

00:04:42 Leaving 1-800-Flowers

00:09:55 Starting when everyone said AI agents were impossible

00:11:51 The vision—amplify the best parts of work, not replace the worst

00:16:59 Operator market fit over product market fit

00:20:48 Landing first $2B enterprise customers

00:29:00 The 100+ trade show GTM strategy that actually worked

00:33:02 Why they hired AI-native grads instead of senior talent

00:34:51 Hitting $1M ARR in months

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บท

1. Intro (00:00:00)

2. Leaving 1-800-Flowers (00:04:42)

3. Starting When Everyone Said AI Agents Were Impossible (00:09:56)

4. The Vision—Amplify the Best Parts of Work, Not Replace the Worst (00:11:53)

5. Operator Market Fit Over Product Market Fit (00:16:59)

6. Landing First $2B Enterprise Customers (00:20:48)

7. The 100+ Trade Show GTM Strategy that Actually Worked (00:28:59)

8. Why they Hired AI-Native Grads Instead of Senior Talent (00:33:02)

9. Hitting $1M ARR in Months (00:34:51)