The Official SaaStr Podcast: SaaS | Founders | Investors

The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr 478: How to Move Upmarket and Serve Multiple Customer Segments at the Same Time with Square's Global Head of Sales, Ashley Grech

Aug 27, 2021 · 24:40

Listen to Episode

✨ AI Summary

Square's Ashley Grech on moving upmarket and serving multiple segments.
Challenges and learnings from expanding offerings to larger businesses.
Strategies for serving diverse customer sizes simultaneously.

More from The Official SaaStr Podcast: SaaS | Founders | Investors

SaaStr 848: How AI Is Rewiring Sales: Quota, Retention & What's Actually Working with SaaStr, Salesforce and Mangomint

Apr 1, 2026 · 42:56

SaaStr 847: How MangoMint Increased Win Rates with an AI-Powered Stack

Mar 25, 2026 · 31:28

SaaStr 846: 10 Things to Know Before You Deploy Your First AI SDR with SaaStr's CEO and CAIO

Mar 18, 2026 · 01:05:48

SaaStr 845: How SaaStr Built a $5 million Pipeline Machine with 1.5 Humans and 20 AI Agents with SaaStr's Chief AI Officer and Momentum from Salesforce's VP of GTM

Mar 11, 2026 · 41:25

View all episodes →