A Frightfully Good GTM Strategy | RevvedUp Weekly

Hi ,

As we celebrate Halloween, here’s a reminder: the real “spooky” scenario isn’t ghosts, it’s pursuing the wrong customer segment.

Every growing B2B company faces a critical question: Who should we really be selling to?

Startups, mid-market firms, or enterprise giants all look appealing, but company size affects everything: deal speed, sales costs, and long-term retention.

In our latest blog, we explore why company size is one of the most important (and often overlooked) levers in your GTM strategy. You’ll learn:

• The trade-offs between SMB, mid-market, and enterprise segments

• How company size impacts sales cycles, churn, and ROI

• How to align marketing, sales, and pricing with each segment

• How focusing on the right size can unlock faster deals, stronger retention, and scalable growth

Read the full blog: Why Company Size Matters in Your B2B Go-to-Market Strategy

P.S: We are excited to attend and sponsor B2B Marketing's Global ABM Conference. We’ll be at Stand 21 and would love to meet you for a coffee.

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Resources too good to miss!

In this episode, How Block Is Becoming the Most AI-Native Enterprise in the World ft. Dhanji R. Prasanna, the discussion dives deep into how Block (formerly Square) is redefining what it means to be a truly AI-driven organization. Prasanna, Block’s Chief Technology Officer, shares how a bold cultural shift — one sparked by a single “AI manifesto” to Jack Dorsey — transformed the company from a collection of fintech brands into a unified, tech-first enterprise where AI fuels every team.

From launching Goose, Block’s open-source AI agent that automates complex workflows and saves employees up to 10 hours a week, to rethinking organizational design around technology rather than business units, Prasanna unpacks what it takes to scale AI impact across 3,500 people. He also discusses the counterintuitive lessons learned from building products like Google Wave, Cash App, and now Goose — including why code quality alone doesn’t create success, and how human creativity still defines the ceiling for machine performance.

The episode offers a rare inside look at how AI is changing not just productivity, but company DNA — from engineering and design to culture and leadership.

If you want to see what it really looks like when a global enterprise becomes “AI-native,” this episode is essential listening for tech leaders, product builders, and anyone rethinking how humans and intelligent systems can build together.

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