The Mid-Market Squeeze

You're too expensive for SMBs. Too lightweight for enterprise. Welcome to the mid-market squeeze.

The Challenge

From Below

SMB tools adding features

PLG companies moving upmarket

"Good enough" at better prices

From Above

Enterprise vendors simplifying

Freemium as trojan horse

Professional services bundling

Who's Caught in the Middle

The Warning Signs

Losing to "almost as good" alternatives

Enterprise deals require more customization than you can offer

SMB deals aren't worth the sales motion

The Metrics

CAC increasing without deal size increasing

Win rate declining at both ends

Customers churning to competitors above and below

Escape Routes

Go Up

Add enterprise features

Build professional services

Invest in security/compliance

Go Down

Create self-serve motion

Build freemium tier

Reduce sales touch

Go Focused

Pick a vertical

Dominate a niche

Become irreplaceable

Go Platform

Build ecosystem

Enable partners

Create switching costs

Success Stories

Notion

Started mid-market

Built PLG motion (down)

Added enterprise features (up)

Webflow

Designer focus (niche)

PLG growth (down)

Enterprise features (up)

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