Successfully Moving Upmarket

Part 3: Wonderschool 2020-2021

In my last 3 firms, I operationalised a move upmarket successfully, but all were very different scenarios.

In this, the final part of the series, I’ll break down what I found when I turned up at Wonderschool Inc, and how I successfully influenced the executive team and investors like Jeff Jordan at a16z, Josh Kopelman at First Round Capital and Andy Johns at Unusual Ventures that we should pivot the business from Marketplace to SaaS.

And most importantly, I’ll walk you through how we successfully executed that move and simultaneously moved upmarket!

Buckle up, this was a short but ultra-successful and action-packed journey, which recently saw Wonderschool raise a $25m series B!

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Wonderschool (March 2020 - April 2021)

Wonderschool is a Child Care Management System, that was originally designed as a 2-sided marketplace with a mission to help anyone start a school for kids aged 0-5 within their home.

Dubbed the Airbnb of child care Wonderschool is led by CEO Chris Bennett who had successfully pitched famed marketplace investor Jeff Jordan of a16z (eBay, OpenTable, Instacart etc) to lead a large series A.

Nothing is perfect in a startup, not even after securing a chunk of change from a16z, but very little could have prepared me for what was to follow… 🍿

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