11/06/2025

Lessons from Doozy: How Founder, Milo Hill, pivoted, listened to customers and scaled for success

We’re excited to announce that our podcast, Docue Digest, is back with a brand new series! This time, Ashleigh Evans, Senior Legal Counsel, sits down with founders to explore their startup journeys and uncover their top tips for scaling a business.

In the second episode of this series, we dive into the inspiring story of Doozy – the all-in-one employee experience platform keeping teams engaged, connected, and productive.

Milo Hill, the founder of Doozy, shares how he launched the business during the pandemic as a quiz app, before successfully pivoting into the B2B market. Throughout the conversation, Milo opens up about the key moments that shaped Doozy’s growth, including:

  • Overcoming early challenges and finding product-market fit

  • Pivoting from a consumer quiz app to a workplace engagement platform

  • Acquiring Doozy’s first customers and using feedback to shape the product

  • Lessons learned from bootstrapping and self-funding the business

  • Leveraging expert advice and embracing AI to enhance company culture

  • His advice for other founders: speak to your customers

Whether you’re at the early stages of building your startup or looking to scale, this episode is packed with actionable advice and real-world insights that every founder can learn from.

You can listen and watch the full video on our Youtube channel by clicking here.

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Ashleigh Evans

11/06/2025