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A Journey in Outsourcing Support
When OutSchool 20x'd overnight during the pandemic, Sophie Heller scaled support from five people to over a hundred agents in weeks — largely through outsourcing.
with Sophie Heller, Former Director of Customer Experience at OutSchool
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49:41
Introduction
In March 2020, OutSchool’s user base multiplied by twenty in a single weekend, and the backlog hit fifteen thousand tickets within three weeks. Sophie Heller, the company’s first support hire, had to scale from a five-person generalist team to more than a hundred agents — while writing the documentation as she went.
She shares the unvarnished lessons: how to choose an outsourcing partner whose culture actually matches yours, why documentation is a non-negotiable prerequisite, the danger of long lock-in contracts, and why handing work over iteratively — one workflow at a time — beats a big-bang transfer every time.
What you will learn in this episode
When outsourcing makes sense — and when it quietly doesn’t
Why documentation must exist before the first outsourced ticket
Choosing a BPO on partnership and adaptability, not just price
Iterative handoffs: starting with one narrow workflow and earning trust
Running in-house and outsourced agents as one team with shared metrics
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