What is it actually like to build Customer Success when nothing is clearly defined?

This is an honest look at why the Customer Success role often breaks down in early-stage companies.

Sam Brown (ex-Deel, ex-DataSnipper) has built and led Customer Success teams through rapid growth, messy data, unrealistic expectations, and constant pressure to scale before things are ready.

In this conversation, we unpack what actually causes Customer Success to fail and what operators can do differently.

We talk about:

• Why Customer Success is often set up to fail by mandate, ownership, and incentives

• How automating onboarding too early created more problems instead of leverage

• Why dashboards and health scores often hide real GTM issues

• The danger of building CRM processes before understanding what actually works

• Why customers needing Customer Success is often a product or GTM failure, not a win

This episode is for CS leaders and operators and founders who are trying to build user-first foundations.

In the Trenches is a podcast about how revenue actually gets built before playbooks exist.

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