What are the biggest surprises when going from a company where customer success was established to one where you have to establish customer success?

My journey was the other way around. I started at a company where CS was brand new, and then came to a company where CS was established.

Looking back, here are some interesting findings.

• Perceptions of what Customer Success is/isn't vary widely, even if the function already exists at the company. When CS doesn't exist yet, there's an explicit need to educate the executives, sales reps, product org, etc. on what the team will do and the results they will drive. At a company where CS is established, that need for ongoing education still exists-- it just takes a different flavor over time.
• When there's no Customer Success (and even when there is), information on customers can be scattered all over the place. That's why we prioritized getting a CS tool early on, so if nothing else, we would have one place where customer documents, interactions, health, etc. were kept. It takes time to manage that change (put info here, not in your notepad) but it's worth it.
• If Customer Success hasn't existed, the company may be getting its first taste of churn (what prompted them to create Customer Success anyway?). That first taste of churn is bitter, and chances are the data and workflows around risk mitigation and learning from churn aren't well built out. This is an area to invest early- capture the reason codes, build a churn forecasting process, and educate everyone on churn and risk. Moves you make today may take 6+ months to have an impact so make sure to set expectations.

The most fundamental surprise is often how establishing CS requires comprehensive organizational change management—not just building a team, but reshaping company culture around customer outcomes. When transitioning from an established CS organization to building one from scratch, several surprising challenges often emerge:

1. Resistance to Customer Centricity

• Unexpected opposition: You'll be surprised by how many teams operate without considering customer outcomes

• Product-first mentality: Many organizations still build features first and consider customer success as an afterthought

• Sales disconnection: Finding that Sales sees their job as "done" at signature, with little consideration for post-sale success

2. Data Fragmentation & Visibility Issues

• Missing customer intelligence: Discovering critical customer data is scattered across spreadsheets, emails, and people's heads

• Incomplete journey tracking: Realizing nobody has mapped the full customer lifecycle or measured key transition points

• Usage blindness: Learning your product lacks basic instrumentation to understand how customers actually use it

3. Resource Struggles

• ROI skepticism: Having to repeatedly justify CS investments before you have established metrics

• Responsibility without authority: Being accountable for retention without control over product roadmap or support resources

• Expectation misalignment: Leadership expecting immediate impact while proper CS foundations take time to build

4. Cultural Transformation Challenges

• Breaking reactive patterns: Finding teams deeply entrenched in firefighting rather than prevention

• The "overhead" perception: Discovering CS is viewed as a cost center rather than a revenue driver

• Success ownership confusion: Unclear boundaries between CS, Support, Services, and Account Management

5. Customer Expectation Reset

• Relationship recalibration: Customers who have operated without CS suddenly expecting immediate transformation

• Trust rebuilding: Inheriting customer relationships that may have accumulated frustrations and unmet expectations

• Value articulation: Discovering customers don't understand how to measure their own success with your product