AMA: Wyllo Sr. Director, Customer Success, Brett Milstein on Customer Success Leadership

How do you set realistic goals for customer success teams, and how often do you revisit and adjust these goals?

Are there specific books, courses, or resources you recommend for aspiring customer success leaders to enhance their skills?

How do you foster collaboration and communication between customer success, sales, marketing, and other departments within the organization?

How do you evaluate and adopt new customer success technologies to enhance the efficiency of your team?

What advice do you have for someone aspiring to become a successful customer success leader?

What's the best way to communicate a new SaaS platform tool/feature to your customers? EDM? Webinars? A combination or something else?

Ultimately we want to increase client engagement on our platform

What are the best tools to manage customer health and platform usage/adoption for a SaaS company with <200 customers but scaling quickly?

How do you build a case for CS being a revenue center, not a cost center, to the exec team and board?

What's the one metric you'd defend to the board if you could only pick one?

What's your approach to managing CSMs through a layoff or restructuring without destroying trust with customers?

How do you handle it when product ignores repeated customer feedback CS has escalated?

How aggressively do you push customers toward expansion versus protecting the relationship?