Spotlight: Andrea Bumstead @ Kindsight

How did you get into customer success?

I began my career in marketing and then spent several years as an account executive. My transition into customer success was sparked by the industry’s shift toward subscription-based models and cloud-based solutions. I saw an opportunity to be at the forefront of a rapidly evolving industry and profession. Additionally, I’ve always had a passion for building relationships and working closely with customers, so moving into customer success felt like a natural and exciting fit for me.

What do most people get wrong about customer success?

A common misconception is that customer success doesn’t require sales skills. This couldn’t be further from the truth—upsells, cross-sells, and renewals are often integral to the role. In fact, customer success is a key revenue driver for most organizations. The ability to navigate commercial negotiations, identify opportunities to add value, and advise customers on new products or services is essential for any Customer Success Manager. These skills ensure both the customer and the business achieve their goals.

What advice would you give someone starting in customer success?

Start by connecting with Customer Success Managers to learn about their daily responsibilities, challenges, and rewards. Take a few courses, such as those offered by Success Hacker, and join customer success communities like the Customer Success Network, Women in Customer Success, or the CxXchange. Don’t worry about lacking direct experience in customer success—many successful professionals come from diverse backgrounds. As a leader, I’ve hired individuals with experience in fields like event planning, hospitality, fitness, and small business ownership. What truly matters is a customer-first mindset, strong problem-solving skills, and a genuine interest in helping others succeed. Having some sales skills also doesn't hurt ;)

What's the most rewarding part of your role as a VP of Customer Success?

The most fulfilling aspect of my role is working with people—both within my organization and with our customers. Internally, I thrive on collaborating with teams to solve complex challenges and refine go-to-market strategies. Externally, I love partnering with customers to understand their definition of success and designing journeys that deliver meaningful value. For me, the human element is both the most rewarding and the most challenging part of customer success, and it’s what keeps me deeply passionate about this profession.