Article

Leading at Smartsheet: The fun is back

by Rhonda Keller

May 13, 2025

Rhonda Keller

 

In 1997, I began my career writing and delivering training for a software company and I’ve worked in customer education ever since. I’m sure you can imagine how much software training has changed in the last 30 years, but what you might not guess is how fun the industry used to be, how boring it became, and how lucky I am that, for me, it’s suddenly really fun again!

Of course teaching software was exciting in the beginning. I was in my early twenties, racking up frequent flyer points, and quite literally starting some of my classes with a quick intro to using a mouse. At the beginning of the dot-com bubble, the legacy solutions we were replacing were filing cabinets. Software was magic and instructors were wizards teaching our students to cast spells.

In the coming decades, as the industry matured and customers became tech-savvy, instructors evolved from wizards to tour guides. In the late ‘90s, customers used to leave our training with newfound superpowers. Software solutions were incredibly flexible, and we would teach students how to bend those solutions to turbocharge their processes. With the advent of SaaS and data-driven configuration over customization, tools became more and more rigid. Customers would leave our training with a list of processes they needed to bend to match our solution. Instructors were no longer teaching students how to create something, we were teaching them how not to break what was already created.

Through all of this, we were still teaching, equipping people with skills that make them successful, and that aspect, without question, has inherent rewards. Helping others succeed fuels most of us in customer success and is the reason I feel privileged to have had the chance to spend my entire career in this field … even when the subject matter was boring.

I assumed that’s how things would go for the rest of my career. I figured I’d lead programs that educate and certify customers on skills, but not superpowers, ever again. Until I got the amazing opportunity to lead Global Customer Education at Smartsheet—where the mission is real and every day we have the privilege of teaching professionals how to drive meaningful change in their organizations. Imagine being able to help a student (regardless of their industry, regardless of their processes) make their organization more collaborative and efficient. Students leave our classes with superpowers. The fun is back!

Want to see what I mean? Explore career opportunities at Smartsheet.