Meet the Ripplers: Sarah Cannistra

Meet Sarah

Meet Sarah Cannistra, an avid fantasy fiction reader and a Bravo superfan with a personality as vibrant as her bookshelf. As Rippling’s Senior Manager, Learning Programs, Sarah helps employees ramp up and grow fast. Read below to see how she’s driving L&D in a culture defined by excellence and autonomy.

Ship From Day One

In simple terms, I make sure employees have the training and resources they need to grow their careers. More specifically, I design and run programs that get new hires and managers up to speed as quickly and confidently as possible. 

Rippling’s growth is insane, which means a lot of new faces, new roles, and new managers—about 55% of our managers have been promoted within the last six months to a year! So it’s my job to make sure people are ready to ship from day one. 

And when I say ship, I mean: “What are you shipping this week?” That kind of high performance is the baseline here. For example, when I joined Rippling, I had a proud mom moment where, within one week, I was able to get our first manager bootcamp program off the ground. 

I've accomplished more at Rippling in the best way possible in the eight months I've been here compared to the three and a half at my last role.

Top-Down Doesn’t Cut It

Rippling hires the ‘Avengers’—the best of the best. That means traditional top-down training doesn’t cut it. We’re peer-led with a self-serve culture, and that mindset shows up in everything I build. I like to say: I’m not the expert in everything, but I am the expert in helping you learn from the people who are.

We host live Manager-to-Manager roundtables, Manager Hacks, and monthly Learn the Business sessions. These are live conversations with people across functions and levels, and packed with insight. We supplement these with structured four-week cohort sessions for new managers, designed to build community and immerse them in what it means to join Rippling leadership.

Program Building Is World Building

At the moment, I'm excited about redesigning our onboarding process to create a more interactive 90-day learning journey. Now that I read fantasy instead of just business books, I’ve noticed my creativity has skyrocketed. It’s helping me reimagine onboarding as an immersive experience. 

When you jump into a book, you enter a whole new world. You need to understand the rules, the map, and the magic system. It’s all about the details. Whether I’m building a deck or designing a program, I now think in terms of storytelling rather than crossing things off a list.

Get Ready for Lift Off

Working at Rippling feels like the Olympics. It’s a team sport. You’re surrounded by world-class performers who genuinely love what they do and we’re all competitive in the best way possible. It can be intimidating, but if you’re here, it’s because you belong.

You have to believe in the value you bring and be proactive about your own development. We have so much autonomy, so much white space. No one’s going to strap you into the rocket ship for you—you’ve got to raise your hand, ask the hard questions, and go after the impact you want to make. 

That’s what I hope to instill and enable every day. Our team builds programs that reduce ramp time, but to me, we’re also investing in our people long-term and connecting with them as humans. 

I joke that I’m kind of like your favorite college professor and your older sister rolled into one. I guide people through their learning journey, but I also push them to think big and act fast.

This blog is based on information available to Rippling as of April 21, 2025.

Disclaimer: Rippling and its affiliates do not provide tax, accounting, or legal advice. This material has been prepared for informational purposes only, and is not intended to provide or be relied on for tax, accounting, or legal advice. You should consult your own tax, accounting, and legal advisors before engaging in any related activities or transactions.