Meet the Ripplers: How Rippling caught Jonathan’s eye when he was still a startup founder

Name: Jonathan Como

Role: Tech Lead for Rippling’s HR Products organization

Location: San Francisco

Rippler since: 2023 

Role + responsibilities 

I’m a tech lead for Rippling’s HR Products organization. This is one of three major product pillars at Rippling (the others are IT and Finance). Day-to-day, I help build our new scheduling product and work with our insurance teams to execute a migration from an old benefits provider to a new one.More broadly, I’m deeply involved with recruiting, interviewing, and mentorship programs to ensure we hire, retain, and grow the best talent at Rippling. I also spend a lot of my time thinking about and helping teams with operational excellence, which is critical as we continue to scale the company.

This Rippler’s journey 

I was a startup founder for three years prior to joining Rippling. My introduction to Rippling was by way of a potential acquisition through a trusted former colleague and current Sr. Director of Engineering at Rippling, Daniel (DRB) Buscagalia. The acquisition didn’t work out in the end, and we eventually shut down the company. But I was incredibly impressed with the people I had met and was interested in the problems Rippling was working on—and it was apparently mutual, so I decided to take a role on my own.

There were two key reasons that I joined:

1. The business model and the compound startup. As a former business owner, I know firsthand how important it is to have a set of tools that “just work” to run the company—any time spent wrestling tools to run the business is wasted time. Having a system that integrates everything with the employee record is just magical. It was pretty easy for me to see how a suite of products built on top of Rippling’s platform can scale to be a massive business.

2. The motto: “freeing smart people to work on hard problems.” It’s no secret that Rippling seeks out founders, but you absolutely don’t have to be a founder to succeed at Rippling! You do, however, need to be a self-starter, dig deeply into problems, and feel comfortable with a high degree of autonomy and accountability. We look for these traits in every person we hire, and it’s exciting to work alongside that type of person.

Since joining Rippling earlier this year, it’s been a trip! I often joke that six months in Rippling Standard Time is at least six years anywhere else.

Memorable Rippling moments

Some of my favorite moments so far have been:

• Our team offsite over the summer, where everyone on the team from California, New York, and Washington had a chance to meet in person

• Launching our Recruiting product and having everyone at the company change their LinkedIn title to “Recruiter” to promote the launch

• “Coffee chats” with leaders. I’ve never experienced such a transparent culture from the senior leadership down to the nuclear teams

• Working with amazing teammates and leaders, like Director of Engineering Sachith Gullapalli, VP of Engineering Rakesh Rajan, and Chief Technology Officer Albert Strasheim (and many, many others whose names would take up too much space!)

Work + life

We work hard, but we know when to rest and recharge. I got married last year and took a couple weeks off. To be honest, I was a little bit anxious about taking time off since I had joined so recently, but my manager immediately allayed my concern and actually encouraged me to take more time. I didn’t get a single urgent ping while I was out—and I came back from vacation raring to go. 10/10, would take time off again.

One of the hardest things to manage initially was working across so many time zones: West Coast, East Coast, Asia, and Europe. This was a challenge across the company, and there was a recent initiative to be much more structured about “work hours”—each person and team decides their own work hours that are synced to our calendars. Most importantly, it’s now generally understood by everyone at Rippling that it’s OK to say no to meetings outside of work hours! While the outcome may seem like a simple thing, it’s super important to me, because it shows that the leadership team prioritizes the way we work, as much as they prioritize what we work on.

When I’m not building Rippling…

I live in San Francisco with my wife and our dog, Lola. Most weekends, you can find us biking, hiking, or sailing in the area. Lately, I’ve been spending a lot of time exploring the bike trails in Marin.

Tips for future Ripplers

At Rippling, we have a handful of core values, but my favorite one is “go and see.” It means ask good questions; figure out why that thing that everyone says is not working, is not working; dig into the details; crack open the code of an unfamiliar module; look for those weak signals in dashboards and metrics.

Rippling values people who don’t settle for surface-level understanding, so if you can do those things, you’ll be successful here!