How I Got Here: Why Prefect CRO Hiro Rodriguez took the road less traveled

Before he became the chief revenue officer of DC orchestration startup Prefect, Hiro Rodriguez had a number of all-star tech gigs, including with names like Salesforce and DocuSign.

But before he jumped into the big leagues, Rodriguez had to figure out the path he wanted to follow.

He initially started college wanting to be a sports agent, but ultimately went for a political science degree with the intention of being a lawyer. By the time he graduated from the University of San Diego, though, he didn’t think law school was the right move for him. He spent a few years in Las Vegas, Nevada selling Cutco knives, which he said taught him a ton about sales, before landing a gig back in California and breaking into tech as an account executive for Salesforce.

Rodriguez told Technical.ly that he was drawn to the Bay area not only because he grew up there, but also because he was eager to jump into the tech world.

“I just really love the idea that technology can take 10 engineers or 15 different people, build a product and it becomes repeatable, and you can really have a positive impact on the way business is done,” Rodriguez said.

His next move was crucial in what would be his circular journey (more on that later). After a few years at Salesforce, Rodriguez had the chance to meet Keith Krach, the former chairman and CEO of DocuSign. He worked as the CEO’s chief of staff and director of executive engagement during his nearly four years at that company.

He did a brief stint at Prefect afterward, but that’s not what brought him to DC. After a few months with the startup, Krach again reached out to him with an offer to work as the chief business officer and senior advisor to the under secretary at the Department of State.

Rodriguez found the experience to be a strange but wonderful callback to his political science roots.

“I might have graduated with the degree in political science, but I had zero intention of using it once I decided I did not want to be a lawyer,” Rodriguez said. “But in this crazy world that we live in, I somehow ended up finding myself in DC.”

There, his initial task was to work on bridging the gap between Washington and Silicon Valley. When the pandemic hit, though, he was asked to help lead a task force to assist with personal protective equipment. With commercial planes grounded, State Department assets were needed to help get the equipment into the US.

Later on in 2020, though, Rodriguez headed back into the private sector for his current role at Prefect. Despite the two gigs’ big differences, he found a lot of his federal government agency experience could be applied to startups. He principally noted that a leader’s main job, no matter the company or organization size, is to set clear and honest directions.

“One of the things that I realized is that leadership principles are universal,” Rodriguez said. “So whether you’re at a startup with seven people or a big bureaucracy, the most important thing as the leader that we do is to set a crystal clear direction.”

Along the way, he’s also learned a lot about being a good employee and leader, including lessons like being humble and knowing when it’s okay to say that you don’t know and lean on a mentor or advisor. With all the twists and turns in his career, he has one large piece of advice for those wondering where the path will take them next.

“When opportunity comes, it’s important to jump in with both feet, water over your head, and just try,” Rodriguez said. “I would encourage other folks who are at a crossroads to say…that one might be the more unique or the interesting path, and just like Robert Frost said, take the road less traveled by. That would be my best advice to folks around it at a crossroad.”