Heather Hiles






UC Berkeley - B.A. Economics

Yale - M.B.A.

Traditional, text-based resumes and portfolios can fall short when you’re trying to get a prospective employer or school admission counselor to pick you out of a pile. You can tell them about your achievements, but with such limited space, how do you show them? Enter Pathbrite and its CEO and Founder Heather Hiles.

With Pathbrite, students can, as Heather says, “collect, analyze, publish and share all evidence of their learning and achievement.” The digital platform lets users create visual portfolios, pulling in representative pieces of themselves — pictures, LinkedIn recommendations, personal websites, published work and more — into one spot.

For Heather, Pathbrite is the latest endeavor in a career that’s focused on closing the education and employment achievement gaps. A UC Berkley and Yale University grad, she has founded and led several private and public sector organizations, including an NGO to place women from welfare into careers.

In some ways, I’ll always be setting new goals for myself and whispering, 'Not quite yet.'

What inspired you to start Pathbrite? How do you intend people will use the site in their everyday lives?

My whole career before Pathbrite was focused on addressing gaps in opportunity, gaps in education and gaps in achievement.

For instance, back in the late 90s, I was CEO of a big welfare-to-work program for low-income women. We provided practical career education to 5,000 women living on welfare and then placed them in jobs paying salaries that would support them and their families. Later, when I served as a commissioner on the San Francisco Unified School District board, I saw firsthand the pernicious effects of income and opportunity disparities for kids who happen to have been born on the wrong side of the tracks. But the work I was doing just didn’t have the scale to make widespread, lasting and meaningful impact.

Pathbrite solves that problem. Pathbrite enables students and learners of all ages to collect, analyze, publish and share
all the evidence of their learning and achievement. Students use Pathbrite portfolios to help them get into the schools of their dreams or to land the perfect internship or launch a career. Evaluators, including admissions officers, instructors, recruiters and employers, use Pathbrite portfolios as an alternative to bubble tests, traditional résumés or other evaluation tools that fall short of illustrating the full capabilities of a whole human being.

Over time, we intend to take the aggregate data we collect to form a Knowledge Graph that will enable individuals or institutions to set goals and benchmark their progress against peers who share the same objectives. We'll also map an individual’s present education and achievements to their stated goals to illuminate pathways that can get them to where they want to go in life.

What does your job involve, and what types of responsibilities do you have in your position?

As an early-stage company, I spend a lot of time on deals. From financing to partnerships to sales, I’m externally focused much of the time. This is possible because I have the best team imaginable working on our product and driving our sales and marketing efforts.

What is your favorite part of your job?

I’m a natural people-person, so it really delights me that I get to be out in the world talking to people about things I’m passionate about: Pathbrite, obviously, but also education reform, closing achievement gaps and the future of work.

What challenges keep you awake at night?

We recently closed a series A round (the first significant round of venture funding). Finalizing that financing event really kept me awake at night, I tell you! Let’s just say I’m sleeping better now that it’s done. For how long? Who knows! But right now I’m sleeping better.

Is work/life balance ever a problem with you? If so, what is one no-fail tactic you use to create balance?

Of course. It’s always a struggle. My advice? Marry someone you really, really love. It’s working really well for me!

Was there ever a moment in your career where you’ve thought, “I made it!” What was it?

Definitely. I’ve said that many times. When I got into Berkeley and then Yale – both times I thought, “Wow, I’ve really made it.” When I became CEO of SFWorks, again, I thought I’d made it. And there have been several other times when I’ve thought this. But guess what? You start setting new goals for yourself and “I’ve made it” quickly becomes “not quite yet.” And I’m beginning to think it will be that way for me for the rest of my life. Maybe not all in the realm of career, but in some ways, I’ll always be setting new goals for myself and whispering, “Not quite yet.”

What are some of the rules you live by?

Respect and honesty are two sides of a coin I always carry with me. Transparency and communication are two sides of another coin I carry. There are others, but those are key.

What qualities does it take for someone to be successful in your line of work?

First, you’ve got to be both confident and intellectually curious. Fearlessness is another important quality. I find it’s helpful to keep asking a question until someone gives you an answer that makes sense to you. So, tenacity. More than anything, you really must have the strength of your convictions. In Silicon Valley, you can hear a lot of “no” before finally getting to a “yes” and that's hard.

What one piece of advice do you wish you could tell a 21-year-old version of yourself?

Trust your instincts. Listen to smart people, take in great advice, follow sage guidance, but always trust your instincts.

Where do you see yourself five years from now?

Same place. Founder and CEO of a bigger, better, more successful and profitable Pathbrite.