Vanessa Jupe started her career in web development.

And, as she admits, she always thought she’d be behind a computer, solving problems in code. “That’s how I started my journey,” she tells us. “And then eventually, kind of organically, I moved into product management.”

But between her first gig in product management at DirecTV, and her current role—Senior VP of Product and Design at Clearcover, an opportunity that she discovered through AboveBoard—a lot happened, from challenging transitions to frequent cross-country travels. 

Today, though, she’s exactly where she wants to be. “I knew I wanted to get back to more of a digital-first company,” she says. “I thought, ‘What could I do if I were at a place that already understood the importance of digital?’ I saw the opportunity for Clearcover on AboveBoard, and it seemed like an awesome role. And interestingly, during the interview process, I got even more excited about the role as I talked to the people there. ”

Ahead, we chat with Vanessa about her beginnings as a web developer, joining the AboveBoard community, and much more.

Can you share a little bit about your professional background and experience?

I started off in my career as a web developer. I thought I'd always be behind a computer, solving problems in code. That’s how I started my journey. And then eventually, kind of organically, I moved into product management.

I really got my start in product at DirecTV, where I was hired as a web producer. Product managers weren’t yet a common thing in most companies, which was also the case at DirecTV. So as I started working there, I thought I’d still be developing code, managing the entertainment side of the experience for DirecTV. But instead, they told me I was going to be really focusing on the strategy of entertainment. 

What was that transition like for you? 

It was a really tough transition. The hardest part was moving away from a role where the code I created directly touched the end user. But it was a really wonderful thing for my career. At DirecTV, I got my first team and started leading folks that were focused on TV, movies, and sports, and creating a robust content experience for our web platform.

Eventually, we started focusing on search and discovery of entertainment—so search engine optimization, categorization, information architecture, that sort of thing. And then over time, my team and I worked on the very first video streaming experience for DirecTV:  over the top (OTT) video and on-demand video through our website channel. And then also our mobile apps and things of that nature.

Three-ish years into being there, the company set up its first digital product team. I was promoted into that role while still leading the search and discovery experience for entertainment. That evolved into recommendation systems and profile systems, as well as voice-to-text and natural language processing.

“It was a really tough transition. But it was a really wonderful thing for my career.”

After a couple of years, we moved back to Texas for my husband's job, and I was flying back and forth to Los Angeles all the time for work. It was getting tiring. So I started to look for a role in San Antonio. I ended up working at USAA, which is like an incredible company, super well thought of. I'm a San Antonio native, so being able to work at USAA was always a dream of mine.

I went in as a Director of digital experience for investment products and helped to transition our department into a digital product management team invested in "channel management". I led that transformation and partnered with our HR team to evolve the jobs and skills of the people there. We brought in external training and did a lot of in-depth work. Eventually, I got promoted to an executive leadership role there.

Once you cracked your first executive leadership role, where did you go next? 

About three years in, I got a call from H&R Block. They were looking for a VP to come and lead one of their large functional areas, which is the do-it-yourself tax business.  It was a fabulous offer. I ended up joining them and in the last three years with Block, we've grown our revenue 50% — really, really tremendous growth for the company.

“I started to think, ‘Okay, what do I really want to do next?’”

Last January, I was contacted by another company that I deeply admire. The role wasn't the right one. They reached back out to me in June with a different opportunity. I was very excited about it, but I was like, ‘Gosh, what else is out there?’ I started to think, ‘Okay, what do I really want to do next?’

I knew I wanted to get back to more of a digital-first company. I thought, ‘What could I do if I were at a place that already understood the importance of digital?’ At that point, I saw the opportunity for Clearcover on AboveBoard, and it seemed like an awesome role. I applied and I interviewed. As I talked to the people during the interview process, I got even more excited about the role. 

Once you started looking for a new role, what led you to AboveBoard?

I knew I wanted to continue being in an executive position and growing in my career. I was looking for headhunters and different platforms I could go to to see what other opportunities were out there from an executive perspective. That's how I found AboveBoard.

“With AboveBoard, I have control. I can look for opportunities on my own terms.” 

A lot of other similar platforms are kind of secretive. It’s hard to find information. And some of them charge a fee to join and see what’s available. But what’s really interesting and unique about AboveBoard is that you don’t charge a fee. You can sign up and get instant access to the information. And you know really quickly whether the company is interested or not.