Ruler: Jeremy Bergeron



The Short Story: Jeremy is a college athlete turned sales executive for a technology company known as the “Bloomberg” of the Commercial Real Estate Industry. He’s been on the job for six years, and is on the verge of beginning the next phase of his life, which includes starting a family.

Biggest College Fear: “Everything up until graduating college was kind of like a script. There’s a syllabus in some form or fashion; whether it’s coursework, how your degree program works, where you’re going to live — the steps are all laid out. Once you finish college, the roadmap disappears, and that’s intimidating. There’s no one pushing you in a direction. Now, it’s all on you: your choices, your finances, your success, and your failure. Without a structure; there’s only the path you make.”

Virgin Business Lesson: “Schedule time with any Executive willing to do an in person informational interview. Whether you simply get the opportunity to ask questions or build a relationship, learning from the people who have tenure and experience is invaluable.”

Industry Uniqueness: “Commercial Real Estate is a big money industry with finite players and limited opportunities. Type “A” personalities make the environment competitive and at times, cut throat. It’s a numbers driven business and success is based on ROI. Regardless of whether you are a servicer or a day-to-day person in the business, compensation is based on how much effort you put in. I like that because I control my destiny–I reap what I sow.”

Right Now YOU Should Be: “Practicing your presentation skills. The kinds of jobs you pursue fresh out of college rely on communication skills. In fact, success in the recruiting process depends on your ability to articulate your value to the company and potential co-workers. It’s all about pitching skills.”


About a year into my collegiate baseball career, I realized playing professional sports wasn’t going to be my path.

In high school, my priority was baseball, not academics. I chose the junior college route because it allowed me to continue playing ball. But as Scouts began to evaluate and recruit players, it became clear which athletes were in demand. As the injuries mounted, and my body became less stable, I realized I needed to shift the focus to school, ace my coursework and figure out next steps. It was a huge learning curve for me, but fortunately, my junior college had an honors program with a great filter system to larger Universities. In college, I was totally focused on getting a job in the sports business.

I thought internships operated like college; that it was the entry gig to your dream career.
After graduating from Berkeley, I did internships with the San Francisco Giants, The Golden State Warriors and the Recording Academy, determined to make my dream of working in the sports and entertainment business a reality. But internships don’t pay—and with student loans coming due, rent, and other financial requirements I connected with a tech recruiter who helped me start my current career.

I thought internships were another structured path just like college, where you get the internship, then the full time job offer, prove yourself and eventually get to do what you really want in the company. But that’s not always the case, especially in the sports business. There are a finite number of full time jobs, and internships are often bodies to fill part time work.

During my dream internship with the Giants, several front office executives were willing to speak with me about my goals. I envisioned being a Senior Executive for a professional sports team someday, where I’d be able to steer the ship. But I wasn’t sure of the path to reach that goal. Every single Executive I spoke with, including the CEO suggested I pursue sales whether I chose to stay with the team, the industry or went elsewhere, because as an Executive you are always selling yourself or the business.

Any job or internship that had the word sales in the title I automatically dismissed; didn’t even read the description.
When I was looking for jobs in college, I specifically avoided sales. Back then, it seemed like your entire job was to bother people by pushing unwanted products or services. I had a total misperception of the role. Sales is extremely entrepreneurial. You have to find the product or service that fits your personality. I like the company I’m at because I’m merging different products to create unique customer solutions, so there’s variety in my role. We only deal with C-level executives so I’m involved in problem solving for decision makers and get to challenge my brain. You get access and broad insight into how companies work—not just the company you work for, but also client companies. If you’re self-motivated, sales is a great way to control your own compensation and learn any industry.

In sports, you drill a skill in front of a coach until you perfect it.

Success in sales is earned through the same discipline you develop in sports—repetition. Anytime I’ve had trouble with any aspect of sales, whether it’s trying to learn another vertical, working on a pitch, handling objectives, or how to network, I’ve sought out someone who knows how to do it better. I’m a believer of asking questions to folks who know how to do something the right way, with the intention of taking the feedback to get better. I’ll ask for one on one time with a more senior sales rep, or the sales management team and drill, so to speak, until I perfect the skill. Some sales people may just float; try to figure things out on their own or on the fly. But that approach means putting opportunities at risk, potentially damaging a chance to earn the business. For me, it’s just easier to ask, learn, and have a trusted solution at hand.

Now, I pay attention to the higher conversations happening in the company. When I started working, my focus the first few years was to learn sales, the products and the industry. We’ve grown organically and through acquisition to be a large publically traded company with about 600 sales people and 4000 plus employees. It paid off to keep my head down and really master my role. Today, even though my job doesn’t have direct reports, I’m running a team of about  15 people and providing support at all levels of the company. Sometimes, I’m asked to sit in on more strategic conversations like competitive strategy, product improvement, staying at the forefront of the industry and partnerships. I’m learning what it takes to grow a company successfully. Rather than being compartmentalized in a given role, I always want to be in a position where I’m learning and growing.

Six years ago my criterion was about pay, a cool ideas, or a more challenging role. But now I’m facing the unknown, and it’s scary.
At 29, I’m heading into a new phase of my life, and forming different priorities, especially around family. How to evaluate the next opportunity is a big question, especially when you aren’t sure of your direction.

One the one hand, being in sales at the same company for six years, is comfortable. The pay feels good. I’ve earned status, recognition, and achieved goals. Where I am has been a great start. But as I’ve begun the process of writing one year, three year, five year, and ten year goals, I find myself exploring questions like: Do I want to stay in sales? What would it mean to change industries? What kind of change would compliment me holistically—skills, wants and needs? Change may force me to start over on some level, which affects things like compensation, status, or the ability to negotiate for work life balance. It’s not just about me anymore. My thought process has shifted from satisfying short term gains to thinking about what’s better for the long term; what’s going to make me happy, what can I be proud to put my stamp on in my career and what makes sense for the people around me as I move forward.

Coming out of school, the world is full of opportunity and we believe we can do all things at any given time.
When I think about what makes me happy, undoubtedly, I get super passionate about the sports business. I’m still pursuing opportunities; and when I’ve been on job interviews it’s like I feel my lights coming back on. However, I haven’t been chosen for an opportunity, nor have I found something that’s the right fit. Rejection is hard, especially when your friends and your family know it’s a passion and are rooting for a win. In thinking through my future plans, it feels like I’ve got a window of three years where I can take chances. Pursuing a job in sports will definitely mean starting over—a cut in pay, title, role, and ego. I recognize that it’s ok for me to take a step back in order to leap forward. But again, it’s not just about me anymore. My personal priorities are tied to the Bay Area, which limits my ability to pursue smaller sports markets where getting a start may be easier. To continue to pursue this dream and keep my priorities in place, I may have to start thinking about sports differently to find the right opportunity.

Keep setting goals and stay connected to your network.
Out of school, I think I did a good job of finding mentors or people to bounce questions off of. But once I got a job, I just kept my head down, and got into the day-to-day groove. I wish I’d stayed more in contact with some folks and asked more directly for them to take a vested interest in me.

Also, setting goals coming out of school, even if it was a tentative plan, really helped. Continue to set goals, even as you progress in your career. Think about what makes you happy in life: career wise, socially, family, and financially blends together as you get older. It’s been a relief to step back and figure out what I want for myself even if I don’t have all the answers just yet. The process of planning gives me something to fall back on, while keeping the future in mind.