Successful Berklee Alumni #80: Brian Orlando

Brian Orlando

Listen to the interview (approx 1 hr, 5 min.) or download it.


Graduated in 2009 with majors in Music Business and Performance.  Principal instrument:  guitar.


Position:  Senior Account Executive (sales) at Proofpoint, a large firm specializing in computer security.  Brian is on the “inside-sales” team, selling Proofpoints security packages to large, businesses in the northeast.  He focuses on sales to companies where there’s not yet a business relationship, doing a modest number of six-figure deals each year.


Overview:  While still a Berklee student, Brian used a family connection to get several part-time, commission-only sales jobs as way to make money.  Graduating during the economic depression on 2009, and not wanting to make a living as a performer, Brian spent 6 months looking for a jobs in the music business or other business, without luck.  Finally, he reached back out to these companies he had worked for while in college, one of which offered him a full-time sales job selling quality-control equipment to telecom companies.

Brian worked there for four and a half years, working his way up to more senior positions with better territories, etc.  But he wanted to work in software, so started looking for new opportunities.  He reached out to a friend who worked at Proofpoint, who then recommended him for a sales job there, where once again Brian has done well for himself, working his way up the ladder into better territories and accounts.


You can see Brian’s LinkedIn profile here.  Brian encourages Berklee students & alumni interested in a sales career to reach out to him.  “We need to help one another, and reach out to each other. We’re in this together.”


Choice Quotes:  “One cool thing about sales it it’s really an opportunity to interact & learn about organizations and solve problems–assuming you believe in the product.  If you don’t believe in the product, don’t sell it.”

“Sales is a meritocracy.   If you hustle or slack off, you’ll be compensated that way in the long run.  Also, sales is financially rewarding–base salaries aren’t great, but with the commissions you earn you have the potential to do very well for yourself in enterprise sales, and potentially earn money comparable to a doctor or a lawyer.”

“A good organization will empower a sales person with resources. You’ll be on a team and get support from people who will teach you technology, techniques, etc.”

“Berklee taught me that performing 90% of a song isn’t good enough, and folks will remember the other 10%. I take that same thought process into my business. I learned to be thorough, prepare well, and give it my all.”

“A lot of folks in sales started out as a BDR (Business Development Representative).  There’s a lot of turnover, so it’s pretty easy to find a job. Within a year you’ll be promoted into sales or will be burned out. It’s extremely tough work and kind of a rite of passage. But you’ll get through and you’ll see it’s a real profession. I take a lot of pride in it.”



See the full index of successful Berklee alumni.

Successful Berklee Alumni #79: John Sauer

John Sauer

Listen to the interview (approx. 1 hr, 13 min.) or download it.


Graduated in 2007 with a degree in Jazz Composition.  Principal instrument:  trumpet.


Position:  Software Administrator (official title:  Director of Advancement Services) at MassART (Massachusetts College of Art and Design)  John is the one “techie” working for their office of Institutional Advancement department, which raises money, puts on events, and keeps in touch with alumni.  His roles involve helping people there do what they need to do with the databases and developing new functionality.


Overview:  While still in high school, John was programming his graphing calculator to solve equations.  He considered going to school for computer science, but elected to attend Berklee as he figured tech skills would be easier to pick up later.  While at Berklee, he taught himself more technology on his own time, and was a student employee at Berklee’s learning center, where he developed greatly improved software for internal use.  After graduated, he was hired as a very-part-time contractor to build software for Berklee’s Office of institutional development.  Meanwhile, he searched for a full-time job, initially in either music or high-tech, but broadening the search as the weeks rolled by.

By August he got a job with a small company that made medical software, but he didn’t like the job very much, as the pay was mediocre, the commute was long, and he was very unfamiliar with medical terminology.  However, in the spring of 2008 the person who had hired him for that project created a full-time position and urged John to apply for it, which he did and go the job.  John stayed at Berklee for almost 6 years, getting promoted to asst. director of tech in that office.  In early 2014 one of his bosses went to work for MassART and realized that they needed more tech expertise, so she reached out to him to come to MassART.  It involved a raise and a promotion, so he took the job.

You can see John’s LinkedIn profile here.


Choice Quotes:   “In my experience a degree in a field isn’t as many points on a resume as you mght thing. At least in tech, it’s more about what you can do. What got me hired was a doing a ‘passion project,’ which I strongly recommend. You pick up skills that you got to make it happen, show you’re into it (unlike a required school project), and have something to show off.”


“A good indicator of what someone is passionate about is what they do in their free time. As a Berklee student my free time was spent playing video games, learning about tech/programming, and composing/jamming.”

“I have been doing answers on Stack Overflow, partly for my own benefit as I’d see questions whose answers I’d want to know, and I enjoy the challenge of figuring things out. It’s great I spend half an hour on a question, post an answer check back in a little bit later and 50 people have upvoted my answer.  To get hired, be able to demonstrate that you have the relevant skills. With tech it’s your own project or website or (like me) a score of 4000 on Stack Overflow.”


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Successful Berklee Alumni #78: Jeff Holden

Jeff Holden

Listen to the interview (approx. 1 hr, 15 min.) or download it.


Graduated in 2009 with a degree in Professional Music.  Principal instrument:  drums.


Position:  Sales Representative for Breakthru Beverage Pennsylvania, a major distributor of alcoholic beverages.   Jeff works for the fine wine division, selling to restaurants, bars, and festivals where wine is consumed on-site.  His job involves building and maintaining relationships with the people in these places and getting them to order fine wines from among the 500+ varieties his company distributes.  He earns a base salary + bonus according to whether he meets or exceeds his target sales quota.

Overview:  While at Berklee, Jeff had a work-study job at the admissions office.  After graduating, Jeff moved to Pennsylvania and married his high school sweetheart, who was still in college.  For the next 18 months, he worked full-time at Starbucks while also gigging heavily, earning decent money but putting in truly insane hours.  He also had fun volunteering at a local craft brewery. Jeff reached out to his former boss at Berklee, hoping for a job.  As luck would have it, soon afterward there was a shake-up in Berklee’s Admissions Office and Jeff was hired to design and manage the campus touring experience.

For three years Jeff did that, along the way feeling that his career path was going to be in higher education rather than music.  However, he continued his passion for craft beer at a local brewery.  By 2013, he was ready to move on, and started looking for other jobs.  His wife noticed a job ad for a marketing director at Bauer Wine and Spirits in the Back Bay.  A friend of Jeff’s worked there part time and put in the good word, and Jeff was hired.  For close to three years, Jeff worked there successfully, selling wine to customers as well as developing marketing strategies and campaigns.  Eventually, he and his wife decided to move back to Pennsylvania, and he started looking for work.  A colleague passed his resume along to someone he knew in that area, and Jeff got a call from his current employer, which led to and interview and him being hired into his current job.


You can see Jeff’s LinkedIn profile here.


Choice Quotes:  “My job has two pieces: wine and selling. Wine is the gas the fuels the engine. I’m extremely passionate about anything fermented. I love the experience of different flavors and new things.   I’ve met incredible people who make it or sell it. When it comes to selling, this is my first sales job in this way. It was a risk–I’m not a very aggressive, pushy person. But building a relationship slowly and being genuine and caring about whether my accounts succeed has been very effective and is satisfying. I’ts a real rush to close on an account that you’ve been working on for a month or two.”

“One theme that I’m sure you’ve heard from every salesperson you have spoken with is that all that matters in sales is the relationship and the trust. What it really comes down to is people buy from people they like. I have to be technically proficient, but to make a sale I really need  to make a friend or at least a good business relationship.”

“Maybe 10% of people I meet in the wine industry at all level came to wine through music! The industry isn’t as glamorous as it seems from the outside.  It is hard, hard work, but it is so rewarding if you’re passionate about it! I get to drink things and meet people I never could afford to otherwise.”

“If you’re trying to figure out your career, you need to stop worrying about what everyone else thinks you should be doing and think about what you’re spending your free time doing. If you’re spending it on a non-music hobby, consider exploring that as a career path.”


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Successful Berklee Alumni #77: Matt Boyle

Matt Boyle

Listen to the interview (approx. 57 min.) or download it.


Left Berklee in 2008.  (Completed his liberal arts at Bunker Hill Community College 2011-2014, Finished his very last requirement and officially graduated from Berklee in 2016), with a degree in Professional Music.  Principal Instrument:  bass.


Position:  VIP Support Technician at Massachusetts Institute of Technology (MIT).  Matt is on a four-person team that supports technology for the office of the college president and other top-level administrative people.  “Everything is done ‘from stratch,’ by hand, and on-side with everything double-checked.”


Overview:  Starting at age 11, Matt would make a bit of money by buying computer parts, assembling computers, selling them, and providing technical support.  Entering Berklee as a diploma student, Matt transitioned into the degree program, but left in 2008 due to financial issues.  Matt searched widely for a job in the Boston area, focusing on both being a butcher and learning guitar repair, but his experience led to him being hired at the then-new Apple store as a “genius” (tech support), where he received good training and certifications for Apple products while making decent money.  He worked there for around two and a half years, but grew weary of the long hours and erratic schedule which prevented him from finishing his education, and was sending out resumes.

Nearly a year after he had applied Matt heard back from the MIT-affiliated Whitehead Institute for Biomedical Research, to support their Apple hardware.  He worked there for five years, eventually seeking ways to move up.  MIT was doing a shake-up of its IT staff, and he was offered his current position in late 2015.
You can see Matt’s LinkedIn profile here.


Choice Quotes:  “I like that I get downtime plus access to unlimited sources to learn things.  The users I work with are amazing, fantastic people who have incredible stories!  On the technical side, I really enjoy finding a solution to a problem nobody has been able to figure out.  It’s awesome and I get a real charge out of that.”

“If you want to work in tech support, get lots of certifications.  Your certifications are your resume in tech–it doesn’t matter where you went to school, but your certifications show you can do stuff.  The Apple Store is a great place to start; there days I do a lot with lynda.”

“Put yourself in the customer’s shoes and treat the people that way you’d want to be treated, and you’ll be better than 95% of support technicians.  I got my position because I got a reputation at being really good at working with people, even when they were angry or frustrated.”

“Visualizing something before you do it is the biggest thing I learned at Berklee–where I’d trained myself to figure out where your fingers will go before you play it–that’s just like what I do when I repair a computer.   I’ll visualize the problem, consider the possible issues and figure out how to accomplish the fixes while I’m still walking toward the location with the issue.  Often I’ll be in and out in a couple of minutes and people will think I’m a wizard.”

“I still play music with a band, Monkeys of a Bygone Era, though with my newborn kid.  Anyone who really wants to stay in music, find a lucrative side hustle where you can work less than full time.  Learning to code is a great plan–there are so many jobs.  Many pay well (at least for the next 5-10 years) and you can do it from anywhere.”



See the full index of Successful Berklee Grads.