Since launching our Boston coding bootcamp earlier this year, we’ve fallen in love with the city commonly referred to as "Beantown". And while we could rave about its charming streetscapes and penchant for winning championships, what makes Boston truly remarkable is the depth and breadth of its tech community. With so many opportunities, we turned to Boston expert Paul Gentile, a tech veteran of over 20 years. Paul talks about what it’s like to work in such a dynamic marketplace and shares advice for folks looking to break into the tech scene.

Could you tell us a little bit about you and your career trajectory?

I started out in a couple of different sales roles, including selling office furniture, before I found my way into tech. My first tech job was also in sales working for a company called Course Technology. Beyond providing solutions to customers and prospects, I really fell in love with the company’s overall mission to rally around change and find new ways to embrace technology in education.

From there, I pursued a few internships, essentially internal internships, meaning I found a few cross-opportunities within the organization. Those experiences really wet my appetite for product.

Then I spent the past 11 years at Pearson Education, working in digital strategy and project management. Primarily my career has revolved around championing the voices of customers and finding ways to create solutions for them. I developed award-winning products, launched new products, revamped older products, and found ways to connect the dots for educators and students. Chiefly, I strived to create a deeper appreciation for the pains and gains our customers face on a day-to-day basis.

After about a decade at Pearson, I realized I was hungry for change. Several different organizations were trying to recruit me to run product but those positions didn't necessarily feel like the right fit. I chose to work at LogMeIn and took on the role of Senior Director of Product Marketing. I've held this position for almost six months and what initially attracted me was the high-pace, fast-paced nature of the SaaS environment and also the pedigree that comes along with LogMeIn. I'm currently managing the product marketing efforts behind their flagship products like GoToMeeting as well as several other products within the communication and collaboration portfolio. It’s been an amazing, rocket-fueled experience thus far.

What initially attracted you to the Boston area? And did you imagine that you’d stick around as long as you have?

It’s actually a pretty funny, sappy story. Boston was this hub for the job market in general. The scene also had a little bit of that post-college feel to it because of all the different higher-education institutions that are in the Boston area. But the driving force behind my decision was my girlfriend, who is now my wife and the mother of my 3 children. She is originally from this area and we met in college.

LogMeIn is headquartered in the Seaport / Fort Point District, which is home to many tech companies. What are the benefits of working in an area with a large cluster of tech companies?

Part of the draw of working for LogMeIn was the Seaport/Fort Point district. It is still referenced as the Boston Innovation District and continues to blossom with talent. It’s served as a model for all sorts of different firms trying to enhance their brand and their facilities in an effort to attract top talent. If you want to continue to have award-winning products and services, you have to attract the right people and make them never want to leave the office, right?

In terms of networking, what’s the tech community like in Boston? Is it informal? Can people just meet at a bar or coffee shop? What are your recommendations?

I encourage people to explore the particular field or role that interests them most. For example, I knew I wanted to stay in touch with customers. I knew I wanted to develop messaging and give clients a voice inside the organization. I understood that this involved marketing so I researched different types of marketing technology. I searched for networking opportunities, some of which were formal but didn’t have the type of stuffiness you might expect. I'd also go grab coffee with people. I'd go to an after-work cocktail hour that certain organizations were sponsoring. I tried to give a sense of my own style and personality. Sometimes I just swapped virtual business cards with the new contacts. Other times, I continued the conversation in different channels like LinkedIn. Beyond that, I think just grabbing a drink with colleagues and talking about some hot trends may lead to something. People are more than willing to strike up a conversation in any atmosphere, especially if you focus on the right pockets of industry in the city.

How did you find out about these types of networking events? Is there a centralized place where industry people post information?

Searching online is definitely one of the easiest, low-hanging fruit options. There's all different forums, discussion boards, and social media channels where people are constantly promoting things and announcing events.

I’d definitely recommend District Hall, a public workspace in the Seaport District. It’s essentially the café area, or main congregation area, in a building where several startups operate. There are boards and messages posted regarding different things going on within the scene. They also offer their own innovation community events. Just as an example, this morning, they did a Salary Negotiation Workshop over coffee.

What is one thing that folks outside of Boston or new to Boston should understand about its tech scene?

For one, the Boston tech scene continues to grow and it's bursting at the seams. There’s established players like LogMeIn, which has been around for 10 years and has over 3000 employees, and there’s all different types of startups. You've got the opportunity to find your particular niche and explore that in a deep, passionate way. Secondly, there are several different pockets of technology that you can work in no matter what your specialty or field of interest. LearnLaunch, for example, is an EdTech startup incubator space that promotes different solutions in various sectors. In most other metropolitan areas, there are only one or two specialties that the city focuses on as a whole. But Boston has many different options available to prospective employees, especially for those that are hunting for their next opportunity.

It sounds like you need to be somewhat specific about what you're looking for or it might become overwhelming.

Yeah, you have to focus on one of two things. Firstly, ask yourself: what particular field do I want to work in? Is it education technology? Is it financial technology? Is it the communication collaboration space? Conversely, you might want to focus on [on a particular functional area]. You may not be married to a particular industry or vertical, but you know you want to be in marketing technology, product development, product management, or engineering. With either route, you have all these different options laid out in front of you.

Boston is home to 12 unicorns. That's not even including all the thriving public companies like LogMeIn. Is there something that the city is doing that has fostered all of this growth? Or is there a more organic reason for the city’s success?

It's a combination. Boston is unique in the sense that there's a heavy higher-ed institution footprint here, which allows for creative individuals to jump-start their career immediately after college. Despite the cold weather, people flock here because of the schools and they stay here for post-education opportunities. And with the way that technology's completely revolutionizing everything that we do, it's almost embedded inside all the different pockets of the city. This can take the shape of a startup, it can take the shape of a well-established unicorn, or it can be something that somebody might dream up and start in the basement of their apartment in Dorchester.

Secondly, there is that organic element. This city has a blue-collar mentality. Part of the city’s DNA is also made up of hard-core east coast-style people that want to succeed. And because of that mindset, the tech scene has exploded in the Boston area. Not only is Boston a blue-collar city, it's also part of a progressive state. From a political stance, we're welcoming to anyone and everyone. That's truly part of what the city is all about and what Massachusetts as a whole is recognized for.

We see now how it’s a combination of the two.

Yes and you can trace [that duality] back all the way to when country was founded here. The city has this progressive first-mover attitude, but at the same time, you've got people really working hard.

From everything you’ve said, Boston sounds like a fantastic place to launch a tech career. To conclude our interview, we have a few final questions. We’ll call it a lightning round.

1. What's your favorite publication to stay informed about the tech community?

Probably TechCrunch.

2. How about your favorite bar to meet tech people in Boston?

City Tap.

3. What's your favorite neighborhood in Boston to explore?

Harvard Square or Back Bay.

4. If you had some work to get done on a Saturday, where would you go?

The Thinking Cup, which is loud and rambunctious. It's often got a lot of people within the scene buzzing with ideas about different hot trends. Secondly, if the weather's nice, I'll just go sit out in Boston Public Park.

So many great places for us to check out. Thanks Paul for taking the time to speak with us.

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