This week the weather in Boston took a definite turn: our extended summer has finally ended and fall has arrived with its usual flourish of stunning foliage.  While I was admiring Boston’s fall look through the windows of my new office on the 29th floor of the Prudential Tower, I thought I’d take a minute to tell you all about our new offices and what moving here means to us.


We’re actually in the process of adding and upgrading several offices as Rapid7’s continued explosive growth stretches our existing space to the limit, but I’m focusing on this particular move because this is where I’m based, and because moving to “the Pru” has been a Rapid7 ambition since we first moved to Boston in 2002. Back then the company was still very small and we knew we needed to grow enormously before we could move to the Pru, but it remained a gleam in our eye nonetheless. 


In many ways moving into the new office symbolizes the transformation we’ve made (and will continue to make) as we’ve grown and matured.  We started out as a small company with a big dream and an outsized work ethic: do whatever it takes to build the best security software in the world and make our customers successful. We’ve grown through many phases over the years, hitting countless milestones that each marked successes that turned formerly aspirational goals into expected outcomes. On the sales front, we saw goals fall like $1M/year, $1M/quarter, $1M/month, to our individual sales teams hitting $1M in a month. 


On the product front, we brought major innovations to the market, such as unified security across web applications, databases, networking devices and operating systems; static code analysis of client-side Javascript; an expert system-based approach that delivers better accuracy and more complete results. We built our Cloud Edition for partners like IBM to provide high scale hosted services, delivered enormous scalability and performance improvements, and introduced our second product line with Metasploit and began transforming the penetration testing space as it converges with the vulnerability management space. 


On the business front, we brought in new disciplines like marketing, channel, a strong process and metrics focus, international expansion, closed funding with Bain Capital, saw both Gartner and Forrester give us their highest ratings, and have been recognized as one of the best places to work in Boston. The new office is a physical embodiment of many of these achievements, but more importantly it’s a statement of our future direction: we intend to become a major player in the security space. Everything we’ve done to date is only the beginning: the best is still to come.


Achieving all of these goals has been a testimony to the dedication and success of our team: all of the Rapid7 family, not just those based in Boston. I want to give you some feel for what our team is like and I thought a fun way of doing that might be to tell you about some of the objects that we brought with us in the move…


Pirate hat.jpgIn my office I keep a pirate hat and sword that Alan Matthews, our founder and chairman, gave me when he turned the helm over to me as the new Captain of the Rapid7 ship. The hat stand is an empty double magnum of a nice California Cabernet signed by the entire executive team and sales leadership from our sales planning offsite in Las Vegas back in 2008 when I first joined the company. They’re fun decorations that provide a continuous reminder of the passion and enthusiasm of the team I’m lucky enough to lead.

Thermometer_m ini.jpg


In the sales area we have a giant hand-drawn thermometer from 2004 – marking a $400,000 revenue target for the year.  Each time the team closed a deal that year, the salesperson would color in the dollar amount of the new sale, filling in the thermometer as the company closed in on the annual goal.  These days each of our offices does a multiple of that in one month, but we keep it around to remind us how far we’ve come and where we want to go – whenever we celebrate a success that feels unbelievable, we reflect on the fact that a few years from now it will be as seemingly small as that $400k appears today. This year, just seven short years after the thermometer was created, we’re on a path to achieve nearly 100x the amount we targeted then.


Lord_Matthews_Cup_mini.jpgWe also have the Lord Matthews Cup proudly displayed in the sales area.  Alan Matthews donated the cup to recognize the top-performing sales office every quarter, and the team created the grandiose name to playfully acknowledge Alan’s British heritage. The cup recently traveled from LA back to Boston, where it currently resides, but I know the LA team is determined to get it back, and even our brand new UK team is joining the challenge.  As you can imagine, the regular cup journeys (or lack of journeys!) are accompanied by a truly impressive amount of trash talking and side bets.


More important though than any physical thing we brought over in the move is the passion, commitment, and creativity every Rapid7 employee brings with them every day.  If you have those qualities too and are interested in joining a very dynamic environment that exemplifies the “work hard, play hard” attitude, check out our careers page for an up-to-date list of open positions in all our offices.  You can also contact us at