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4 Copley Place
Boston, MA 02116

Company Overview

InsightSquared’s sales intelligence solution is the “operating system” for high-growth sales teams. It empowers sales operations leaders to help their executives produce reliable forecasts, understand pipeline trends, and maximize rep impact.

InsightSquared is based in Boston, Mass and has been named a "Top Place to Work" by The Boston Globe, and Boston Business Journal.

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What is it like to work at your company in terms of your culture? 

InsightSquared brings the culture pretty hard. Our CEO Fred has made it his mission to make InsightSquared a place where “Squares” want to be more than anywhere else. Everyone we hire needs to be a cultural fit, and we look for the following in potential hires: a collaborative mindset; the need to be awesome; and the ability “to hang”. 

Collaboration is the lifeblood of InsightSquared, and all teams work cross-functionally to be faster and more creative when handling challenges. Have a unique skill that you want to share? Plan a “Brown Bag” Lunch’n’Learn session and teach the whole team. Have an awesome product idea or campaign to run? Grab a team of engineers, marketers, product folk and an office manager and build your plan at a hackathon. 

In addition, InsightSquared looks for “awesomeness” – although it doesn’t necessarily need to be in the skill set you’re applying for. Team members at InsightSquared, or “Squares” as they’re called in-house, want to excel and think bigger than their role. This usually manifests itself not only in their “get after it” attitude, but also their desire to work together. 

And lastly, Squares spend a lot of time together, so we want to make sure we maintain a great “hang out culture” when it’s time to relax for a bit. Grab a beer on tap, play some cornhole (on InsightSquared designed boards) on Fridays, or simply hang “in the Square” and enjoy a free lunch with other members of the team.

   InsightSquared Jobs. VentureFizz

What’s the best way to get a job at InsightSquared?

Do your homework. What do we do? Who do we serve? What could we be doing better? 

Then, show up excited to change the way small and midsize businesses are run! 

When you’re in your interview, ask questions and interview us as well. Understand what a day-in-the-life of current employees looks like. Understand what your role will look like. 

What can someone expect during the interview process?

You’ll meet us at our office right in downtown Copley, and you’ll likely be interviewed in a conference room named after one of the members of the Wu-Tang Clan. 

Many positions here will often have you work on a type of homework assignment, whether it’s provided live in the interview or before you meet with the team. We really want to make sure you can walk the walk, so come with your thinking cap on. 

Many positions here will often have you work on some kind of homework assignment, whether it’s provided live in the interview or before you meet with the team. We really want to make sure you can walk the walk, so come with your thinking cap on. 

What can people expect over the course of their career at InsightSquared?

InsightSquared is focused on growth – both for the business and our employees. Squares who come to work excited to learn and prove their abilities can really shape their career here. Whether it’s taking on new responsibilities on their team, or exploring opportunities across departments, Squares can determine their own success.

InsightSquared has a “promote from within” culture that we place a lot of value on: Many of our best employees have started in one role and grown into another. What we ask when you join the team is that you do your job in the absolute best way that you can. That’s how Squares who move throughout the company have progressed. 

Squares can also expect a lot of opportunity to work with other teams, and get an education in building a SaaS business. With monthly All-Hands Meetings to talk about the business, monthly “sprint reviews” where teams showcase what they’ve built in the product, engineering hackathons, and an entire floor dedicated to creativity, collaboration and “fun”, like Friday hangouts,  new employees will have tons of access to meet and work with everyone on the team.

Are there any favorite activities that the employees do outside of the office? 

We have a number of special interest groups for people to organize activities – and Squares tend to organize over email or Slack groups (climbing@; active@; dogs@; games@; musicians@; brewers@). You can always find someone organizing a weekend run (and subsequent pub hang out), watching a play-off game in the Square, or planning something fun like pumpkin carving, kayaking on the Charles, or ice skating. Now that we’re nearly 200 employees, our team members have developed “Pods” or cross-department groups that coordinate outings to help Squares get to know each other.

In addition, it’s important to our team that we give back to the community around us, so we commit to one day of volunteerism per quarter as a team. We work with TUGG to sponsor and volunteer at local events in the Boston area.

     InsightSquared Jobs. VentureFizz

Are there any fun facts or unique stories that you can share about InsightSquared or individuals that work there?

  • Our co-founder Sam is a polo champion, and recently won a winter polo tournament and funny trophy to boot.
  • Our team rented and sailed several huge sailboats to get to our company outing on George’s Island this summer. It worked out great until the wind stopped on the way home!
  • If you join the team, you won’t be able to have the user name, pickles@... It’s already taken
  • Don’t pick your own nickname unless you actually want it to stick, as our teammate HustleBones found out after our first company-wide meeting

What TV or movie would best describe the working environment and employees at InsightSquared?

Workaholics meets an uplifting Boiler Room meets Silicon Valley meets Dumb & Dumber. With a side of Rocky I-IV. 

Do you have any unique benefits or perks? 

  • Free lunch for the entire office everyday
  • Beers and cold brew on tap at all times
  • Ping pong tables, shuffleboard, foosball, a music room, and Rock Band
  • Unlimited vacation policy
  • Flexible Hours
  • Dinner if you stay late

What’s on tap or in your fridge?

4 rotating taps in The Square, often InsightSquared home brews. Usually a dark beer, an ale, a cider, and a super hoppy/random IPA.  The fridge is filled to the brim with Chobani yogurts and Sriracha.





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