Working at InsightSquared | Glassdoor

InsightSquared Overview

Boston, MA
51 to 200 employees
Company - Private
Computer Hardware & Software
Unknown / Non-Applicable
InsightSquared is the most-awarded provider of sales intelligence solutions for high-growth technology companies.
InsightSquared helps sales operations professionals break the cycle of spreadsheets by equipping them with actionable, real-time reporting on virtually all ... Read more

InsightSquared – Why Work For Us?

InsightSquared was named #1 overall for Sales Analytics as well as #1 in satisfaction and usability for Business Intelligence by user reviews site G2 Crowd.

Fast-growing technology companies recognize the strategic value of sales operations — but delivering that value first requires ops leaders to break the cycle of spreadsheets.

Enter: InsightSquared. We provide visual, actionable reporting on virtually all sales KPIs to empower sales operations to help leadership forecast more accurately, better manage sales pipeline, equip sales managers with the insights needed to provide individualized rep coaching, and advise executives on planning and analysis.

We’re headquartered in Boston, MA, where we are consistently named one of the best places to work.

Who are we?

We’re a team of driven, problem-solvers. We’re positive. We work hard to “get to yes.” We’re nimble. How nimble? Our product and engineering teams have completed more than 150 sprints.
We care deeply about sales analytics, data visualization, SaaS, and Boston sports. We’re also hiring.

  • Product Managers
  • Financiers
  • Sales Geniuses
  • Entrepreneurs
  • Marketers
  • Designers
  • Engineers
  • Customer Support
  • Engineers

Why InsightSquared

InsightSquared is a Boston-based growing startup that's reinventing the way businesses are run and at the same time dominating the traditional BI establishment.

  • Multi Award winner for BBJ best place to work and Boston Globe Top Place to Work 3 years running!
  • We're established, with a SaaS product that has hundreds of customers and is bringing in real revenue.
  • Active sponsor with non-profits supporting local entrepreneurs and startups.
  • We're funded by a team of great investors who believe in our vision.
  • Actively involved in community outreach by working with partners like TUGG and supporting the local Boston startup scene through work with Resiliant Coders, and ICW.
  • We've built a place where our team members want and love to be.

InsightSquared Reviews

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Fred Shilmover
36 Ratings
  • "Amazing place to build a career"

    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Former Employee - Sales in Boston, MA
    Former Employee - Sales in Boston, MA
    Positive Outlook
    Approves of CEO

    I worked at InsightSquared (Less than a year)


    -Culture of learning and development
    -A reinvigorated focus on learning and development
    -They are on the cutting edge of industry trends (account based marketing and customer journey, for example)
    -Fantastic reputation and brand
    -Really smart tech and a great target buyer to work with
    -Even after all these years, they still bring the perks
    -CEO genuinely cares
    -I’ve made lifelong friends at this company
    -They run such a smart process that you leave so much better equipped for your career than if you’d chosen another company to work for
    -I’ve seen lots of people advance their career here; some leveling up 3-4 times
    -They promote from within
    -They take diversity and personal safety/happiness very seriously
    -You just learn so much here


    No matter what a company does to try and make it easier, startups are hard. Don’t do startups of you can’t handle the daily struggles, changes, and slips that these companies face.

See All 46 Reviews

InsightSquared Photos

InsightSquared photo of: Ramp 2017
InsightSquared photo of: George's Island
InsightSquared photo of: First-ever user conference - Ramp 2017
InsightSquared photo of: Kickball team 2017
InsightSquared photo of: Summer Outing 2016: George's Island
InsightSquared photo of: Volunteering with Tugg- Tech Gives Back!
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InsightSquared Interviews



Getting an Interview

Getting an Interview




  1. Helpful (1)  

    BDR Interview

    Anonymous Interview Candidate in Boston, MA
    No Offer
    Neutral Experience
    Average Interview


    I applied online. The process took a week. I interviewed at InsightSquared (Boston, MA) in December 2017.


    I had a phone intro that went well; the hiring manager seemed impressed with a couple of my questions.

    I took a 30-question Wonderlic (logic/vocabulary/mental math) test and a personality test online.

    I'm not trying to be arrogant but I'm confident I scored highly on the Wonderlic test based on the practice test I took. I only mention this because they halted the interview process solely based on my personality test. I could understand and appreciate using a personality test to operate better in the workplace and empathize with coworkers, but it feels weird to use it as a gatekeeper.

    I find it unusual that there seems to be no gray area. I feel like personality is something you can easily determine from an in-person interview--salespeople *understand* people, after all. I wonder how many people they're missing out on by ensuring candidates fit a certain mold on this test.

    Even if this practice typical, that doesn't make it reasonable.

    Interview Questions

See All 17 Interviews

InsightSquared Awards & Accolades

  • Best Places to Work(Small Company), Boston Business Journal, 2014
  • Best Places to Work, Boston Business Journal, 2013
  • International Business Awards - Best New Product or Service of the Year - Business-to-Business Products(Bronze Winner), Stevie Awards, 2012
  • Business Intelligence Solution - New Version(Silver Stevie Winner), Stevie Awards, 2014
  • Best Places to Work - Medium-Sized Company)(1), Boston Business Journal, 2015
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