InsightSquared Company Overview
InsightSquared helps revenue operations professionals make better decisions by equipping them with actionable, real-time intelligence on sales and marketing KPIs. Businesses rely on the company’s solutions to forecast more accurately, better manage pipeline, tailor rep coaching based on individual performance, understand their marketing attribution, and conduct data-backed planning and analysis.
InsightSquared is based in Boston and has been named a “Top Place to Work” by The Boston Globe and Boston Business Journal. InsightSquared was named a leader in the G2 Crowd’s Business Intelligence Platform Grid℠, ranking #1 in customer satisfaction for the fourth year in a row.
Jobs at InsightSquared
Fred Shilmover is the CEO and co-founder of InsightSquared. He’s helped grow the revenue intelligence company from a single spreadsheet into one of Boston’s premier tech startups. Fred is a board member of TUGG, an organization that brings together tech entrepreneurs with social enterprises that support at-risk youth.
Chief Technology Officer
Geoff brings 20-plus years of leadership experience in SaaS, technology and engineering to InsightSquared. He previously served as the CTO at Valore, where he oversaw and managed every aspect of the organization’s technology including software and infrastructure engineering and architecture for all platforms and products, and prior to that as the CTO of Gemvara and Bullhorn. Geoff received an B.A. at the University of Massachusetts at Boston. Geoff enjoys tennis but isn’t very good at it, and also loves to mountain bike with his two sons.
GM and VP of Product
Matisha comes to InsightSquared from Mautic, a marketing automation startup in Boston where she served as VP of Product. Prior to that, she held various roles in Sales Operations, Marketing Operations and Business Intelligence at companies such as Constant Contact, Sophos and IBM. Matisha received her MBA and Masters In Information Systems from Boston University. In her time off she likes to cook, exercise and enjoy the outdoors as much as possible.
VP of People Operations
Jared is InsightSquared’s VP of People Operations, leading the HR and Talent Acquisition teams. Prior to InsightSquared, Jared led HR and Talent Acquisition in the U.S. and Latin America at Sophos, a security software company, where he helped scale the company from a people operations perspective to its IPO in 2015. He has a B.S. in Business Information Systems an MBA in Human Resources from the University of Massachusetts Dartmouth, and is also a veteran from the U.S. Navy.
VP of Sales and Customer Success
Over his career, Steven has built and grown sales teams for early stage to Fortune 100 companies. Prior to InsightSquared, Steven led sales teams at Dynatrace (formerly Compuware/Gomez), Viridity Software (acquired by APC, a Schneider Electric company), and Marathon Technologies (acquired by Stratus Technologies). He also held leadership positions at Hewlett Packard Company where he relocated internationally. Steven received his B.S. from Michigan State University and attended the Leavy School of Business at Santa Clara University.
VP of Services
Niall is a services veteran, with more than 20 years of experience building, leading and scaling services and consulting teams in the digital search, merchandising, analytics, mobile, IOT, and web sectors. Throughout his career, he’s managed large-scale services teams and engagements for clients including LG Electronics, Whole Foods, Walmart, Walgreens and Best Buy. Prior to joining InsightSquared, Niall served as the VP of Customer Success for Swirl Networks where he was responsible for pre-sales, customer on boarding, consulting, support and customer success. Niall holds a bachelor’s degree in Computer Science from Wentworth Institute of Technology.
Paul has held senior finance positions at numerous scaling technology companies over the past twenty years, including NetGenesis (acquired by SPSS), ATG (acquired by Oracle), ITA Software (acquired by Google), Silverlink Communications (acquired by Welltok), and Localytics. He began his career at Arthur Andersen LLP. Paul attended Babson College where he received both a B.S in Accounting and an MBA.
VP of Marketing
KC brings 20 years of experience in building, leading and scaling high performing marketing teams at growing software companies. Prior to InsightSquared, KC lead award-winning marketing teams at XebiaLabs, Telerik and SmartBear Software. KC is a revenue operations thought leader and has spoken at multiple industry events, including: Marketo’s Marketing Nation Summit, Hubspot’s Inbound Conference, SXSW, MarketingProfs B2B Summit and Marketing Sherpa’s Lead Gen Summit. KC received his B.S. in Marketing from Syracuse University and his M.B.A from The University of Virginia’s Darden School. In his spare time, he likes to run, bike and spend time on the water with his family.
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.
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. 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 lunch with other members of the team.
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 Boston, 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 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, biweekly “sprint reviews” where engineering 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 ([email protected]; [email protected]; [email protected]; [email protected]; [email protected]; [email protected]). 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.
Are there any fun facts or unique stories that you can share about InsightSquared or individuals that work there?
- 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, [email protected] 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?
- Monthly free lunch & Dart Game
- Beers, kombucha and cold brew on tap at all times
- Ping pong tables, shuffleboard, foosball, a library, and Rock Band
- Unlimited vacation policy
- Flexible Hours
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.