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Engineering Spotlight - LinkSquares

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LinkSquares is the first AI-powered end-to-end contract lifecycle management platform. 

We connected with Eric Alexander, Chief Technology Officer, of LinkSquares to get an inside look at the company's technology, various projects, the team's culture, and more. 

Quick Hit Details

  • Year Founded:  2015​
  • Number of employees: 60
  • Number of engineers: 17
  • Industry: Legal Tech

Can you share a summary on what LinkSquares does?

LinkSquares helps legal, finance, sales and marketing teams work smarter across the entire contract management lifecycle. The AI-powered contract lifecycle management platform provides end-to-end support -- beginning with pre-signature contract drafting and approvals, all the way to surfacing key insights and analytics into executed contracts. LinkSquares saves companies hundreds of hours and thousands of dollars by eliminating manual contract review and reducing the need for outside counsel.

What are some of the different technologies that the engineering team gets to work with and at what scale?

LinkSquares web applications are built using Ruby on Rails, React, and GraphQL. We deploy to AWS (ECS/Fargate, RDS, S3, ElastiCache, and more) and use Terraform to manage it. We use a number of external services to monitor system health, including Datadog, Rollbar, and Pingdom. Source code lives in Github, with automated tests running in CodeShip.

On the data science side, we have machines in-house that we use for model training. Without getting into too much detail here, it’s Python/TensorFlow. We build our own custom models and deploy to AWS SageMaker, which has been fantastic for us.

What are some of the interesting projects that the engineering team is tackling?

With the data extracted through our AI capabilities, we have a huge opportunity to help legal teams take action on events related to their executed contracts. We’re working on making that data available to them in the tools they are familiar with and in the format they need. Our job is to deliver value to our customers every day by listening to their feedback. Software is just a means to an end. This creates interesting projects related to data cleansing or deduplication, transformations, API integrations, and visualizations. We’re experimenting with state-of-the-art natural language processing techniques to continue improving our AI performance for our customers. 

Does your engineering team have a chance to work on projects outside of their day-to-day responsibilities? 

Absolutely!  When I look at our system today, I see so many pieces that started off as skunk works projects - there’s Signature Detection, our vision-based AI component to identify signatures in a document; our SmartOCR technology; our first Salesforce integration; and our use of Terraform to manage infrastructure. All of those started as an idea that one of us had and decided to run with.

What is the culture like at LinkSquares for the engineering team? 

We have a blog post that goes into more detail, but at a high level it’s four things:

  • Caring more about the customer than the coolest new framework
    • Our job is to deliver value to customers every day. We solve their problems and make their lives easier. Software is just a means to an end. If you get excited about making the customer excited, LinkSquares may be a good fit for you.
  • A sense of urgency
    • Our job is to deliver value every day. Not tomorrow, not next week, and not next quarter. Today. If you have a sense of urgency to solve problems and deliver functionality quickly and see your code in action ASAP,  LinkSquares will feel like home.
  • Collaboration
    • Two heads are better than one; many hands make light work; with enough eyes, all bugs are shallow. These are more than just poster-slogans at LinkSquares. We collaborate everyday on almost everything. We use peer code review, not because we don't trust each other, but because it makes everyone's code better. Engineering regularly consults with Design to brainstorm solutions because it makes for better solutions. If you like all-star team-ups and learning from those around you, LinkSquares is your happy place.
  • Flexibility
    • The regulatory environment changes. The technology environment changes. The economic environment changes. Pandemics happen. LinkSquares -- like all startups -- thrives by being nimble, so engineering projects can shift direction (or be shut down entirely) pretty fast. You have to be OK with seeing your hard-earned software improvements put aside when new projects are prioritized (or when pandemics hit and we have to adjust our engineering roadmap for a Zoom-centric short-term future). If you are always ready and willing to move onto the next big challenge, LinkSquares will give you that opportunity.

What can a potential employee expect during the interview process?

We are hiring here at LinkSquares! We're going to spend our Series A money on hiring good people to do challenging, interesting work. We’re looking at technical fit and culture fit, based on the four aspects of our culture I mentioned previously. At the same time, we know that you’re also interviewing us. We’ll give you as much time as you need to ask questions about LinkSquares. It’s important for us to know that you’re walking away from the interview with everything you need to make a decision about us. During the interview process, you’ll meet several members of our engineering and product teams. In our current environment, this is all remote over a Zoom or Google Meet session. 

Are you involved in any local tech organizations or Meetups?

It’s different in the COVID world, but in the past, you could find us at Boston Ruby Group and Boston React.

Rapid Fire Q&A

What’s on tap?

Cold Brew, Kombucha, and New England IPA.

Star Wars or Star Trek?

Star Wars - the engineering team saw the last two episodes in the theater together.

iPhone or Android?


Coffee - hot or iced? 


Favorite employee perk?

Flexible working hours & location

What TV show describes the engineering team’s culture?

The A-Team!

What music is playing in your office?

We’ve got a slack channel where folks post what they’re listening to throughout the day. It’s a bit of everything - pop, electronic, 90s rock, jazz, funk, bluegrass.

View from your office

My office at home is usually a mess, but it gets the job done.

Cleanest desk 

It doesn’t get much cleaner than Kiran’s:

Team Profiles

Wyatt Greene LinkSquares

Wyatt Greene, Senior Software Engineer

Wyatt joined LinkSquares in December 2019. Previously, he worked for many different Boston-based companies, from small startups to large established companies. One of his favorite things about working at LinkSquares is how easy it is to take initiative. He joined the team wanting to make an impact, and that’s exactly what he’s done. He was given a project and then given the opportunity to run with it. He also noticed quickly that everything is customer-focused and there is an open culture -- teams are easy to collaborate with and that is not something he takes for granted.

Kiran Nanjundaswamy LinkSquares

Kiran Nanjundaswamy, Machine Learning Engineer

Kiran was introduced to LinkSquares when he met co-founder Chris Combs at a Christmas party in 2017. He was finishing his Masters in Computer Science at Northeastern and told Chris he was studying AI and Machine Learning. He interned at LinkSquares the following summer and built a signature detection algorithm that is still used in the product today. He was excited to become a full-time employee after graduation in 2018. Kiran appreciates that the team is given complete ownership of their projects -- once they are assigned a challenge they have the freedom to run with it and opportunity to solve it. Being on the team as it has grown from two to 15 individuals, he is excited about the great group of engineers, both as people to work with and people to hang out with (virtually, for now). Kiran strongly believes that the opportunity to wear several hats in the company tremendously helps in both personal and professional growth.

About the

LinkSquares is the first AI-powered end-to-end contract lifecycle management platform. 

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