16 questions with Chicago's Art Shaikh, Founder of CircleIt

16 questions with Chicago's Art Shaikh, Founder of CircleIt

1) Introduce yourself

Art Shaikh: My name is Art Shaikh. I have spent 20 years building successful teams and had a fantastic career at Salesforce before launching CircleIt. I have been fortunate to build a team that has the same drive and passion I have for what we are doing and that has made it fun and exciting from day 1.

2) When did you start CircleIt?

AS: CircleIt was officially launched in 2018. At the time, I still had a full-time job so I was working to build the company until I was able to commit to it full time.

3) Why did you start this business?

AS: Growing up, my father always had his camera around his neck, shooting pictures and videos at every family gathering. Photos would be developed and videos copied – and gifted to family members near and far. He always felt tremendous joy watching people’s reactions to these special gifts.

Over time, he began writing notes, documenting memories, and creating handmade cards that he would stash safely away in a large box alongside his treasured family photos and beloved old home movies.

My father left behind this box overflowing with photos, stories, cards, and gifts for future life events with specific instructions on how and when to share these treasures with his beloved family. He wanted his legacy to live on – and for his family to continue experiencing his love long after he was gone.

CircleIt was built to replicate this unique gift, for my mother to help carry on his legacy, so others can experience the joy it has given all of us, and in memory of my father, Arif Shaikh.


4) How many people do you employ?

AS: We have grown to over 30 employees, with about half working in our Chicago office. We have plans to double that number by the end of 2022. During this “Great Resignation” where tech companies are losing employees in droves, we have not lost one single employee and are continuing to hire more as we scale.

5) What’s a recent success you’ve had?

AS: We wrapped our Series A funding of $5.1 million and have nearly 5 million downloads of our generational platform globally.

6) What is the most interesting thing about your product?

AS: Our technology helps you send cards and gifts to loved ones for any future date or life milestone even long after you're gone. Imagine a mother with cancer that wants to be sure she is there for her child’s wedding. She can create a card today, and even personalize it with a video message, and CircleIt will guarantee delivery for the wedding.

7) What is the most interesting thing about your business itself?

AS: I think the most interesting thing about our business is that we are breaking with the traditional tech model of growing a business. All tech companies are reliant on selling user data to advertisers or third parties to make money, or charging subscription fees. So either you are bombarded with ads on their platforms or they are providing the information to other companies for marketing purposes. We have turned down hundreds of offers for millions of dollars because we know our members want to keep their communication with loved ones private and secure.

8) What are your long-term business plans?

AS: Long-term in the startup world can mean a month in advance, but we are planning some major product releases that will be truly revolutionary. Our Child Account feature will enable parents to create an account for a child that is not quite ready for a phone, or even an unborn child. They can then connect grandparents, aunts and uncles or others to the account and those individuals can send cards and messages to the child that will unlock when the time is right. So picture a grandfather sending some advice for his grandchild on getting their first job after graduating, and the grandchild receiving this advice when it is time to go on that job hunt.

Another major release coming soon will be Smart Cards. These will be cards built for specific milestones where a date is not known. Imagine you are a grandmother with a 2 year old granddaughter. You want to send a card for her wedding day, but you don’t know when that will happen, and you don’t know that you’ll be there. You can create a card today, select the ‘Smart’ option, and then CircleIt’s technology will ensure that card is delivered on the wedding day.

9) How do you take care of your employees’ wellness?

AS: Sadly, it has become unique to simply be human toward employees. But I don’t really look at things from an employer-employee perspective, because I consider these people family. We provide everyone with the things that they need to be successful and happy, and our 100% retention rate over the time we have been in business is a testament to that, and something I am extremely proud of.


10) Will you expand your business more?

AS: We will expand our business on every level in the coming months. We’re in the process of raising a $30 million round of funding, and we will be doubling our employee count. In addition, we plan to add millions of users to the platform as we expand our product and service lines.

11) What do you attribute your success to?

AS: Our success has been driven by finding passionate and motivated people that are experts in their fields. From product design, to communications to marketing and technology, I am a firm believer that we have the very best people in the industry and the results speak for themselves.

12) What do you look for in a good employee?

AS: Believe it or not, I conduct interviews myself. I know that basic skill sets for various positions need to be in place, but what I truly look for is whether or not the mission and technology resonate with someone. Skills can be sharpened and taught, but drive and passion are two things that are innate in someone.

13) What makes what you do unique?

AS: There is not a technology in existence that does what CircleIt can do. At its core, aside from all of the functions and features, it connects loved ones on a level that does not exist in our digital world. When technology that was supposed to bring us together has been dividing us, it is time for a technology where we can all be family again.

14) How does your business adapt to change?

AS: As a tech startup, change is a constant. Pivoting is something we learned we needed to do quickly, so I worked hard to help my team become as nimble as possible.

15) Where in the Midwest are you?

AS: Our global headquarters are located in the River North neighborhood of Chicago, IL.

16) Where can people find you on social media?

AS: You can find us on the following social media channels. By the way, we give away prizes every week to those following us on Instagram. We’ve given away iPads, smart watches and Air Pods to our followers.

Find out more at CircleIt's website, or follow on Facebook, Instagram or YouTube.

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