Catching up with “Tau Tank” Veteran Kyle Cushing ’11

cushingLast spring Kyle Cushing ’11 was one of four ATO presenters at our “Tau Tank” networking lunch in Chicago.  He talked about his startup, ClearContract.  Here’s a quick update…

Kyle, for those who weren’t at the “Tau Tank” event, tell us a little about ClearContract and what progress you’ve made since that event?

First, thank you Dane for revitalizing the alumni community.  It has been great to get to know GZ’s from multiple eras.  For me it has led not only to multiple friendships but also a number of fruitful business relationships.

When I spoke at Tau Tank we were pre-product, pre-revenue and still very focused on solving a niche problem for a niche industry.  Now we are working with Microsoft!

In the last year we’ve launched with a number of paying customers in the financial services space and have grown our employee base by 2.5x (what I really mean by this is we have grown our team from 2 to 5 J).  Our team is currently in Seattle working with Microsoft to expand our product functionality and distribution channels.  We’re leveraging the Microsoft Office suite to make it easier for attorneys and business professionals to manage their contract negotiations, regardless of length or complexity.  Our market segments are expanding from solely focused on financial services to in-house counsel, commercial real estate, and consulting.

Note: Check out a brief interview with Kyle on the Weekend Web: April 26, 2015

What are some of the toughest challenges that you’ve been facing as you’re getting this new company off the ground and how are you addressing them?

Getting in front of the right people.  The industries in which our product will add the most valuable are some of the harder industries to penetrate.  We are addressing this through a variety of ways…thought leadership, partnering with Microsoft and spending lots of time with our customers to understand their deepest pain points.  Above all of this, building strong relationships has proven to be the most effective way to address this challenge.  The ATO network has been fantastic in this regard.  I’ve developed some strong relationships and mentors through the fraternity, and the brothers have been more than willing to help.  In fact, just the other week, Pat Jensen made an introduction to someone who could potentially be our biggest client to date.  Big shout out to PJ!

What are some of the most rewarding experiences you’ve had working with ClearContract?

The whole thing has been fantastic.  It’s a rollercoaster…enjoy the ride.

We heard that you were recently selected by Microsoft to take part in a four month accelerator program which they sponsor in Seattle.  How did you get involved in that?

I began having discussions with Microsoft in October of last year.  Microsoft Word is at the center of 99% of document negotiations, so I knew that given our space we were going to run into them at some point…the question was whether running into them would leave us completely destroyed or empowered to grow.  Under Satya Nadella’s leadership Microsoft has been going through a massive shift in strategy over the past few years to become a services based company that “outsources innovation”.  When we began talking to them about integrating Microsoft Office into the ClearContract product they were extremely excited about it.  We positioned ourselves as an extension of the Office suite, and both parties saw the logic in us participating in the accelerator to make that happen.  We had strong support from Microsoft leaders in Chicago and from very successful entrepreneurs in the Chicago ecosystem like Howard Tullman.  That got us to “Jury Day” in February, when Microsoft brought out their top 40 companies out of the ~700 who applied.  We spent the day pitching and meeting folks…they saw us as a clear fit and we couldn’t agree more.

Tell us more about that program.  How long is it?  What is the commitment on your part?  What does MS do?  What is MS’s motivation for doing this?

The program runs for 16 weeks and is comprised of 14 companies who are building products to increase productivity in the workplace.  Microsoft provides each company with $25,000 (they don’t take any equity), access to their internal teams, mentorship on both the technology and business fronts, access to their products/tools and a beautiful workspace in the heart of Seattle.  The two biggest benefits for us is access to their 1,200-person in-house legal team and mentorship from enterprise sales veterans.

I come from Deloitte Consulting, which is a massive company, but it is spread out across the globe.  Microsoft is obviously global, too, but I never really appreciated the scale and mass of the enterprise until I stepped foot on Redmond and realized there were over 120 buildings.  It is extremely humbling to be considered a part of this.

As I mentioned previously, Microsoft is going through a major shift in strategy and the accelerator program in large part reflects this.  They are looking for innovative companies to bring into their ecosystem and simultaneously aim to attract development talent back to their technology.  It is a fantastic program and thus far all parties have benefitted immensely.

Kyle's workspace at Microsoft - Go Hawks!!

Kyle’s workspace at Microsoft – Go Hawks!!

What’s a typical day/week look like as a part of this program?

Each week is divided into a sprint that is focused on a specific subject (technology, product, customer development, pitching, etc.).  The days vary massively.  The only thing that is pretty consistent is the consumption of beer and whiskey J

Who are some of the other most interesting people/companies that you’ve met as a part of this program?

It’s tough to pick just one; there are a ton of talented entrepreneurs here.  If anybody in interested in getting in contact with a specific company, feel free to reach out and let me know.

Here’s a link to an article about the companies in the program –  “Deconstructing the Accelerator: Meet the Startups Accepted into Seattle’s Second Cohort”

As for some of the interesting people I’ve met, the former VP of Sales for Echosign is a mentor for us, we’ve had dinner with the creator of Microsoft Project, the guy who built Sunrise (the new Microsoft Outlook for mobile) and the guy who created Apple’s Map application.  I have not yet met the man himself (and highly doubt I will), but we did see Mr. Gates’ house on a boat tour J

How much longer is left and what are your goals for the remaining time that you’ll be in Seattle?

We just finished week 6, so have 10 weeks left.  We have three primary goals:

1.)    Production release of the next iteration of our product
2.)    Piloting the product at 10 additional organizations
3.)    Kick-off our next round of fundraising

Is this something that you’d recommend to other ATO’s who have startups?  If so, what sort would qualify and how would someone get involved?

It depends on a number of things that only the founders of the startup can answer.  Where are you with your company?  Is your product ready?  Do you have a solid founding team in place?  Is there an identified need in the market?  Does this particular accelerator align with your business objectives?

My recommendation is to go at it without the help of an accelerator for at least the first year of your company’s lifecycle.  At the end of the day the success of your company is still on you.  You still need to build your product and close deals.  The point of the accelerator is to take promising companies and accelerate their growth.  You need to learn to walk before you can run.  I can say with confidence that doing a program like this last year when I pitched at Tau Tank would have been a crucial mistake…we weren’t mature enough in our lifecycle to be able to take advantage of all that the accelerator has to offer.

What sort of businesses do you think would find value in your services and if an ATO is involved with one of these, how would they reach you?

Any business that negotiates contracts.  Specifically, any business that deals with a high volume and/or heavily negotiated contracts.  From an industry POV, professional services companies can benefit greatly.  Our current clients see anywhere from a 20-50% decrease in the time it takes from initial document release to signature.  Investment Banks, Private Equity Groups, Financial Services, Consulting, Commercial Real Estate and In-House Counsel can all benefit.

Feel free to shoot me an email at or give me a call at 630-673-5953.

Moving away from business a little bit… how did you get involved with ATO?

I grew up in the west suburbs and one of the older guys in the house, Mike Persak (’07) used to umpire my little league games.  We went to different high schools but stayed in touch, and when I went to Illinois he brought me to the first event.

What were some of your favorite memories from your time on campus with ATO?

Three stick out to me:

1.)    The best times were the mornings after a big event.  Everybody eating breakfast, exchanging stories and laughing about the prior night.  Those were the greatest.
2.)    Rush.  I was rush chair for a number of semesters and those first three weeks of the year were always very rewarding.
3.)    A team of us as Sophomores entered into the Deloitte Consulting Case Competition.  People laughed that “frat guys”, let alone young ones, were participating.  It lit a fire under our asses.  We cranked away for that whole week, walked into the pitch and walked back to 1101 winners.

Who were some of the most memorable characters and do you stay in touch with them?

We just graduated 4 years ago and are all still really close.  Technology has enabled us to keep in touch regardless where we live…we have guys in our class in Chicago, New York, Washington DC, Indianapolis, Philadelphia, Vegas and Seattle.  We use a group text with pretty much our entire pledge class, and people banter back and forth daily.

What are some things that you learned from ATO that are helping you as you work with ClearContract?

Perseverance and that it’s OK to ask for help.  The house is a competitive bunch, but at the end of the day everybody had (and still has) each other’s’ backs.  We always pushed each other to do better while on campus, and that has translated over to our careers.  At the same time, nobody has all the answers, and there are a number of guys who I look to regularly for guidance about issues I’m facing at work.

Are there recommendations that you have for undergrad and new alumni who are interested in getting involved with a startup?

Just do it.  Until you go all-in, you’re not going to give it everything you have, which puts you at a significant disadvantage against others who will.  Take the risk now and don’t fear failure.

From a practical standpoint, get out of your comfort zone.  Go attend networking events.  Take advantage of the awesome programming that Dane & co puts on for ATO alumni.  Go check out 1871.  Read the news.  And, most importantly, always be building relationships for the long-term.  A GZ who I met at Tau Tank is now one of our investors, a company advisor and a personal mentor.  We kept in touch after that event and, a year later, he’s now part of this.  It’s awesome.

Is there anything else that you’d like to say to your ATO brothers?

Love and respect.

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Posted in ATO Alumni News, Congrats, In the News.

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