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Focusing on Federal: Interview with Pluralsight

by Nick Sinai

Entering and growing in the federal market requires experienced executives. This is the third in a series of interviews with Insight portfolio executives about the federal market. In this interivew, Insight Senior Advisor, Nick Sinai, speaks to Mike Smith, Senior Vice President of Sales of Pluralsight.

Tell us about your career history.  How did you get into working with the federal government, and federal sales?

I started selling to the Federal Government directly out of college.  My Federal sales career began at Oracle Corporation where I was trained on how to sell to the government which is a science onto itself.  Just because you have a shiny object that they undoubtedly need, it doesn’t mean they can acquire and leverage it.  I also learned a lot about the importance of a sales culture.  Oracle was a work hard play hard culture.  I think they got it right and it showed in the flawless execution of the sales team quarter over quarter.

Where is Pluralsight in its efforts to serve the federal government?  Why is the time right for the federal government to adopt your technology?

Pluralsight is a technology skills platform.  Our platform allows technology experts to develop the skills they need to create progress through technology and develop the skills of tomorrow. While our company only began a concentrated effort to sell to the Federal Government about three years ago, most cabinet level agencies are already customers.  Like any industry, the Federal Government can greatly benefit from greater technology skills training and assessments.  

What would you tell a management team thinking about entering federal?

Make a sizable investment, hire experienced resources and be patient.  Almost every technology company wants a piece of the Federal pie because of its large addressable market of $ 90B in IT spend.  What they don’t know is that they will need contract vehicles, product compliance, experience sales and marketing talent and a lot of patience as they work through a protracted sales process.

What are some misconceptions about federal sales that you’d like to clear up?

I’ve had the opportunity to represent many Silicon Valley tech companies trying to enter the Federal market.  Most want to enter because of the large addressable market and most feel because they have had success commercially those results will come naturally in government.  This truly isn’t the cause and often involves significant changes in product, legal, finance, marketing and sales.  Some things are non-negotiable and there are no guarantees.  You can’t go into it thinking

you will change the way the government conducts its business.  You have to embrace the process because you will never change the process.  

How would you describe the partnership with Insight Partners?

I find having Insight as a partner such an added benefit in building and driving a Federal sales team.  Nick Sinai has been great in offering input on our overall Federal sales strategy and marketing investments.  I view Nick as a trusted ally willing to offer guidance and participate in driving successful outcomes for our team.  Our team has a great working relationship with Nick and has figured out just when pulling Nick into our opportunities will have the most impact.  Nick has numerous executive level contacts in government who have been essential in helping with many of our enterprise deals.

What do you like to do when you aren’t at work? 

I love to exercise and spend time with my family when I’m not working. I have a 12-year-old daughter who plays travel soccer and competes in school track meets.  I find it very rewarding seeing her lead and participate in team competitions. For me, what I learned growing up competing in sports translates so well to your professional career.  I try to run or bike each day.  I appreciate the mental benefits of exercise just as much as the physical.  It’s amazing how many professional problems I have solved during a run.

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Nick Sinai

Nick Sinai

Senior Advisor

Nick Sinai is a Senior Advisor at Insight Partners. Nick works with existing portfolio companies in the data and software sectors, and identifies new opportunities for investment in these sectors. Nick also advises portfolio companies on policy, regulatory, and government markets. Nick is…

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