Kelly Fitzsimmons, Serial Entrepreneur: Lessons Learned Whilst Raising $8m

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Kelly Fitzsimmons is the Co-Founder & CEO of HarQen, whose award-winning Intelligent Voice Service enables meetings, interviews and other conversations to be captured, enriched, organized and shared.

After the sale of her fourth company, Kelly leveraged the proceeds to found HarQen in early 2007. Under her leadership, HarQen assembled a top tier team and launched their first product in December 2007 and the HarQen platform in 2009, which includes Voice Advantage, voted Top HR Product in 2010, and Symposia, an innovative voice collaboration tool.

Prior to HarQen, Kelly founded, led and sold several companies generating positive returns to investors at Sun Tzu Security and Neohapsis. She received her BA from the University of Rochester and a Masters degree from Harvard.

We spoke to Kelly about the lessons she learned whilst raising $8m for her business; the five concepts at the core of her business; and why we should stop sabotaging women who self-promote.


TNW: Who were your first customers and how hard was it to attract them?


Creating something from nothing is a shamanic fête and it's what is expected of every startup founder.  

The customers are what take a great idea from concept to reality. Our first customers were impossibly hard to land, as we were wandering in the backwaters of market creation.  We had to find a use case that resonated with our market and then find budget in the midst of the Great Recession.  I am still amazed that we were able to sign on such impressive early clients as Adecco and Randstad.  It's not usually the big guys that buy first.  That said, they were the only ones with budget during those years.

TNW: What is next for your company?

KF: We are now entering the rapid expansion phase of our growth curve.  In 2011, PricewaterhouseCoopers awarded us the Silvertip Award for the Angel Capital Association portfolio company most likely to reach $500MM within 5 years.  Thanks to our relationship with companies like Oracle, Telefonica, and Dell, we can see our path to that impressive milestone. 

TNW: When you built your team, what were the key qualities you looked for to ensure the success of your business?

KF: Team building is one of the hardest aspects of startup life.  There are lots of competing elements that work against a young company gathering an A+ team, particularly market and product immaturity.  Top talent wants to know that they will be on a winning team.  With the high failure rate of startups, it's hard to make a logical and compelling case that you will be one of the success stories.  So here are my best strategies:

  • Don't outsource recruiting as CEO.  The talent of the team will make or break you.  Be prepared to dedicate your efforts to attracting and wooing the best people you meet.
  • Plan for painfully long recruiting cycles.  Most of our current team was recruited over a period of years, not months.
  • Be honest of the risks. It's easy to oversell your vision of the future.
  • Try sample projects and see how it goes. Our VP of Business Development worked as an advisor for a year before joining.
  • Look for chemistry first. The right skills are table stakes.
  • A winning team is made up of winners. Make sure everyone has something to crow about in their past.

TNW: Have you come across any other exciting startups recently and what is it about them that appeals to you?

KF: Thankfully, I am always in contact with amazing startups.  I love entrepreneurs, particularly the ones who have failed hard and early in their career.  I have had the pleasure of befriending many startup CEOs and helping them weather the invariable storms.  

My key insight here is that you need to be prepared to be uncomfortable for unreasonably long periods of time.  That's just the nature of a startup.

My favorite startups today include POPVOX, NewsIT, and Current Motors. (Full disclosure, I am an investor in Current Motors.)

TNW: What are the advantages of gender diversity in a startup? Are there any disadvantages?

KF: Any business needs a diversity of perspectives - gender is just one way to get it. HBR just released a study on gender diversity of startups where I learned two things: 1) it is a MUST have in a startup... I may have always felt this way but couldn't prove it prior; and 2) only 1.3% of venture-backed startups have a woman founder and 6.5% have a woman CEO - I'm both and that makes me as rare as chicken lips.   

TNW: What have you learned the hard way through the fund raising process that you wish someone had told you at the beginning?

KF: I have raised $8MM to date for HarQen, which puts me in a small community of founders, particularly women founders. Fundraising is a humbling and sometimes downright humiliating experience. And it is relentless.

In my experience, a startup CEO cannot outsource or hire a fundraiser. If you cannot do it, you should not be CEO.  

And if you think you are good at it, you are not.  Good fundraisers are always trying to figure out how to hone and build their skills, which requires hours of coaching and mentoring.  It's a paradox. You have to be confident enough to do it and humble enough to ask for help.  And if you are a woman, you are going to deal with some power dynamics that make reality TV look positively tame.

TNW: How has your leadership style changed over the years, and why?

KF: I am far more aware of my shortcomings and personal failings today than when I started. To provide some context, I have been a startup CEO for almost 20 years and am still learning how to be a good one.  It's an impossibly hard job given all of the competing dynamics.  When I first became a CEO, I was 25 and was lacking at it.  Thankfully, I ran a privately held company and no one other than my employees, family and a few coaches got to bear witness to the ensuing mayhem.  

TNW: What is one lesson you would like to pass on to other women leaders?

KF: Based upon my very unscientific personal experience, I find that women tend to be self-doubters instead of self-promoters.  

We tend to even put down other women who we consider to be self-promoters.  It's like "those women" are breaking the girl code and must be punished.  

We need to stop the sabotage and actively support those who are trying to get ahead - ourselves included. 

TNW: Tell us a little about the businesses you founded and sold before you co-founded HarQen. 

KF: Prior to HarQen, I founded Sun Tzu Security in 1996 as one of the first pure-play information security firms in the country.  After merging with Neohapsis in 2003, I ran the combined companies until 2006.  Neohapsis was bought later that year, which was a nice exit for the founders. I leveraged the proceeds and started working on HarQen 30 days later.  Along the way, my ego got the best of me and I started two other companies - neither of which faired well. 

TNW: What key lessons have you learned during your entrepreneurial journey and have gone on to apply to founding and running HarQen?


Just a couple key concepts that sound cliché, but are at the core of our business. 1) Hire slowly, only work with the best. 2) Don't ever work with jerks - even as investors. Satan was an angel too…

3) Give more than you get - karma works in both life and business. 4) Know when to walk away from a deal before you start negotiating. BANTA (Best Alternative to a Negotiated Agreement) is your friend. 5) When presented with a choice between being right or kind, chose kind always. 

TNW: Briefly describe the step-by-step process you went through to develop your new initiative, Hypervoice, from the initial idea to the current day.

KF: Hypervoice is still evolving; it's a community effort. HarQen is just one small part of a much larger force at work here.  My contribution here is as the evangelist.  Martin Geddes was the genius who gave life to the concept.  My role has been finding partners to help us accelerate the market adoption and definition of the concept.  

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