Chris Shipley, CEO, Guidewire Group, Inc: Inequities Aren’t Just In The Corner Office

Chris Shipley is dedicated to the success of technology entrepreneurs, focusing on identifying market opportunities and building value into the most promising young companies. She was the executive producer of the renowned DEMO Conference from 1996 until September 2009. Chris has identified and helped bring to market more than 1,500 products, including WebEx, VMWare, salesforce.com, TiVo, Xfire, Ribbit, and Ironport.

She has covered personal technology since 1984 and has worked as a writer and editor for a variety of technology and consumer media, winning numerous awards for her writing and often has been cited as a leading influencer. She served on the board and past chairman of the Forum for Women Entrepreneurs and Executives (now called Watermark) and is a board member or advisor to a number of early stage companies. 

Her current venture Guidewire Group is a global market intelligence and advisory firm passionate about technology entrepreneurship. Its exclusive focus on early-stage companies and emerging technology markets drives insight and opportunity to its clients and community.

We talked to Chris about the most common piece of advice she gives to startups; about the kind of technology she’s most excited by; and why she believes that “why aren’t there more female entrepreneurs?” is the wrong question to ask.

TNW: Looking back, what was the inspired moment that led you to launch Guidewire Group? Looking forward, what plans do you have for the company in 2012?

CS: Our singular focus at the very beginning is not that different from our mission today: help emerging startup businesses grow more quickly.  When we started, we did that with consulting services, media and events.  Today, we are building a highly scalable software platform that supports mentorship and advisory services for startups and the Global 2000.

TNW: What is the most common piece of advice that you give to startups? Do you find that male and female founders generally need the same, or different advice?

Focus.  Too often, and because they are very opportunistic, young businesses chase too many options, too many features, too many channels.

And because most often they are operating with limited resources, they can’t do all of those things well enough to rise above the competition and sustain that competitive advantage.  It’s far better to pursue one, focused opportunity and execute exceptionally than to do too many things ordinarily.

That advice is universal, regardless of the gender, age, or market of the entrepreneur.

TNW: What are the most exciting start-ups you have come across recently and what is it about them that appeals to you?

Currently, too many developers are chasing the apps market, leaving many of the really challenging business and social problems untouched. 

So when I see an entrepreneur tackling a really hard problem, that gets me excited.  Building a business is hard work, so you might as well use that energy to focus on something challenging and important.   You don’t need to cure cancer, but you ought to feel like what you are doing is really making a difference in your customer’s life.

TNW: Of all the start-ups you have advised in your career, which makes you the most proud? How did you help them to succeed?

CS: It’s really not possible to point out one or two companies.  I’m really honoured to get to work with so many companies at a point in their development when an objective, experienced eye can bring clarity and focus to the business and when a modicum of encouragement and support can renew the entrepreneur’s energy and passion for the business.

TNW: We published an article recently about subscription service startups being the next big thing in 2012. What other trends do you predict for the next year or two?

CS: We’ll see a levelling off of the consumer-focused startup because of the current over saturation on markets like social, mobile, local. 

There is tremendous opportunity in the business market and I think we’ll see the next wave of entrepreneurship tackling tough business challenges by leveraging what they learned in the social consumer space.

We’ll see the Big Data movement get even bigger, but I think it could also get much more transparent as consumers and businesses embrace openness and get excited about the analytics that can be drawn on top of big data sets.

Lots of other categories feed into both of these growth opportunities, from sensor networks to social problem solving.   And on the heels of the consumer startup boom we’re in currently, we’ll see the influence of that experience entering into the enterprise market; business applications will be more social, software and data will be in the cloud, and the interface to that software will emphasize simplicity and usability.

TNW: What kind of emerging technology are you most excited by and why?

CS: I rarely get excited about technology; I get excited by applications of technology, and I get most excited by applications that have the potential to really impact positively the lives of people at work and play.  Look at something like Kahn Academy. http://www.khanacademy.org/  There’s really not a lot of big technology, but that organization is fundamentally changing the way people are learning. 

Or look at what Paul Polak at International Development Enterprises is driving with his campaign for “Design for the Other 90%” which looks to leverage technology and design against the social and economic challenges of the developing world.   That’s stuff to get excited by.

And so are the startups that are rethinking the enterprise application stack, or non-intrusive biometric security, or a more fluid digital currency model, and yes, even those that are working on deeply engaging gaming.

Perhaps more simply said, if the technology impacts people, improves lives, builds value, then it excites me.

TNW: If you could change one aspect of the world of tech entrepreneurship, what would it be?

CS: Shift the focus from funding sources to customers.

Too many tech entrepreneurs are focused on raising money as if that’s the end game itself. 

I’d rather see them engaging customers.  If they shifted focus, they’d build better products, increase the value of their companies, and have the opportunity to raise capital at better terms.

TNW: How has your leadership style changed over the years, and why? What is one lesson about leadership you have learned the hard way, but wish someone had told you in the beginning?

CS: As I get older, I opt to be more and more open and transparent.  I just don’t have room for politics and game play.   I drive to simplicity and clear agreement.  It makes everything -from motivating your team to negotiating complex deals and relationships – much, much easier.  And it proves to be a great filter, too.  You very quickly find out who’s on board with you, who does or doesn’t share your values.  And that allows you to shift your focus to the challenges, opportunities, and relationships that have the greatest value and stop wasting time on those that don’t and won’t likely ever generate value for the business.

TNW: How has Dell or the Dell Women’s Entrepreneur Network assisted your business? What do you see as the benefits of all-women networks such as DWEN?

DWEN is an amazing collection of accomplished business people – and I use the word “people” decidedly.  They are women, yes, but they are business people perhaps primarily within this group. 

There is no pretence that you find in other groups, and there is a genuine candour and openness that encourages a collaboration among members.  The members of this group are women, yes, and perhaps because we are women we share common experiences that shape us as business people.  But I think the great joy of this group is that it is a network of entrepreneurs, first and foremost. 

TNW: Is there anything we haven’t asked you, but you’d like to share with our community?

CS: In the past year, we heard a lot of opinions about why there are not more women entrepreneurs or why it is that fewer than 20 of the Fortune 500 are lead by women CEOs.  It’s a fundamentally flawed question that tends to lead to faux answers in things like the number of women with math and science degrees or some competitive instinct presumably less represented in women.  I think we ask the wrong questions in this debate, questions that further separate men and women.   We should be asking why we suppose that “manly characteristics” make for “better” leaders. 

We should be asking why so few men choose to raise their children.  We – men and women - should question our own deeply, if not acknowledged, prejudices about gender roles.

If we begin to get at some of these core questions, we might find that the inequities aren’t just in the corner office.

The Dell Women's Entrepreneur Network (DWEN) celebrates the wonderful accomplishments of women in business, whilst looking forward at how we can progress and learn from each other. Natural networkers and relationship builders, women have innate flair for entrepreneurship. With DWEN, Dell is helping women in business to expand their networks while offering technology capabilities designed to help them innovate and grow their businesses.

The NextWomen is in partnership with DWEN to bring you a series of 40 interviews with the world's most influential female founders, investors and decision makers: The NextWomen DWEN Interview Series.

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