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Debbie Madden
Debbie is a serial entrepreneur and a senior executive in tech. She has built 5 companies from the ground up and is currently the Founder & CEO of Stride (, where she specializes in helping tech companies with complex needs. Stride's focus is two fold: Guiding leadership teams to drive lead generation and marketing strategies. And, working with technical teams on legacy system rewrites and new product development, using Agile software development techniques.

Prior to Stride, Debbie was the CEO of Cyrus Innovation, an Agile software development consulting firm. She grew Cyrus into 60-person, a multimillion dollar, 5 time Inc. 5000 Fastest Growing Private Companies winner, and Crain's NY Best Place to Work. Debbie is a sought after public speaker and writer, appearing in The Wall Street Journal, Forbes, Fox Business TV, The Huffingpost, Inc Magazine and more.

Entries by Debbie Madden

Growing a Tech Startup: Knowing When and How to Scale

(0) Comments | Posted April 24, 2015 | 8:34 PM

Starting a company is thrilling and terrifying all at once. I can only describe it as "energizing stress." I've started and helped start five companies in my career, each one having similarities to those before it. One of the biggest lessons I've learned is that it's absolutely vital to know...

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Binary Bias: Recoding Women's Place in Technology

(0) Comments | Posted April 17, 2015 | 3:13 PM

How do you solve a problem like Maria, especially when our hypothetical heroine has a knack for computer science and radiates all of the key qualities of a technology leader? By all accounts, Maria solves a lot of critical problems on her own.

In every aspect of...

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How to Ace a Developer Phone Screen With a Non-Technical Screener

(0) Comments | Posted April 6, 2015 | 2:54 PM

Maybe you've made the decision to leave your job and are on an active search for your next gig. Or maybe you're passively looking to see what's out there. Either way, it's very likely that your first interaction with your next potential company is going to be with a non-technical...

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Sheryl Sandberg: I'm Adding a 4th Point to Your TEDTalk: Choose to Stay Your Way

(0) Comments | Posted April 2, 2014 | 10:58 PM

Sheryl Sandberg's 2010 TedWomen talk entitled "Why we have too few women leaders" offers three pieces of advice to women who want to stay in the workforce:

1. Sit at the table.
2. Make your partner a real partner.
3. Don't leave before you leave.

I agree...

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Intrapreneur Playbook: 3 Stages to Achieving True Buy-In

(0) Comments | Posted March 18, 2014 | 6:33 PM

Both intrapreneurs and entrepreneurs are catalysts for true change. And since change is disruptive by its very nature, everyone must respect the impact that true change can have on an organization. One big difference between intrapreneurs and entrepreneurs is that intrapreneurs must care about the infrastructure they are disturbing. While...

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Why I Agree With Marissa Mayer

(25) Comments | Posted February 27, 2013 | 5:47 PM

Marissa Mayer's decision to abolish Yahoo's work-at-home policy has grabbed a lot of headlines in the 48 hours since its publication. The decision, clearly a newsmaker because of the scale and clout of Yahoo's operations, has also roused a debate on the importance of workplace collaboration versus worker productivity.


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