Leaders in the Limelight: Selina Winter

Written By

Susan Jacobs

October 17, 2017

My name: Selina Winter

My company: Microsoft

My title: Senior business program manager, Microsoft Certification

My location: My team is in Redmond, Washington. I work remotely from Atlanta, Georgia.

Best business advice I ever received: The best advice I ever received wasn’t so much a direct statement as it was modeled behavior. I learned many things from observing my mentor, who I happened to find at a very formative time in my early career. But the most important thing I learned from her was how to “lean in.” Long before Sheryl Sandberg coined the phrase in her best-seller, Lean In: Women, Work and the Will to Lead, I was privileged to have a strong female role model to show me how to do that. From her I learned to be prepared, confident, and do what we now know today as “leaning in.” Her example and her investment in me as a young professional gave me the confidence I needed to be more assertive and more proactive in inserting myself, my ideas, and my contributions in the workplace. To be clear, it isn’t always easy. But, looking back, I see now how the skills I learned then have served me well in my career and will continue to do so.

Most daring personal career move: Admittedly, my career has not been extremely high on the risk-taking scale. But I do have a couple of moves that felt extremely risky to me at the time. The first was when I transitioned from marketing and communications to a business development position. That move from promoting products to selling products—on the front lines, with a quota—was a huge leap for me. But it was a great move that brought new challenges and helped me gain more skills, particularly in relationship-building with channel partners and customers.

The second was when I made the move to Microsoft. After years of working for small and medium-sized organizations, I wasn’t sure what it would be like to transition to such a large company. (On a side note, I also left business development and transitioned to an operational role when joining Microsoft, which is a pretty far stretch for someone who was a journalism major with a career progression from PR to marketing communications, to marketing, to business development.) But it turns out that moving to Microsoft was one of the best career moves I ever made. And I can see now how the combination of skills I accumulated in my previous roles—in companies of all sizes and in various industries—help in my most recent Microsoft role, which is leading our certification efforts.

What I’m most proud of: Personally, I’m most proud of the time that my husband and I spent as foster parents and of the work we continue to do today to advocate for and support foster children and other underserved and at-risk youth. It is an honor to have the opportunity to help young people who are so impacted by what is happening in their family lives. While foster care isn’t right for all, I would encourage everyone to find a way to help underserved and at-risk youth. There are many ways to help—from supporting a local nonprofit to being a child advocate; from volunteering in low-resourced schools to foster care. This is our future, and leaving the children of today in a better position is a legacy that anyone could be proud of.

Current workplace challenge: Addressing the significant and growing global IT skills gap. It’s a huge problem for individuals who need updated skills to be competitive in today’s workplace, which is increasingly requiring technology skills. It’s a huge issue for companies that have open positions because they can’t find candidates with the required skills. And it’s a huge issue for the global economy.

I’m part of Microsoft Learning, a group at Microsoft that focuses on both training and certification for students and professionals. My personal challenge is how to modernize and simplify certification to attract more candidates. With the rapid pace of technology, our partners and customers need more employees with validated skills to lead their digital transformation.

Something people don’t know about me: This is a hard one. I’m pretty transparent with people I know. So, I’ll go way back. In the summer before my ninth-grade year, I had the opportunity to participate in an exchange program to Japan. As a small-town girl from rural Georgia, it was my first international trip and a truly life-changing experience. In the less serious department, I like cooking Southern food and sharing meals and quality time with friends and family. I also binge watch TV for stress relief.

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