Top 10 experiences as a Microsoft employee

colleenobrien
6 min readSep 5, 2016

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Earlier this summer, I celebrated my five-year anniversary of working at Microsoft. Since hitting the milestone, I’ve been really reflective about my time as an employee at the company, thinking more about what I’ve learned over the past half-decade. I wanted to mark the occasion by documenting the experiences that inspire the most gratitude — the anecdotes that make me thankful that Microsoft took a chance on a film major. While there are MANY more than I’ve captured here, below, you’ll find my Microsoft experience hall-of fame:

  1. Sponsoring the Grace Hopper Celebration of Women in Computing — Nearly one year ago, I flew down to Houston, TX as a first-time attendee at Grace Hopper with a goal to recruit more tech-savvy women to join the Windows Insider Program. The event activation — including presentations by women on the Windows engineering team, a fun photo booth (see above), and a fan-favorite calendar highlighting prominent women in STEM (designed by my friend and colleague Claire Anderson) — ultimately drove over 1000 leads to the program. When the work was executed, I had the opportunity to hear from incredible speakers at the conference, including United States Chief Technology Officer Megan Smith and Facebook COO Sheryl Sandberg. Needless to say, I can’t wait to go back.
  2. Launching Outlook.com with Microsoft’s first ad featuring a same-sex couple — As a very junior marketer on the Outlook.com Product Marketing team, I had very little to do with the decision to create or air this commercial (that credit goes to Raphael Aquino-Jose, Dawn Martynuik, and Dharmesh Mehta). But to witness the inclusive conversations and industry-leading courage that led up to the launch is still a major source of pride, and a highlight of my marketing career.
  3. Creating Achieve More, a Hackathon podcast project — A podcast enthusiast, I capitalized on Microsoft’s annual week-long Hackathon to create and promote Achieve More, an interview podcast through which entrepreneurs and side hustlers alike can share their perspectives on customer obsession, brand-building, and product innovation. The pilot — a partnership project produced by Rick Senechal of Microsoft Production Studios— received some great feedback, and has sparked renewed interest in the medium amongst marketers at the company.

4. Graduating from University of Washington’s Foster School of Business — With an undergraduate degree in film production, I realized pretty quickly that there were some knowledge gaps that might keep me from being truly impactful as a marketer. I enrolled in UW’s Technology Management MBA program — an 18-month-long evening-and-weekend program for technology professionals — to pick up the skills that many of my colleagues had learned as undergrads. My enrollment was really only possible thanks to Microsoft’s tuition reimbursement program (over 35% of my program fees were covered) as well as the company’s flexible work hours and life balance philosophy.

5. Interviewing Chris Capossela, the Chief Marketing Officer of MicrosoftBruce Avolio, the professor for my Leadership Development course (a requirement of the MBA program noted above), prompted us to interview a great leader. I sent a cold email to Chris Capossela, Microsoft’s Chief Marketing Officer, who graciously agreed to a meeting. We spent an hour talking about everything from his first job working in his family’s restaurant, to his experiences as Bill Gates’s Speech Writing Assistant, to his rigor about time management. I loved that such a senior leader was willing to take the time to support a very junior employee.

6. Updating the Microsoft Services Agreement and Privacy Statement — With little more than two years of Product Marketing experience under my belt, I was assigned to lead the communications strategy for a pivotal update to the Microsoft Services Agreement and Privacy Statement that would align five discrete sets of terms into a single user agreement. The project required deep partnership with legal, engineering, marketing, PR, and operations teams across the company — in addition to external agency partners — ultimately culminating in the notification of nearly two billion consumers. While I had worked on scaled communications before, I didn’t really comprehend the size of Microsoft or our customer base until working on this project.

7. Visiting the Microsoft Digital Crimes Unit — Microsoft employs nearly 115,000 people, so — needless to say — I’m constantly learning about different teams or work that’s going on at the company. One of my former Foster classmates who works in Cloud + Enterprise Security at the company organized a “Tech Trek” for us to visit the Microsoft Digital Crimes Unit: headquarters for the fight against cybercrime. This division of the company partners with legislators, law enforcement, and other technology companies to combat everything from botnets to child pornography offenders. This experience exposed me to the scale of cybercrime (as many as 50% of online adults are victims every year, including 20% of small business owners, costing the global economy about $500 billion), and inspired tremendous pride in the work that Microsoft is doing.

8. Working as a “Loaned Professional” on the Microsoft Giving Campaign — I’ve participated in Microsoft’s philanthropic efforts for a few years now, organizing Day of Caring projects, leading an Upgrade Your World clean-up to celebrate the launch of Windows 10, and managing small annual Giving Campaign events for my marketing teams. But this year, I’ve joined the Microsoft Philanthropies team full-time for four months as one of seven “Loaned Professionals” (pictured above with staff at the Mockingbird Society) to help execute the campaign at the company level. As part of this program, we’ve visited several non-profits in the Puget Sound area to better understand the community need, gone through many sessions of presentation coaching (in preparation for speaking to thousands of employees), and learned more about Microsoft’s official non-profit partnerships and programs (including YouthSpark and TEALS). By the end of our four-month commitment, we’ll have helped raise over $100 million in employee donations for non-profits working around the world.

9. Attending an inclusive design workshop — Inspired by Oregon State University Distinguished Professor Margaret Burnett’s GenderMag (a new method enabling software developers and UX practitioners to find gender-inclusiveness issues in the software features they produce), the Microsoft Design team has been evangelizing concepts of inclusivity along behavioral profiles vs. the gender binary in an initiative called “Windows for Everyone.” I was lucky enough to attend a workshop led by Margaret Price and Robin Counts, and encouraged to see senior leaders at Microsoft in attendance as well. While the population of people building technology doesn’t yet mirror the diversity of the global population, it’s hopeful to see a commitment to inclusive concepts.

10. Joining the Microsoft Academy of College Hires — To bring things full circle, five years ago, I joined the Microsoft Academy of College Hires (MACH) alongside passionate, tech-loving college grads from around the world. As we worked through training together, we formed a great social and professional network that traversed the company. Five years later, many of my fellow MACHs have since left the company, expanding my network to the tech hubs of New York, San Francisco, and beyond. Flipping through my digital Rolodex, my MACH classmates are making their way as founders, C-suiters, and employees at companies like Twitter, LinkedIn, Box, and Button. We continue to stay in touch, share tech news, and support one another in career planning.

Phew! Five years, ten amazing experiences — and those are just the highlights. My Microsoft wishlist (things I want to accomplish or experience at the company) continues to grow week over week, so stay tuned for the next episode.

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