Stephen Legler Bio Highlights


I am a tenured professional at Microsoft and recently celebrated my 20th work anniversary (as of January 2021). I’ve held a number of roles over the course of my career; working with customers across the spectrum of Enterprise, Corporate, and Healthcare accounts as well as our customers in the State & Local Governments.

I have deep roots in our business and technology solutions and have always been focused on business growth, optimization, and streamlining operations. As such, I’ve had the honor to be in leading roles such as:

  • Enabling Business Opportunities with Data, Analytics, and AI (April 2019 – present) – I’m responsible for working with our named customers to grow and optimize their business through Sales, Marketing, and Operations. Microsoft is a market leader in data management, analytics, and business intelligence and I leverage this expertise to help organizations transform and grow their business by streamlining their data, analytics and artificial intelligence platforms. I accomplish this with five key principles – Time to Value, Reduced Complexity, Cloud Economics, Maximize Investments, and Faster Business Decision Making.
  • Improving Workplace Productivity with First Party Solution Experiences (September 2013 – April 2019) – I was responsible for working with our customers to streamline their customer/citizen engagement, increase end-user productivity, and improve employee retention and satisfaction. I covered 21 states within the State and Local Government sector with a primary focus on Microsoft Surface and modernizing the employee workplace experiences.
  • Optimizing Workforce Operations -(July 2010 – September 2013) – I was responsible for streamlining and optimizing workforce operations through client technology enablement. Primary focus was end-user client experiences, security, deployment, upkeep, and efficiencies across large enterprises and global organizations.
  • Delighting Customers through Direct Relationships (July 2005 – July 2010) – I was responsible for being the front face and business leader to our Top 5 Healthcare customers in Michigan. Primary responsibility was listening to our customers business challenges and opportunities for growth to identify solutions that could streamline operations and provide a ROI in their investments of our solutions. Additional responsibilities included teamwork orchestration and collaboration, large and complex contract negotiations, best practice development and sharing, and streamlining internal operations.
  • Growing Operations through Partner Relationships (September 2002 – June 2005) – I was responsible for being the partner business manager for our Top 4 partner relationships in the territory. Primary focus was to work with the Partner Executives on business plan development and execution which included the ability to enable, align, and train their sales force to build relationships within Microsoft and with our joint customers. Additional objectives included market expansion, technical and solution skills growth, and executive networking.
  • Senior Infrastructure Consultant – January 2001 – September 2002

I am passionate about the work I do and the engagement with our customers. Sometimes criticized for wearing my “heart on my sleeve,” I actually take that as a badge of honor. I truly enjoy putting myself in my customers shoes and getting to know them and their business. As an example, I had the great honor of being a mentor with Microsoft’s MySkills4Afrika program (an opportunity for me to visit Kenya for 2 weeks helping to jumpstart their devices business). I had the opportunity to meet with executives at banks, professors at universities, leaders at not-for-profits, and was able to setup a customer tour and a day-in-the-life with Karirana – The Home of Eden Tea. If you are interested in my customer experience, I posted it here.

And that is my passion… working with our customers and creating experiences. I love our leadership and our direction under Satya Nadella. I cannot agree with him more when Satya says “Empathy make[s] you a better innovator.” (source)

At this stage in my career, I find it most rewarding to mentor and coach new team members that join the organization. Sometimes it can be overwhelming with all of the new people and processes that you just need a little help planting your feet so you can do your best work — and to achieve your own professional and personal goals.


On a personal note, I’ve been married to my wonderful wife for over 20 years. We have 3 adopted kids. Sixteen years ago, we adopted two 6-yr-old boys from Kazakhstan and four months later we became legal guardians of my wife’s 15-yr-old niece. We went from 0 to 3 kids in 4 months.

Misty and I are from Louisville, KY but have resided in Michigan for the last 18 years. I still hate the cold weather. I am a Louisville Cardinals fan, but will root for the Kentucky Wildcats during March Madness… then Michigan State then Michigan (sometimes… I am just anti-Big10).

I have 3 main hobbies:

  1. I’m an FAA 107 sUAS (small unmanned aircraft systems) “pilot.” I use pilot loosely. Basically, I am a certified drone operator. You can follow along from the “The AeroDrone Experience” section of this site.
  2. I am passionate about Personal Finances and helping others to start their path to Financial Independence and Freedom. This was birthed out of Facebook posts over the years and a desire to help encourage high school and college graduates to begin saving for their retirement. My heart truly breaks when I read articles stating that half of older Americans have nothing in retirement savings (source). I hope I can help change at least one person’s future. You can follow along from the “FIRE ME Today” section of this site.
  3. I enjoy running/jogging. I’ve been slacking the last 1-2 years for many reasons and I look forward to picking it back up during 2021 and beyond. If you have a Garmin watch or log your activity on Strava, look me up and let’s motivate each other.

Thanks for reading. Hopefully our paths will cross. Until then, I wish you many blessings and success in your professional and personal goals.



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