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Gayle Sheppard, Corporate Vice President. Global Digital Transformation, Microsoft Azure

Gayle Sheppard is the CVP of Global Digital Transformation for Microsoft Azure. Prior to joining Microsoft, Gayle has been a successful CEO, and run global business across Asia working closely with some of the world’s largest brands. In addition to her passion for delivering complete product experiences for customers, Gayle is fervid about helping local and global organizations focused on eliminating child trafficking and slavery around the globe.

As she joined Azure Global, I was fortunate and delighted to interview Gayle to get to know who she is, the failures and successes in her journey, find out what motivates her and ask for advice to women in workforce.

Hi Gayle, your achievements as a leader, a top executive, a founder and CEO are truly inspiring! What were your ambitions when you were a child?

Like many of us, I “evolved” into my current state with several milestone ambitions worth mentioning. Surprising to many is that I first wanted to work in ballet, to be a ballerina. I was in awe of this art form but was too tall to be accepted as a classical ballerina, so I studied it as an art form and practiced it in numerous ways in my youth. Today the closest I get to ballet is Pilates as I attempt to exercise some of discipline learned from ballet. Perhaps more notable, I am the daughter of an entrepreneur/building contractor, the granddaughter of citrus farmers and Methodist ministers. I enjoyed this inspiring mix of building, growing and evangelizing at the core of my life. My exposure to construction and farming helped develop an interest in end to end complex systems — what they are designed to do and how to design/build them. Which took me to operations research and finance — the studies of complex industrial problems and systems. And here I found a home. Albeit I have had diverse roles in my career, focusing technology, people, and process on addressing industrial problems has been consistent throughout.

Starting young your focus, drive and discipline is praiseworthy. how did you set about achieving your goals?

Let passion for the “mission” drive the way forward, not money, not status, but the love of the work and the people served. Then, when the time comes, ask, don’t wait to be asked, to take on the next big thing you believe in and want to do.

There are probably several glorious and fulfilling career and personal milestones in your life. What are you most proud of?

There are a couple of things that stick out in this now long career — 1. A year out of University I received a call from my father asking me to consider leaving the software industry for some time to run his construction company. Please consider that I was involved in the family business from the age of 12 and onward in some capacity. And after considerable discussion with my father and my two older brothers, I took on the role. I made lots of mistakes. I survived and as importantly so would the business. The learnings during this time about customers — what it means for a customer to be satisfied, to define expectations that are mutually agreed to and delivered, and learning the art of working with customers to solve difficult problems, are lessons that lived on throughout my work. I think about the diverse work force I was responsible for at this time– not so much in gender, but certainly in race and age. And to be a young woman leading a business of which 95% were men from diverse cultures was an incredible experience. I would return to technology after serving in this capacity for a few years. Another life changing event occurred 15 years later when I headed to Hong Kong to help establish a new Asia Pacific presence for J.D.Edwards. At the time we had a few employees in Singapore and a modest network of reseller partners in 5 of the 15 countries included in the Asia Pacific Theatre. My initial role was to lead various aspects of customer relationships across the theatre — sales, channels, marketing and software delivery across the theatre. We built country MD teams who would then localize these functions for their specific countries and regions. This included two of the fastest growing strategic markets — China and Japan. Michael, my late husband, and worked as a team in this situation and were uniquely qualified to take on this challenge together. After a year on the ground in Asia Pac, Michael would take over Greater Asia while I moved to Tokyo to lead the growth of Japan, both considered at the time critical markets to help J.D. Edwards reach its pre-IPO revenue goals. We were successful in building these markets to a scale needed to support the IPO and to provide for on-going growth in the years ahead. It is impossible not to include working with Michael in Asia as one of the great career and personal milestones. He was a best friend, a colleague, a peer and a mentor. Mike died of cancer in 2013 after a three-year battle. This special relationship and its enduring love and deep respect is one of life’s precious gifts. I am certain that it lives on in my capacity to lead with empathy and compassion as well as humility and fierce resolve every day.

What was the most significant event in your career?

Successfully creating an exit for Saffron Technology, an AI start up based on an associative reasoning platform, that albeit I was not an original founder, I would become the “third” founder partner when I joined two former and brilliant IBM Researchers to figure out how to develop the initial platform from research into a scalable, commercial platform. Our customers included organizations such as the US DOD, Aerospace Companies, Financial Services Organizations and Manufacturing including Intel who acquired Saffron in October 2015. We applied our technology to inspiring missions including my favorites of helping the U.S. Army’s Counter-IED Task Force to respond to the rapidly escalating IED threat in the Iraq War, developing capabilities to identify and manage costly, unplanned maintenance events in the aerospace industry, working with the National Center for Mission and Exploited Children to expand data use for analysis, to helping financial institutions create new customer centric intelligence for fighting fraud and anti-money laundering. The exit event was a significant life event for our employees and a positive event for our investors. The team, the work we did and the customers we served at Saffron has been most memorable and meaningful.

That sounds incredible, thanks for sharing and once again congratulations on a superb exit.

People close to us have a tremendous impact on our success. Who had the biggest influence on you?

Parents who encouraged me to read everything, to seek out the arts, and to excel in school, Mike Sheppard, previously noted, resounding cheerleader and constructive critic, and the following leaders who encouraged the use of my strengths to build teams and businesses, demonstrated servant leadership and encouraged giving back to help others: Paul Covelo (JDEdwards Global EVP), Ed McVaney (JDEdwards CEO/Founder), Craig Conway (Peoplesoft CEO), Manny Aparicio (Saffron founder and neuroscientist). They provided environments and diverse opportunities for continuous learning, growth and meaning that has made the difference in my life, in my work.

I can relate, finding allies in the workplace is critically important to success, a sense of belonging and workplace safety.

On a different note, failure is not the opposite of success; it is a part of success. What has been your biggest challenge and failure?

Developing, growing, nurturing Saffron to be successfully acquired by Intel only to fail at institutionalizing this commercial software into its DNA was my biggest challenge and failure. I learned a ton, assembled a remarkable leadership team who built significant teams and business opportunity for this new generation of AI, and met incredible people at Intel, including Customers and partners who remain friends and colleagues today. It was a rewarding experience despite the business was not a critical go to market capability for its acquirer at the time.

Who you are tomorrow begins with what you do today. What are the secrets of your success?

I have a few simple tenants that I live by. Wake up early for thinking time and preparing for the day. Always make my bed. 😊 Focus on communicating more not less. Commit to practice servant leadership and take on every challenge with humility and fierce resolve. Set aside time for learning — professional as well as the arts, humanities, philosophy. Eat and exercise for your well-being. Find ways to invest in your community. Plan for 7 -8 hours of sleep. And always stay true to yourself and love what you do. Know how to balance priorities and aspirations so you find equilibrium often.

Sleep is the best meditation :) How has your experience in Microsoft been? Can you share some of the things you have worked on and plans for FY21?

In FY20 as CVP, Product Management, Azure Data quick highlights for this vast and fast growing product portfolio included many product launches made during the year, forming the new PM leadership team and cultivating a PM culture, leaning in with the Product teams on their product strategy and roadmaps, digging in on data governance’s role in protecting privacy and corporate assets to make the still large percent of data that is unused today, more accessible, consumable and explainable for decision making, and injecting a passion for end to end AI-led digital decision platforms into the mix.

In FY 21, as CVP Global Digital Transformation for Azure, I am excited to work with the Azure Global team to build upon the great work underway on multi-horizon solution planning across our products and markets to help Customers achieve their aspirations for market disrupting innovation, apps and data estate modernization strategies and the digital and cultural transformations that accompany them.

The new role in Azure Global sounds exciting. What advice would you give to women in the workplace?

[Gayle]Number one when considering this amazing pool of talent that we have at Microsoft is this. This can make all the difference in women’s presence in the workplace, in their communities, and in their lives. When you are in meetings and your ideas are not acknowledged and someone else restates your ideas without attribution, then the best thing to do is to thank this individual for reinforcing your idea. Or if you see this happening to someone else, do this for them if they don’t speak up. Prepare for your meetings, have a thoughtful point of view, be ready to generate ideas as well as discuss those of others. It will make a big difference in your self-confidence — a cornerstone of success.

By failing to prepare, you are preparing to fail. Thank you Gayle for the astute yet actionable advice, it has been wonderful to talk with you! I wish you much luck and success in your new role.



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Vinita Ananth

Vinita Ananth

Azure Customer Engineering at Microsoft. Lead Azure Global Specialized Workloads specifically SAP, HPC, VMware and Legacy. All views are personal.