Season 2 - Ep. 15 | Digital Transformation and the Power of Listening with Microsoft’s Jacky Wright

Nowadays, every business has either become or is becoming a digital business. And it’s not all about technology. Creating the right culture and environment are critical keys to success. Our guest Jacky Wright is a digital transformation mastermind who led the tech evolution in both the private and public sectors, including leadership roles at BP, GE, Microsoft and the British government’s tax department. From the private to the public sector and back again, Jacky has not only led digital transformations, but also served as a role model for others who don’t fit the typical mold.

Here’s a taste of what you’ll hear from Jacky in this episode, in her words (edited for length and clarity):

Jacky’s Redefiner Moment: Early experiences as a woman in tech

I had a part-time job in a bank doing manual work. Over in the corner was an IBM PC. I went over there and saw Lotus 1-2-3, dBase, WordPerfect. I was like, "What is this stuff?"

I automated my work really fast—what used to take me all week took me the press of a button. I got this reputation in the bank of being this little college kid who created these things that made it easier for them to do their jobs. Transformation 101!

They put me in the technology department, where there were mainframe big computers, trading systems—and one woman. She took me under her wing. She always told me, "Watch out for this guy; this guy's a derailer. This one's an influencer," and helped me navigate a male-dominated environment. And that really taught me about what my role needed to be in mentoring and sponsoring throughout my career.

On inspiring digital transformation at any organization

You start by saying, we need to be outcome-focused and understand the art of what's possible. Because you can't lead people to change something they can't visualize. In a company such as Microsoft, I think the tipping point was, how do we make sure we stay relevant? We had a new leader who set the tone from the top with his vision that we needed to be customer-obsessed. The move to the Cloud, from a transformation perspective, is what would help customers transform and accelerate their transformation—so we needed to develop that, drink our own champagne, make sure we learned how to do it, and then tell our customers what that looks like. And then we need to reward the right behavior.

These are steps that apply to every company.. How you apply them may be different, but really those are the building blocks for transformation.

On being an introverted leader I'm still an introvert.

I don't like attention. My comms manager will say, "Jacky, I know you don't want to do this, but you have to." I don't know that I'll ever overcome that, to be frank, but I do know it's important, because role modeling and helping others is part of what leadership's all about.

People are always trying to find ways to understand who you are. At the end of the day, that's what makes you interesting. And you use that to your advantage, not just for yourself, but to help others in the world amplify their voices.

On the issues she sees as a board member

This pandemic has really put front-and-center the need to understand existential risk and apply systems thinking to how they could impact you in many different ways. How many risk discussions did we have pre-pandemic about a pandemic and its impact on the supply chain? Very few, but now they are a core discussion in board meetings.

The next is digital: how can digital help me, from a go-to-market, new product development, operational efficiency perspective; and how can I digitally transform my organization so that I am always staying competitive. And then making sure we have the right expertise relative to cyber.

The final one is the war for talent. Including people from all walks of life, all demographics—that's how we harness the power of talent. Because as I say, talent is everywhere, opportunity is not. We have to remove those systemic and structural barriers so that everyone has an opportunity.

Jacky Wright
Chief Digital Officer and Corporate Vice President, Microsoft US

Jacky Wright is a global technology leader who has made broad impact in business transformation and on social issues. As Chief Digital Officer and Corporate Vice President of Microsoft US, she inspires and leads teams to help businesses leverage technology to drive innovation, adopt sustainable and accessible business models, and digitally transform.

Wright rejoined Microsoft in 2019 after completing a two-year secondment as Chief Digital and Information Officer (CDIO) for HMRC, the British Government tax department. Jacky has extensive experience leading large-scale organizations driving digital transformation and market making solutions.

Her career spans senior technology leadership roles across many industries including CIO roles at Microsoft, BP and GE. As a leader in technology, Jacky uses her broad platform to drive thought leadership not just for the positive impact of digital transformation for business, but also for social, economic and environmental change.

As a woman of color, her passion, advocacy and influence to create a truly inclusive world is demonstrated in the various forums where she regularly speaks on diversity, digital inclusion and the power of inclusive leadership.

She has been widely recognized for her many contributions in technology and diversity, including an honorary doctorate from Aston University, named as Britain’s Powerlist 100’s 2022 Most Influential Black Briton, a 2020 National Diversity Council’s 50 Most Powerful Women in Technology, the Top 100 BAME Leaders in Business, the Top 100 BAME Leaders in Tech, and Savoy Magazine’s Top Women list. She has also been featured in numerous publications, including CIO Magazine and the WSJ CIO Journal.

Jacky is a member of the Board of Directors for nVent plc, Exelixis, Inc., and Russell Reynolds Associates, Center for Global Health Innovation Board, Board of Trustees for Harvey Mudd College, and the MxD Manufacturing Council. She also serves on various technical advisory boards. Previous board leadership has included Prostate Cancer UK, City University London and YearUp.