Karen Fassio | Marketing Director | Microsoft

Karen Fassio: Driving the Cloud and AI Revolution

“Technology is embedded in how we live our daily lives so it’s necessary to get to know it, how it works, where it’s going”, asserts Karen Fassio. From owning her first desktop, Atari 600, to now being a part of Microsoft as Director of its One Commercial Partner Group, Karen has inspired many lives. In an interview with Insights Success, Karen Fassio shares her valuable insights of her journey and undulating moments.

Below are the highlights of the interview:

Kindly take us through your journey on becoming a proficient leader in the IT and Cloud sector.

Technology has been an important part of my childhood and early adulthood. My first introduction to a personal computer was with the TRS-80, Atari 800 and Commodore 64. In addition to dial-up into random bulletin board services (BBS), I remember playing early online text-based MUX games accessed through very early Compuserve services. There were so many quests and online character drama! My online character’s name back then was Javelyn.

My first job in tech was with Aldus, a Seattle-based software company that produced an innovative product called PageMaker and coined the term desktop publishing, disrupting the publishing industry in the process. Back then companies were pushing user-level tech to its limits. Fonts had to be installed on your machine and your printer. Designers had to build to the tight limitations of their computer’s memory capacity. You never knew if you would maintain print fidelity with what you saw on the screen. Back then, files produced couldn’t be shared natively across Mac and PCs. While I was at Adobe, I witnessed the launch of Acrobat and PDF (portable document format) and that helped to close some aspects of the Mac and PC divide. It felt like new software innovations were announced daily. I found myself moving and growing with the times rapidly, participating in the early days of broadly available internet, technology outsourcing, scaling that capability as the customer demand grew exponentially. I created campaigns to increase access to technology education all connected to my passion for helping people access technology on their terms. Eventually my career moved in the direction of digital marketing which I see as enabling better communication between people in personalized, empowering ways—which takes me back to where I started in a way.

It has been 21 years since my first day at Microsoft and since then, most of my roles have had some connection to the partner ecosystem, which I love. At Microsoft, we bring technology to people and organizations through our global partner ecosystem. Partners take the technology ingredients we offer and pull them together in a way that serves customers of all types with solutions in all forms. I know that sounds broad, but the fact is, the opportunity is vast and multi-faceted. And now with new innovations in Cloud, AI, intelligent edge, and quantum computing, the space continues to be full of opportunity.

 How do you diversify your organization’s offerings to entice the target audience?

It starts with understanding the lived experiences of your audience and then asking ‘what can I do to improve it?” Fundamentally, be insatiably curious about your customers and the offerings will follow. Naturally, good companies listen to customer voice, observe the market, delve into how products are utilized and make corrections when they aren’t. But how do you know what all that information really means if you don’t know the question you’re trying to answer? To get to great questions, you need diversity of perspectives and a way to invite more questions into the discussion. The right questions make a remarkable difference in what you eventually offer. It was in the book “A More Beautiful Question” by Warren Berger where he shares the concept of ‘question-storming’ rather than traditional brainstorming. This approach creates energy, deepens curiosity, and it’s been a valuable tool for me in striving for limitless thinking.

Marketing seldom focuses on the deep, embedded things that impact the quality of our customer’s business and daily reality. What are we taught? Marketing is product, price, placement, promotion. It’s so much more than that. Marketing can educate, connect, and reinforce your values. Rather than focus on what you can market, direct your resource to how you can add value to your customer’s lived experience.

How do you strategize your game plans to tackle the competition in the market?

Focus on your customer obsessively and you will outpace competition. The time you spend researching competition can be put instead on the things that increase trust and help your customers succeed. Think of yourself with them, helping them win a deal with a customer. Can you provide something they can use to help them bring more value in that relationship?

Not every business has direct access to industry analysts, but everyone has the ability to pick up a phone and talk to their customer. For example, at Microsoft we have forums where users of our technologies have interactive dialogue directly with product developers. Even though I have access to many forms of insights including data, briefings, and analyst research, I make a point to have personal relationships with partners who help me see the space in between all of that. And they learn from my point of view too. I highly recommend creating a way to put yourself side by side with the customers you serve. Challenge yourself to get as close as possible to their day to day. Nothing is as powerful as the voice of your customer (or in my case partner) as you champion change and new ideas.

Technology is all about partnership. In the places that you can’t tackle yourself, can you partner instead? I think that’s why I am so attracted to working with partners and why I love my role at Microsoft so much. As our collective landscape grows in complexity, no one company has all the answers. You need partnerships for innovation, for distribution, for capabilities, for access. It’s through partnerships that we create better solutions and serve customers more holistically. I am constantly looking for ways to bridge those connections and bring more partners into the fold, so we can mix things together with more innovations and opportunities. It’s why I am so passionate about increasing representation in the ecosystem so we can expand perspectives, unlock innovation, and serve more markets.

What are the vital traits that every businesswoman should possess?

I believe Emotional Intelligence Quotient, (EQ) is a leadership superpower. EQ is the ability to tune in to yourself and your emotional state and keep in balance the relationship impact you have on others. How to work with people, learn the areas we need to develop, and nurture is largely underrated in the workplace. There are small signs this is now changing so I’m encouraged. As we embrace rapid change from all sides, EQ is needed and generally, women tend to innately possess this capability.

Over the years, emotional intelligence has given me a different perspective to champion and because it isn’t often practiced in business, it has given me a way to differentiate my impact. I have often doubted the value of EQ because it felt like such a soft skillset. The Harvard Business Review first brought EQ into the limelight in their 1998 article on leadership and it’s been a slow process to getting it fully recognized as a valuable leadership trait. This may be a result of having so few women in tech leadership.

While EQ is tricky to practice and apply in business, as a woman EQ has allowed me to be authentic and purpose driven in how I lead and shape success.

I also encourage women to use their intuition. Most people assume intuition is a superficial attribute. Don’t discount it. Intuition is derived from the synthesis of lots of data. When you consume stacks of information, observe patterns, develop insights over time, you basically create an internal library of reference points that can be applied to new and different situations. Data is the basis for intuition. It’s not just some made-up feeling as we are often led to believe.

As progressive women leaders, we should employ our emotional intelligence and intuition in our role as impactful, future-forward leaders. It’s our superpower.

As per your opinion, what roadblocks or challenges were faced by you in a corporate business? And how did you overcome them?

I have often struggled with having to prove myself. An argument can be won when you are heard, but being treated dismissively or worse, hearing someone else use your words and get support is tough to deal with. When you are shut down despite your best efforts, it makes you question yourself. In essence you’re made to feel excluded from the future.

As a brown, plus-size woman, I am aware that I do not fit the conventional, C-suite executive image. Nevertheless, I am an experienced leader with a track record of doing things that bring extraordinary results and value. I had to set my own bar, find opportunities, and believe in my own value rather than let others define me. It’s helped me see signals that others miss.

I build my tribe and use my network to work at things from different angles and altitudes. The fact remains that this approach takes extra time, energy, and can demand the use of already limited political capital. I know I’m not alone in this experience. How much more effective could we be if we didn’t have to spend time doing this extra legwork? If you notice someone taking a little longer to get to the goals you expect them to achieve, don’t leap to the easy conclusion that they are ineffective. There’s usually something more going on and you should consider the role are you playing in letting that interference continue.

I keep a people-first mindset. I push myself to be the leader I want to follow. I try to do the things for people that I wish someone had done for me when I was in their shoes. When faced with a situation, I ask myself, “What would the leader of my dreams do?” Hopefully in that approach, I model for my team the kind of leader they can also choose to be and when they move on from my organization and go on to lead elsewhere, they have plenty of experience in what empowerment looks like which should give them an amazing advantage.

Have you in any way contributed towards the cause of Women in Cloud?

Women in Cloud has had a huge impact in empowering women with a collective voice and providing access for women who have previously been shut out. Personally, this community has been one of the biggest professional growth accelerators I have ever experienced.

The pace at which I have learned and tested myself through this work has been phenomenal. Women in Cloud not only aligns with my personal values but my career goals too. The process of access creation is harder to do than people realize, and it comes with lots of hard-earned learning. We strive for a billion dollars of economic access for women in this community. This contributes to local sustainability, jobs, and in our representation, we also enable inclusive impact.

As a Women in Cloud founding member and board advisor our drive comes from understanding the lived experiences where women technologists with brilliant innovations were not included as they should have been. We have many decades worth of technology without women represented in it. Hence, as Women in Cloud, we kept learning and adjusting the approach until we figured out a model that works at scale. It’s been 3 years since we started with an idea over coffee. And now Women in Cloud is successfully expanded into new markets.

A community approach leveraging the power of collective action and creating alliances of influence is an essential system. Now that we have a model that works, it’s up to all of us in the community to keep evolving it. It’s not the founding team that drives this. It’s the community that makes thing move faster, broader, more inclusive. I enjoy hearing of other communities tapping into our resources because that is the purpose of this network. There’s plenty of opportunity for all. Use this model. Make it yours. Create impact. And keep it going.

What are your insights on “The myth of meritocracy”? And how it could bring a change in today’s business arena?

The myth of meritocracy reveals the many systems in place that prevent access. Most of us believe in putting in the work, but there are many more schemes designed to keep people in boxes. As we get better at talking about what is limiting progress as a society, it is becoming easier for us to identify these schemes and recognize that old belief systems about working harder do not guarantee success.

Where business can do better is to get curious about the daily working experience of their people. We need tools to help individuals understand their impact, their personal progress and how to apply their talents to the things that matter most. Why don’t we have more women in management? Why are starting salaries so vastly different? Why are opportunities unevenly distributed? Why did it take the women in your organization 5x longer to achieve a promotion? Why don’t women stay in roles as long as their male colleagues?

We have words like ‘glass ceiling’ ‘frozen middle’ ‘covering’ that are a part of our language now because there are very real systems in place that limit access. A woman shared with me that she thought she was doing fine in her career until the day she wanted more. Bang! Her head hit a ceiling. She believed her remaining choice was to leave and start her own firm before she mistakenly agrees to the limited box they defined for her. Those of us who experience this are fatigued by having to explain it repeatedly.

How do you cope up with capricious IT and other technological trends to boost your personal growth?

We vote for what you want in tech by what we use and consume. I’m a digital marketer so I’m constantly looking for innovations in communication and user insight. Though I am in B2B marketing, I enjoy exploring new use cases at the consumer level, and I like to look at the fringes more than the mainstream for insights.

If you are around younger people, observe how they use technology. Think about how painful it is to their personhood to be without tech. The pain rate is more acute for them than it is for my generation by far. What does that mean? How can that influence user expectations in the future? Where are the opportunities to anticipate future services? How will that factor in with your strategies as these users grow up to be your customer one day? What will that mean to brand loyalty, trust, and growth going forward? Is your roadmap accelerating faster than their growing expectations and needs?

What are your future endeavors/objectives and where do you see yourself in the near future?

I am dedicated to creating an inclusive economy. I am honoured to do this at Microsoft, and with Women in Cloud. ‘How can we inspire the solutions that can help us solve the most challenging issues of our age? This is a question that keeps me thinking up new ways to inspire others to join in and participate. I am personally motivated by the United Nations Sustainable Development Goals. We can all contribute to one of the 17 SDGs to help make the world better for all. That’s not just a lofty statement. It’s a real thing those of us in technology can do for sustainability and inclusive impact.