Michelle Boockoff-Bajdek Of Skillsoft: “You have to pay it forward and model the same behavior to newer colleagues that helped you when you started out”

It’s a valuable key to my success, and I encourage everyone to actively seek out these “human resources.” It’s also important to recognize that it’s a two-way street. You have to pay it forward and model the same behavior to newer colleagues that helped you when you started out. As Chief Marketing Officer, Michelle is responsible […]

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It’s a valuable key to my success, and I encourage everyone to actively seek out these “human resources.” It’s also important to recognize that it’s a two-way street. You have to pay it forward and model the same behavior to newer colleagues that helped you when you started out.


As Chief Marketing Officer, Michelle is responsible for the leading global marketing strategy for the Skillsoft group of companies, focused on driving growth, generating brand awareness and increasing demand for Skillsoft’s solutions among learners, customers and partners. Since joining the company in 2019, she has overseen customer marketing, corporate communications, demand generation, marketing operations and business development.

Michelle brings more than 25 years of marketing, branding and strategy experience to her role. Prior to Skillsoft, she held several executive positions of increasing responsibility in the high-tech sector, including as Chief Marketing Officer of IBM Watson, where she was responsible for marketing the company’s artificial intelligence (AI) products and solutions. Michelle also served as the Global Head of Marketing for The Weather Company, an IBM Business, where she helped companies understand how to anticipate, plan for and ultimately make better decisions — with greater confidence — in the face of weather.


Thank you so much for joining us in this interview series. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My background is really built on the intersection of high technology and marketing. I’ve worked in industries that focus on using technology to improve people’s lives and work, like telecommunications, networking, data management, and now digital learning. And, I’ve often been the only woman in senior management.

I started my professional journey as a product manager, but pivoted to marketing, returning to school to complete my Master of Science in Comms Management. As my career progressed, I had the opportunity to lead both the sales and marketing team at Quaero during a time of dynamic growth. There is nothing more valuable than stepping outside of your role and taking on a new one to build a deeper appreciation for the sales-marketing partnership.

From there, I became the Vice President of B2B marketing at The Weather Company (The Weather Channel), which was soon acquired by IBM. As Global Head of Business Marketing for Watson Media and Weather, I helped organizations build a weather strategy and better understand how to anticipate, plan for, and ultimately make better decisions — with greater confidence — in the face of weather.

Remaining at IBM, I eventually took over as the Chief Marketing Officer of IBM Watson, playing an instrumental role in one of the world’s largest technology corporations, spearheading marketing for artificial intelligence (AI) products and solutions, as well as the Watson brand. There, I experienced one of the most satisfying moments of my career thus far: developing the Women in AI program at IBM.

In September 2019, I joined Skillsoft as the Chief Marketing Officer. Skillsoft, a global digital learning organization, helps companies unlock the potential in their most valuable asset — their people — through engaging content and powerful technology.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

I don’t know that I would use the word “funniest,” but I certainly made a mistake when I was quite young and was scheduled to make a presentation. Although I knew my subject matter and was a naturally comfortable speaker, I didn’t prepare sufficiently. Suffice it to say, lesson learned. Not only have I thoroughly prepared for every subsequent presentation (and I’ve made hundreds by now), but I actually developed and taught a 7-part course: “Public Speaking From A to D (Analog to Digital).” It’s available on the Skillsoft Percipio platform.

In terms of ‘take aways,’ I think the most important lesson I learned from earlier in my career is how important it is to provide first-time managers with foundational training (something I wasn’t given enough of when I was first handed a team to manage). Too often, companies promote their star performers into management positions, but don’t give them the tools and skills they need to be successful. That’s why we developed an entire channel of learning content to help first-time managers build the right capabilities, credibility, and relationships.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I believe that we often follow in the footsteps of those who have inspired us the most. For me, the person who has influenced my career the most is my mother, Betsy Veneziano. She was a pioneer in the field of technology — starting as a programmer for NASA, and then building a successful career as a product marketing and product management executive for several technology companies.

When I think about the leaders who influenced my career, such as IBM’s Caroline Taylor, I certainly remember their charisma, character, and drive to succeed. But those qualities are not the only reason I followed them as leaders and still consider them my mentors. It was their belief that we can, in the course of business, strive to help others, and also treat the empowerment of people as more important than our own positions of “power.”

The best leaders lead by example and inspiration, and not by force. Caroline worked within IBM to bring cloud technology, AI, and MI to bear for Stop the Traffik, a non-profit that tackles the crime of human trafficking in the world. Her teams followed her and were far more productive because they were inspired by Caroline and wanted to be a part of the work she was doing.

Throughout my career, I’ve been fortunate to have many mentors, sponsors, and role models in my professional life. It’s a valuable key to my success, and I encourage everyone to actively seek out these “human resources.” It’s also important to recognize that it’s a two-way street. You have to pay it forward and model the same behavior to newer colleagues that helped you when you started out.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

There are way too many to count! But, I’ll tell you about a book I read recently that really resonated. For this year’s “Growth Summit,” our annual sales conference, one of the keynotes was an interview I did with Leslie Odom, Jr., the Tony- and Grammy-winning star of Broadway’s Hamilton.

We talked about his book Failing Up, How to Take Risks, Aim Higher and Never Stop Learning. It seems like an unlikely topic for someone so accomplished to write about. But, through stories about his earlier career, he encourages us to embrace failure as not just a possibility but an opportunity.

And, I love the way he talks about life being a series of “graduations.” He wrote, “It’s not that learning stops once you toss up your graduation cap. Quite the contrary. That chapter of conventional and structured education may be over for you, but whatever your area of focus was in school, you’ll earn advanced degrees in Problem Solving, Team Building, Rebranding, Risk Assessment, Media Management, and many other subjects in life’s continuous course of study.”

The power skills he mentions are so important, arguably more important than ever as we’ve worked through a time of unprecedented disruption and change.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

That’s a great question — and one that’s near and dear to my heart. Like many leaders, I’m passionate about work, and part of that passion stems from believing in the purpose of the business. Over the years, I’ve made it a point to work for companies with solutions that truly benefit customers (and society), and with missions I believe in.

Skillsoft, which has been a true innovator in the corporate digital learning space, has a clear-cut belief, purpose, and vision. We believe every person has the potential to be amazing. Our purpose is to unleash human potential through learning. And, our vision is to be the most highly valued provider of learning solutions, preparing the workforce of today with the skills for tomorrow.

Skillsoft was built on a foundation of service leadership. Our products and solutions have evolved along with technology and world events. But, our commitment to service remains steadfast. We serve our customers at every level: individual, management, and organizational. We serve our Team Members by advancing a culture of leadership and learning. And we serve the greater community through partnerships with organizations like Special Olympics, the United Services Organizations (USO), Code Like a Girl, Talent Rise, and Ellevate Network, among others.

Are you working on any new, exciting projects now? How do you think that might help people?

Yes! I can think of two to share with you.

We’ve just released a new DEI curriculum, called “Diversity, Equity, and Inclusion In Action.” We’ve designed a series of courses to be impactful, inspirational, and experiential to help our customers advance, nurture, and sustain a culture that appreciates and champions DEI. With our experts, we learn the facts and demystify DEI concepts. Through real stories, told by real people (not actors), we inspire and empower each other. Through guided facilitation and discussion, we start to reflect and build new informed perspectives.

The other program that I’m excited about is designed to help mitigate what we call, “The Pink Pandemic.” Around the globe, COVID has disproportionately affected women. According to The Washington Post, the pandemic knocked 54 million women out of the workforce in 2020. And, while women account for only 39% of global employment, they suffered 54% of pandemic-related job losses worldwide.

Over the past year, Skillsoft has elevated the topic and created unique learning curricula that focus on how we can alleviate the effects of the Pink Pandemic. We published a 360 Report, developed a 5-part course called “The Pink Pandemic: A Recovery Plan for Women,” and added to our Aspire Journey: “Forging New Paths: Women’s Advancement in Life and Work.” We’re also sponsoring the EllevateHer Forward Fellowship program, a fund designed by the Ellevate Network to alleviate the economic burden of the pandemic on women and support their journey back to the workplace.

Thank you for all that. Let’s now turn to the main focus of our discussion about Digital Transformation. For the benefit of our readers, can you help explain what exactly Digital Transformation means? On a practical level what does it look like to engage in a Digital Transformation?

Technology has irrevocably changed the face of business. At the most basic level, Digital Transformation integrates technology into all areas of the business to effectively keep up in today’s ever-changing digital economy. To utilize digital technology to drive productivity, increase efficiency, and spur innovation — which is the number one business imperative for corporations around the world — every level of talent in the organization has to be digital-ready, not just the individuals in the IT function.

Which companies can most benefit from a Digital Transformation?

I would argue that there are very few companies that would not benefit from some level of Digital Transformation. And, there are some organizations that are truly reinventing themselves.

Ricoh, a customer of ours, is a great example.

Since 1936, Ricoh had been on the forefront of workplace innovation. Of course, in its early years, that meant introducing electric watches, office printing technology, and the first fax machine. They grew and evolved over the decades, offering IT and digital solutions to their customers, but still focused much energy on their core office printer/copier business.

By 2020, that core offering suffered as the pandemic forced offices around the globe to close. The company’s workload decreased putting its on-site print engineers in a tenuous position.

Ricoh was already in the process of transforming itself into a data-intensive IT services provider, having acquired a dozen digital companies. Rather than furlough their print engineers and hire new talent for their digital business, they cross-skilled and reskilled their current staff, filling the skills gap and building a pipeline of talent for the short- and long-term future.

By embracing Digital Transformation and taking advantage of the power of learning, Ricoh was able to adapt to the new — and the next — normal, truly making the most of their most valuable asset: their people.

We’d love to hear about your experiences helping others with Digital Transformation. In your experience, how has Digital Transformation helped improve operations, processes, and customer experiences? We’d love to hear some stories if possible.

At Skillsoft, our goal is to help individuals, leaders, and managers understand where technology provides the most value to the organization and how to leverage it. We help them become more knowledgeable about in-demand skill areas, like AI, Cyber, and Blockchain.

Organizations across all industries are facing the task of supporting the convergence of technical and business acumen. Trends include shorter product development cycles, “product-as-a-service” business model adoption, focus on customer success, big data and analytics as competitive differentiators, and deep collaboration via mission-based teams.

Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?

I think for many companies, the word “challenging” is an understatement. And that’s true around the globe. Let me share some numbers with you. In a study we conducted last year in the U.K., France, and Germany, only 22 percent of respondents said their organizations are fully prepared to provide the new skills required by digital transformation. But only half of the organizations in each country have increased investment in those skills.

Our curricula are designed to help customers identify the potential of technological innovations and determine the revenue-generating possibilities of pursuing them. We enable them to re-frame or extend traditional business models to include a stronger digital dimension. And, we help them better understand the range of ways that digital technologies can be leveraged internally to enhance communication and collaboration, increase innovation, and streamline operations, and improve the performance of individuals and teams.

Based on your experience and success, what are “Five Ways a Company Can Use Digital Transformation To Take It To The Next Level”? Please share a story or an example for each.

The benefits of Digital Transformation really come down to basic operational principles: efficiency and effectiveness. But there are many ways to use digital technology to help improve those two areas.

Digital Transformation can enable better collaboration. Digital solutions provide ways for both collocated and remote teams to partner on projects, share information, and improve outcome quality.

Digital Transformation can increase productivity through automation. Manufacturing and distribution can be streamlined through the introduction of robotics or other digital technology.

Digital Transformation can streamline internal operations. Time management, talent recruitment and development, financial functions, etc. can be performed in less time and with greater accuracy.

Digital Transformation can ensure consistency and best practices in project management. Digital tools can improve project planning, resource management, and contingency processes.

Digital Transformation can improve customer experience and satisfaction. Leveraging AI-driven data technology, companies can better anticipate customer preferences and needs, personalize interactions, and improve service.

In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?

One thing that we can all attest to is that disruption drives reinvention. Companies have been forced to innovate — and that’s a positive outcome of the past year and a half. At Skillsoft, we’ve rapidly created powerful new curricula to help our customers face the future. And, we’ve been inspired by some organizations that have used a time of uncertainty not just to survive or even to thrive, but to transform.

At Skillsoft, we refer to it as building a “culture of learning,” one in which everyone is given the opportunity to acquire new skills and knowledge. This means focusing on accessibility for all. If two-thirds of your workforce is behind the wheel making deliveries each day, you have to provide access to learning via remote channels and during off hours.

A culture of learning and innovation has to be promoted, supported, and modelled at every level of the organization. It can’t just be an adjunct of HR. And, the rewards for the organization are just as rich as the rewards for the individual. When the employee experience improves, employee satisfaction, retention, and productivity improve as well.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I’m a firm believer that the best outcomes happen when you see the connection between and embrace both the personal and professional. I try to — and encourage my team to — participate as, nurture, and reward the whole person. So, one of my favorite professional quotes is actually from one of my personal heroes: singer/songwriter/author/producer/humanitarian Dolly Parton.

“If your actions create a legacy that inspires others to dream more, learn more, do more, and become more, then, you are an excellent leader.”

This is what I strive for, whether I’m leading a small team or hundreds of people around the globe. And, I’m so fortunate to work for Skillsoft, an organization that is, quite literally, in the business of helping people dream more, learn more, do more, and become more.

How can our readers further follow your work?

There are a couple of ways. On my website, michellebb.com, I write a regular blog dedicated to the intersection of life and work. Writing is a wonderful tool for self-reflection and for making sense of a world that has turned upside down. It’s also a powerful way to connect to others — especially at a time when we all feel so disconnected. The most personal stories I’ve shared have also generated the most feedback, with readers reaching out to share their own version of my experience.

And, I also host a biweekly podcast series called, “The Edge,” a platform designed to help leaders and learners alike unleash their edge. In the series, now in its second season, I sit down with a variety of quests — from customers, to partners, to industry influencers — to engage in candid, thought-provoking conversations on the topic of learning and growth in the workplace. It’s available on Apple Podcasts, Google Play, and Spotify, or through Skillsoft’s website.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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