An interview with CMO of Skillsoft, Michelle Boockoff-Bajdek

1. Why did you end up leaving IBM Watson?

It wasn’t an easy decision. I spent almost five years at IBM as the result of the acquisition of The Weather Company (The Weather Channel), and had the opportunity to serve most recently as the CMO of IBM Watson, responsible for a portfolio of products that leverage artificial intelligence to help businesses make better decisions. I was also responsible for the company’s overall positioning of AI and served as the steward and shepherd of the Watson brand. It was an exceptional organisation, and I couldn’t be prouder of my accomplishments and the people I had the privilege of working with.
It took a very special opportunity to convince me to leave — and that’s what they offered me at Skillsoft.

2. What drew you into Skillsoft the most?

I’ve always been fascinated by the impact technology has on our daily lives, both at work and at home. And learning has been a common theme throughout my career. At Skillsoft, I have the opportunity to focus on the perfect combination of both: helping people grow and thrive through the use of digital learning technologies. I decided long ago that I would only work for organisations that are striving for — and achieving — good in this world. A company’s purpose and mission are equally as important to me as the products and/or services they sell.

At Skillsoft, we believe every person has the potential to be amazing. We deliver online learning, training and talent solutions that help organisations unlock the potential in their most important assets: their people. We empower 36 million learners around the world, helping them build the skills they need to succeed, and organisations build the teams they need to stay ahead in a rapidly changing world.

3. Did you have a plan of what you wanted to accomplish? A 30-60-90 day plan for example? 

Yes, I did. But, it’s 2020; I doubt I’m the only CMO who had to rethink her plans. One of my most important undertakings when I started at Skillsoft was to launch a new brand for the company — one that was driven by a deeper understanding of our customers, their needs, and their goals. It was a major shift for us, redefining what we really offer… not courses, certifications and badges, but the opportunity for every learner in every organisation to reach their greatest potential, to ‘unleash their edge.’ I also needed to build a team from the ground up that could truly drive the business, but also could adapt to market signals effectively. It is for that very reason that we adopted agile and apply it to everything that we do.

4. What challenges have you had to overcome with Covid-19 and remote working in place? 

I’d been the CMO at Skillsoft for approximately six months, and the most important initiative on my list was Perspectives, our annual user conference. It was to be a thoughtful and high-end, but fairly conventional, event: with live programs in Florida, London, and India. And we had lofty goals to increase participation by 25% to more than 1,200 attendees – aggressive but achievable.

Then everything changed.

The first week of March, we realised that planning a live destination event was impossible. But, we took the opportunity to shift our thinking entirely and reimagine what a digital experience could be. We spent 28 hours over two days in a design thinking workshop, including members of our customer communities to determine what they wanted from a modern digital experience. We also looked at examples of companies that have held successful live experiences across industries — from Peloton, to Apple, and even The Bachelor. It was an exercise in being agile and creating something entirely new out of a less-than-ideal situation. And we recognised that we had an opportunity to turn this limited, in-person regional event into a global day of learning for everyone.

Perspectives became a free, 24-hour, online experience, starting in Sydney, Australia, and wrapping up in San Francisco, California. We featured more than 100 speakers in keynotes, case studies and head-to-head debates. There were product demos and regional business continuity panels. There were music and yoga breaks, and ample opportunities to ask questions, suggest solutions and participate in what turned into a 24-hour conversation about everything from personal development to diversity and inclusion training; from leading in challenging times to lively discussions on who owns the skilling agenda. By transforming Perspectives 2020, we were able to live our mission by democratising learning, making it available and accessible to all of our 40,000 registrants.

The single biggest takeaway for me was that this was not just about teaching people new skills; it was about improving our collective well-being — developing the whole person. If there’s anything Covid has shown us, it’s that the line between the personal and professional is — and should be — flexible. When we continue to learn and grow and achieve, it benefits our work life and our home life.

This is the theme that’s surfaced in all I’ve accomplished so far at Skillsoft: the idea of holistic learning. This is precisely who we are and what we do.

5. What’s been the most rewarding part of your job so far?

There’ve been so many. I think overall, it’s been the opportunities I’ve had to address our customers’ very real needs in real time – this idea of ‘sensing and responding.’ For example, as a result of the coronavirus pandemic, businesses had to transition to remote working and virtual teams; digitally transforming themselves almost overnight.  We thought about what managers and workers needed and built a Business Continuity Center with learning content, handbooks, and checklists. A couple of months later, when the Black Lives Matter movement re-emerged, we put together a Diversity, Equity, and Inclusion (DEI) programme with live Leader camps, reports, podcasts, and videos to help leaders at all levels drive meaningful change within their organisations.

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