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We’re passionate about the world of work, and how we can make it better. To help satisfy our curiosity, we’ve launched an interview series where we pick the brains of experienced leaders, business owners, managers, and individual contributors to get their thoughts on how we can collectively build better workplaces.

Charlie Schilling

Charlie Schilling

Join us in our next installment below as Charlie Schilling—President, Enterprise Business at Emeritus—shares his insights with us.

We’d love to get to know you a bit better, tell us a bit about your backstory.

My professional background begins with ice cream: once I had my driver’s license as a teenager, I drove a Good Humor Ice Cream truck. Much to my seven-year-old daughter’s disappointment, however, I did eventually have to give up the keys, and ultimately pursued a career building businesses around empowering people through education.

Today, I lead the US, Europe & Canada Enterprise business for Emeritus, a global education leader committed to teaching the skills of the future to individuals, companies, and governments around the world.

And education has been a throughline in my career: after early days as an investment banker focused on technology, media, and telecom, I was General Manager of Corporate Markets at GLG, a member of the CEO’s Office at Bloomberg LP, and a consultant at the Boston Consulting Group. This all led me to the executive team at General Assembly, leading our enterprise business, which focused on teaching entrepreneurs and business professionals practical technology skills. I see education as key to the future of work.

If we were to ask a friend to describe your personality to us, what would they say?

It depends on which friend you ask, I suppose! On balance, I imagine they would say that I am high energy, both in and outside of the office. I thrive being around others in groups large and small. 

Thinking back to your career journey, what’s an interesting story that stands out?

When I was in college at Georgetown, I worked on Capitol Hill, which was an amazing experience. I did lots of things like opening letters and helping to maintain one of the first email systems used by a US Senator. The best part of my job was occasionally getting asked to pick the senator up at Dulles Airport in his GM Geo Metro. These drives were amazing. From my perspective, the more traffic the better— it was a chance to ask questions and learn. Today, I think about this all the time, and it’s true for leaders at all levels:

always approach with curiosity, and seek out opportunities to learn.

What’s the most impactful lesson you've learned over your career thus far?

Early in my career, I worked for a mentor who had an incredible approach to solving problems, structuring work, and building trust. When a new assignment would come up, their approach was, “ok, this is what our client needs to do, and here is the context. I am going to get started by doing x,y, and z. What I need you (and the rest of the team) to do is a, b, and c.” What I learned from this approach is that it’s important to share context and show that you are all in it together, with the boss willing to also roll up their sleeves.

This type of servant leadership is incredibly important, where everyone has the opportunity to grow and contribute towards an ambitious vision, and it’s always grounded in empathy.

Thanks for giving us some insight into who you are! Let’s jump into things. When you hear the phrase “build a better world of work”, what comes to mind?

To me, this phrase means building a world of work that includes and respects individuals, and gives them the room to be themselves and explore their passions, all while moving the ball forward for the company. Perhaps not all the time, but work should be joyful and provide a sense of accomplishment.

If you aren’t laughing at work and with your colleagues for at least some of each day, it’s probably time to find something new.

For you, what’s the main blocker you see as standing in the way of building a better world of work?

The main blocker is education. Too many people do not have the skills they need to compete in the workforce, and most companies are ill-equipped to provide learning paths that will help current and future employees succeed. At the same time, people in many regions around the world are priced out of education, which means that skill gaps only expand. Part of what gets me excited about my work is the opportunity to help companies think about how this can be done differently, providing benefits to employees and employers alike. 

What’s one thing within our control that we can practically do to build a better world of work today? And, how do you recommend going about it?

The main driver in building a better world of work is fostering and encouraging employees to embrace lifelong learning and giving them practical, fulfilling reasons to stay with their current company. 

In some quarters of the world of work, particularly with the emergence of remote work and distributed teams, it’s too easy for people to feel isolated and culture to fall apart, or to feel like their work is not contributing or having deeper meaning; that’s when people quickly switch to the next shiny thing. Proactive employers who invest in building and empowering talent will build a better world of work.

At a societal level, we need to build the right conditions. Unfortunately, today the US limit for employers to contribute to employees’ education assistance programs is too low: it’s about $5,000, when realistically it should be closer to $13,000. While the Biden administration has now taken steps to relieve student debt and payments because of the pandemic, it’s now time to take that a step further and shift more of the burden of continuing education payments to employers.

Charlie Schilling interview quote graphic

At the same time, HR and L&D teams can also push for their organizations to take on educational costs, to help make lifelong learning more accessible for all. Studies show significant benefits when organizations roll out successful tuition reimbursement programs: they can better retain and attract talent, increase organizational readiness for the future, and build competitive advantage to stand out in today’s talent war.

By investing in your people now, you’ll help them grow internally, and you’ll see immediate ROI for your business when your team is upskilled and reskilled.

Can you share one thing you’ve experienced, seen, or read about that is leading us towards a better world of work?

Making the workforce more diverse and inclusive is building a better world of work, no question! As the husband to a female CEO and father to two daughters, I am so happy to see more women in leadership roles, and a growing culture of more balance between work and family obligations. We still have a long way to go, but we can all be part of building a better, more inclusive world of work.

As leaders, we have a responsibility to shape policies so that everyone has an equal opportunity to succeed. At Emeritus, we’re always looking for ways to build more inclusive policies, and we recently replaced a limited maternity leave policy with an inclusive parental leave policy, available to all employees. Evaluating policies, getting feedback from your team, and making updates to be more inclusive will benefit everyone.

I’m curious, thinking about building a better world of work. Is there a company and/or leader who stands out to you as someone we should follow? If so, what are they up to?

I am biased because I used to work there, but the company I admire most is Bloomberg and its leader Michael Bloomberg. The company’s products are incredibly useful in the markets it serves. Uniquely, the company and its leadership unabashedly support causes integral to creating a better world of work, like education, climate change, and public health. 

How can our readers follow your work?

You can follow me on LinkedIn and Emeritus on LinkedIn and Twitter for all of our latest news and events with university partners.

Thank you for adding your voice to the People Managing People's interview series on How to Build a Better World of Work!

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Tim Reitsma
By Tim Reitsma

Tim has deep experience in HR, people & culture, leadership, business strategy and operations with a focus on building great teams who are excited about their craft and their organization. With over 15 years of leadership experience, Tim has always been guided by his core values: faith, family, curiosity, and fun. He is a coach, mentor, speaker, advisor, and an active volunteer in his community. Tim loves spending time outdoors with his wife and two kids as well as mountain biking in the north shore mountains.