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Doubling Down on Upskilling—A Roundtable Discussion on Effective Strategies in a Volatile Marketplace

Meet the pundits

Eric Jones, SF ’05: Headquartered in Washington, DC, U.S. Coast Guard Rear Admiral Eric Jones is the Deputy for Personnel Readiness in the office of the Deputy Commandant for Mission Support. He oversees the recruitment, development, and support of the Coast Guard’s diverse workforce—nearly 90,000 active-duty, reserve, civilian, and auxiliary personnel.

Jurie Strydom, SF ’11: As CEO of Sanlam Personal Finance, the retail arm of one of the largest financial services groups in Africa, Jurie Strydom oversaw 12,000 people across the full financial services value chain from advice to investments. Jurie was previously the chief executive of Regent Insurance Group. He is now a fintech advisor and investor.

Sofia Theororidou, SF ’17: A Fortune 500 financial services executive, Sofia Theororidou is Chief of Staff to the Chief of Operations and Human Resources Officer at Edelman Financial Engines. Previously, she served as Senior Vice President and Global Chief Administrative Officer for Alternative Investment Solutions at State Street. Sofia also has advised startups on financial planning and commercialization strategies.

Jeff Williamson, SF ’12: Jeff Williamson describes himself as a people-first senior executive with 20 years of diverse logistics, operations, human resources, labor relations, marketing, finance, and business analytics experience in both the public and private sectors. Before his role as Vice President, Human Resources Excellence & Strategy at Booz Allen Hamilton, Jeff was Chief Human Resources Officer and Executive Vice President at the United States Postal Service.


Skill development—or upskilling—programs have evolved dramatically in just the last few years. What works, what doesn’t?

Jeff Williamson, SF ’12

Jeff: At Booz Allen Hamilton, we ask every employee, “What do you want to do?” Then we look at what skill gaps are keeping them from making that next move. Sometimes, they’ll have their sights set on working with a particular client, so we help them figure out the capabilities they will need to qualify for work with that client. We want them to think boldly and broadly on how they might expand their perspectives and their abilities. Also, we’ve launched employee-led technical experience groups so that employees can mentor and be mentored within a particular professional area. And we’ve embedded DEI into every training program rather than as an insulated initiative. It should be a part of our approach to everything we do.

Sofia: Most large global financial services organizations have an overarching training strategy for all employees that concentrates on the skills common to all functions and business units. Human resources usually oversees the planning and development of that kind of training. Then there are separate decentralized training programs organized at the business-unit level that are often technical in nature and address job-specific skills. Many companies rely on third-party providers for content that changes rapidly yet addresses an urgent need, like compliance trainings around regulatory requirements in banking and capital markets.

Jurie: We, too, often rely on outside vendors to stay up to date on many issues like regulatory requirements and the latest technologies and best practices. We don’t want to have to focus on generating knowledge in fields where there are others better placed to do so. We turn to the innovators working on the frontier of cybersecurity, for example, to keep us current on issues that are highly relevant to our business but are not our business. Happily, there are outside experts at universities and private consulting firms dedicated to that.

Eric: Especially when it comes to technology, we need to rely on outside experts. Ninety percent of the commerce that flows into the United States flows in by sea. As we have seen during the pandemic, kinks in the supply chain can have a powerful impact on the economy, and supply chains rely heavily on technology. Coast Guard vessels are part of that supply chain. Our staff—enlisted and civilian—must stay up to date on navigation, high-frequency radio, and cybersecurity technologies. They must be able to communicate with trucks and rail systems to keep goods flowing. We also want our people to develop a more global perspective about their personal role and the role of the Coast Guard in the wider world. For this level of training, we look to the experts in both technology and leadership at institutions like MIT Sloan or Harvard Business School. They are devoting all their resources to staying at the leading edge, so we know that our people will benefit from the latest crucial knowledge.

Technology now dominates most upskilling programs. What are the pros and cons of the growing reliance on digital tools?

Jurie Strydom, SF '11

Jurie: Online courses allow employees to follow the material at their own pace and to re-do lessons they aren’t clear about the first time around. Online programs test the person taking the course without fear or favor, giving a clear, unbiased assessment of the test-taker’s knowledge. You either know the material or you don’t. The subjectivity inherent in assigning grades is removed. There’s an equitable quality to online training—you can participate no matter where in the world you happen to be. And it allows us to effectively and economically train 100 people, where in the past we’d have to choose 10 because of the cost and disruption of sending employees to an in-person program in another city or country.

That said, elements of in-person learning are essential in some areas—executive leadership training, for example. Leaders must get out of their comfort zones and immerse themselves in an environment where they are exposed to and inspired by new ideas, new people, new ways of looking at the world. I have always made a point of withdrawing from the workplace every six or seven years for several months to do something worthwhile like travel or, as I did a while back, spend a year at MIT in the Sloan Fellows Program. You need periods of “away” to see challenges from a richer perspective.

Eric: It all depends on who is learning and what they’re learning. We have four types of employees in the Coast Guard: 43,000+ active-duty military, 8,000 reservists, 20,000 members of the Coast Guard Auxiliary, and 10,000 civilians, so management and training must embrace every avenue of learning to suit the job and the person learning it. We do offer online programs, but we also have many hands-on programs for jobs like technicians and boat drivers. Most important, we avoid creating a monolithic culture that is not open to the latest thinking being generated out in the world, so we send our people off to work with global experts in fields like cybersecurity, human resources, management, or financial analysis. The Coast Guard sent me to Brown University to get a degree in math, then to the MIT Sloan Fellows Program to learn to manage within such a complex environment.

Jeff: Our talent system is powered by people who’ve earned many of their skills through online training. We have 29,000 employees and rely on technology to promote and advance people on pathways that help them thrive. Technology makes education more accessible to everyone. But people learn in different ways, and we are super attuned to the delivery of knowledge. We rely on microlearning, podcasts, videos, self-paced courses, crowd-sourced knowledge—and in-person learning experiences where in-person interaction is important. We want each employee to achieve their goals. When they do that, we achieve ours. We are building a broader, deeper talent pool. It’s smart, it’s strategic, and it’s philanthropic. Technology is a key tool in that mission.

Sofia: Technology has enabled a virtual or hybrid training environment and a move away from in-person trainings that were difficult and expensive to scale. With self-paced and personalized online study, more people can learn more skills. It’s faster and easier for teachers and learners to continually update knowledge. If there’s a disadvantage, it’s that some employees may feel isolated and miss the interaction of the physical classroom, or they may have screen fatigue—especially in the Zoom era. The pandemic has, of course, only accelerated the role of technology in upskilling.

So, let’s talk about the tech ramifications of the pandemic—remote work, for example.

Sofia Theororidou, SF ’18

Sofia Theororidou, SF ’17

Sofia: Financial sector employees are relatively tech savvy because staying current with the latest technology is part of the job, so they were fairly comfortable going remote when the pandemic hit. Most companies in this realm had introduced work-from-home programs long before the pandemic and were used to various workplace scenarios—in the office, fully remote, or hybrid. Post pandemic, though, we've seen companies stepping up their investment in their technology infrastructure and work-from-home support systems. Many have done a great job at communicating their technology suite (hardware and software) and enhancing tools to digitize workflows, enable connectivity, and improve self-service capabilities in support of flexible work.

Jeff: We never stopped going to work, even though most of us were working from home. In fact, we actually increased our headcount. During the early stages of the pandemic, we deployed $100MM to support employees in various ways such as enhanced dependent care benefits, additional leave options, and remote work equipment and setup. We wanted employees to know we were supporting them just as much in a virtual work environment as we did when they came into the office every day. And because we have so many technology tools, most upskilling programs could go on without a hitch.

Jurie: The pandemic had the unexpected effect of upskilling many people in terms of computer skills. People who would never have dreamed of mastering Zoom were exploring its many features and sharing this new knowledge with colleagues. Maybe it was how to insert the Eiffel Tower as your meeting backdrop, but these somewhat silly virtual forays actually served to give many employees a fresh confidence about using software tools. I am concerned, though, that we need new upskilling programs around remote and digital work. What is the most effective way to manage a remote workforce? What are the best ways to collaborate? How should remote employees be held accountable for their output? What is the acceptable extent of flexibility? These questions raise other questions. How to be a responsible employee and a responsible manager in a virtual workforce, for example. Even more challenging, how do you effectively manage and collaborate in a hybrid workforce where some people are in the office and others are remote? Upskilling programs need to respond to these issues immediately.

Eric: The Coast Guard is not an intuitive work-from-home organization. But since the pandemic, more and more of our workforce wants to be able to work remotely. Unfortunately, at least at the moment, you can’t pilot a boat patrolling the waters off Miami from your home office in Tulsa. We’re expanding the options for those working in desk jobs, but the lack of options to work virtually is definitely a retention issue for us as other types of employers are offering more and more flexible options.

Which brings us to the issue of retention. If you would, share one last thought about upskilling as a recruitment and retention tool.  

Jurie: It’s a huge differentiator. All major companies provide “basic training,” but a company today has to show that it offers something broader within an employee’s professional box—and not just access to online learning. Any employer can do that, and employees can access a lot of online learning without the company’s support. A company that wants to attract and retain employees will offer access to other types of learning that are not tied specifically to their job description so that they have the opportunity to broaden their skills. It’s important, with young people in particular, to give them plenty of opportunities to learn to socialize within a work environment and to hear the interesting—and edifying—conversations among senior employees in the same role.

Eric Jones, SF '05

Eric: While our retention is higher than the other services, we do have both attraction and retention challenges because we don’t have as much control over salaries as private companies do. Also, owing to the work we do, we are not able to offer the same kinds of flexibility. We try to make up for any liabilities with excellent upskilling opportunities. We have a powerful upskilling trajectory in place for enlisted personnel, and we are working to make sure civilian employees have attractive options for growth as well. We always are focused on the leading-edge, and employees know that we will be giving them high-quality training that makes them competitive beyond the Coast Guard. Leadership training, for example, is widely available, whether you are a boat operator or a machinist or a financial analyst. 

Sofia: Workplace skill development programs are a huge strategic differentiator in a knowledge-based economy, and the financial services sector is no exception. Employee engagement surveys validate this year after year. Employees, regardless of demographic profile, rate the need for learning and development, upskilling, and on the job training very high, so upskilling initiatives, when well-advertised, play a huge role in attracting talent. Prospects look for positions that will help them attain professional certifications that increase employability, such as CFA, CPA or FINRA series. Entry-level associates look for programs that offer course-based and structured on-the-job training. The quality of your upskilling offerings becomes part of a company’s brand and ethos. It’s never been so important.

Jeff: It used to be that we thought of attraction and retention as two different initiatives. Now, we see them as an integrated effort. Upskilling is a deep-rooted mission in our organization. If we give our people the chance to grow in every direction, our organization thrives, too. Applicants can see the span of these efforts, and our current employees spread the word in the employment marketplace. There are so many reasons to do the right thing—some of them are strategic and some of them are philanthropic—but they all lead to the same outcome. Success for all involved.

For more info Mike Miccoli Associate Director, Marketing (617) 324-8101