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Future Proof: An Upskilling Primer

Retail workers at Goodwill San Antonio.


As part of our “Future Proof” series, we’re covering the future of work landscape and the tools, pathways, and trends for designing educational programs that equip learners for an evolving workforce—past issues covered skills mapping and 21st century skills curriculum mapping as key tools. In this “Future Proof” spotlight, the Lab’s education designer Isaac Agbeshie-Noye provides a primer on upskilling, a human capital trend, and shares examples in practice and lessons learned to date from our upskilling initiative in San Antonio, Texas.


Here’s a primer:

What is upskilling? 

Upskilling is the practice of teaching current employees new skills that prepare them for more advanced responsibilities in the workplace. 

What is an example of upskilling? 

Upskilling looks different depending on the organization—think an education benefit, an apprenticeship program, or professional development that aims to retrain or re-tool employer capacity. Regardless of its form, an upskilling practice (or program) is an opportunity for employees, particularly those in low-skill or entry-level positions, to develop skills that will take their careers to the next level. 

Upskilling isn’t new. Many large-scale, for-profit companies have designed internal practices of upskilling to keep their business, and their workforce, competitive. AT&T’s Future Ready establishes and embeds professional training to equip employees with the skills needed for a set of jobs identified as key for the future of the company. Another, Amazon’s CareerChoice program covers tuition and fees for employees pursuing degrees in growth industries (such as transportation, healthcare, mechanical and skilled trades, or computer science and information technology) and provides a pathway to connect employees with employers in need of talent. 

How does upskilling fit into the future of work?

The future of work presents a new landscape:  40% of US  jobs are predicted to be lost to automation over the next 15 years, digital and tech-enabled services are on the rise, and 21st century skills (also known as “soft skills”) are and will become the most critical. 

Upskilling has become a key human capital strategy to proactively prepare current workers for the evolving digital economy. From an operational standpoint, the value is clear. Companies can take an active role in training up staff to assume open roles without investing as much in recruiting / onboarding new talent; professional development programs lead to increased retention and employee satisfaction; and such training programs can better position companies to be more attractive and competitive in the marketplace.


What is the benefit to partnerships between higher ed institutions and employers looking to upskill their workforce? 

Upskilling does not have to pit higher ed against employers. Instead, upskilling provides a rich opportunity for the two sectors to partner. Employers still heavily rely on colleges and universities to produce graduates that can fill open jobs. As education providers, colleges and universities can work in close partnership with employers to provide upskilling opportunities to incumbent workers, particularly with businesses that cannot afford to run their own upskilling programs. We have seen some large examples of this: Starbucks with Arizona State University or Chipotle with Guild Education, to name a couple.


At the Lab, we believe that investment in upskilling can lead to stronger local economies, reduced income gaps, and a more nimble workforce. 

We are on the ground working with Goodwill San Antonio, Alamo Colleges District, and San Antonio Works, with support from Walmart, to design and build a talent pipeline for fast-growing middle-skill jobs in San Antonio, Texas. Our target population, Goodwill “team members” (or employees) are largely adult learners (over age 25) that have completed high school or earned a GED, are highly motivated in furthering their education, and are mostly working in retail services. The goal? Build opportunities for incumbent frontline retail workers to develop 21st century skills in order to advance their careers, and, ultimately, create a scalable model for a non-profit upskilling program that partners local education institutions with big regional employers.

Currently in San Antonio, we are piloting two pathways to upskilling featuring the Lab’s 21st Century Skills Badges: Skillsbooster, a 21st Century Skills Badge bundle, and Certificate Plus, a certificate pathway with a Badge embedded into the introductory course. Both pilots aim to provide incumbent workers the necessary skills to ascend into advanced roles. Testing these programs with Goodwill’s frontline retail workers allows us to learn from and design for a population that is in danger of being left behind in a rapidly-changing knowledge economy. 


Here are three things that we have learned in our work thus far:

1. The barriers to upskilling are just as important as the upskilling pathway itself
An upskilling program is only as good as one’s ability to access and fully engage with it. Upskilling efforts have the potential to fall flat if employers are not intentional about ensuring that everyone has access to them.

In San Antonio, we worked closely with Goodwill San Antonio to identify and understand fundamental barriers that had prevented employees from participating in prior upskilling programs. While an online learning experience is the most accessible approach for employees, we have learned that it can also create an additional barrier for learners who are unfamiliar with using computers or navigating online environments.

Access to financial resources also continue to be a barrier for employees looking to upskill. Many employers feature tuition reimbursement programs that incentivize degree and credential completion, but finances become a barrier for those who cannot afford to make the initial investment in their education and/or who don’t qualify for federal financial aid. Goodwill San Antonio realized this and evolved their current tuition reimbursement policy into a “last dollar match” program. Through a third-party billing relationship established directly with Palo Alto College, the organization is able to cover the remaining tuition costs for the certificate program after financial aid has been awarded.

Employers of low-skill workers should consider both building in digital literacy training and financial supports as pathways to upskilling.

2. Collect data early and often to justify the upskilling investment
Many have tried to quantify the return on investment for upskilling initiatives. Recently, in a Lumina Foundation study, Cigna saw a 129% return on investment in upskilling efforts around education benefits. In order to best understand how upskilling is benefiting a company, employers need to invest in their capacity to track and measure employee development and performance. In collaborating with Goodwill San Antonio, our design process unearthed a host of questions related to outcomes and success metrics. As a result, we have learned about performance indicators that are important to capture to understand how the program is advancing Goodwill’s mission to “change lives through the power of work.By leveraging demographic information, program satisfaction data, and other measures, such as program completion, job performance, and employee retention, an employer will be able to determine which interventions are most effective for their team members, as well as create more pathways for talent to transition into middle-skill roles.

3. It takes a village
In a mission-oriented organization like Goodwill San Antonio, the ongoing professional development of employees is a top priority. As a result, managers and senior leaders all needed to buy into an upskilling strategy. In order to position frontline retail workers to take advantage of upskilling programs, Goodwill San Antonio underwent a transition—moving their Talent and Development department, which oversees professional development, out of Human Resources and into its Mission Services division. The result? Upskilling became a strategic goal by which the organization will measure its impact in the coming year. With increased attention paid to training and development, Goodwill employees on all levels have a shared understanding that the time spent learning new skills in a classroom (or online) is just as important to production goals as their time working on the floor.While senior leaders set vision and allocate resources for employees to upskill, managers have a key role in recommending participants, assessing performance, and helping employees to make connections between the course content and real work situations. This “all hands on deck” approach normalizes upskilling across the organization and creates a culture of care that supports frontline workers.

For upskilling programs to be truly successful as the global work landscape shifts, they must be designed with the needs and experiences of both the employee population at-hand and the organization itself in mind.

Interested in learning more? Explore upskilling and its role in the future of work at:

To learn more about UpSkill SA!, visit our project page