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5 Questions With Steve Lee of SkillUp

The Cutting Ed
  • January 28, 2026
Meghan Whittaker

At a moment when more than half of the U.S. workforce is skilled through alternative pathways, short-term training and nondegree credentials are increasingly central to economic mobility. Yet, the systems meant to support these pathways remain fragmented and uneven in quality. Steve Lee is the CEO of SkillUp, a nonprofit that helps people without college degrees connect to high-opportunity jobs, quality training, and supportive employers, reaching millions of users through a national platform and regional sites. In this 5 Questions interview, Lee reflects on what workers actually need from career navigation, why participant voice matters, and how technology and human guidance can work together to expand access to meaningful careers.

What is the nature of your work?

Steve Lee
Steve Lee

SkillUp is a non-profit that helps individuals without college degrees secure high-opportunity, in-demand jobs. SkillUp acts as a concierge career navigation service, connecting those looking for a better career to training programs and employers and systems looking to hire or support job seekers. We have served over 4 million users through our national platform or one of 49 regional sites.

At SkillUp, we aim to rewire the fragmented career navigation process and improve impact through an integrated, AI-powered navigation system for low-income job seekers. By coordinating and optimizing multiple AI tools, data sources, and workflows from trusted nonprofit organizations, we will create a single, seamless experience for users that addresses multiple barriers to economic mobility.

With acceptance into Google’s AI Accelerator program, we are positioned to revolutionize workforce development for underserved populations.

Why is this work important?

More than 50 percent of the American workforce is skilled through alternative pathways. Short-term training opportunities – and the careers they lead to – have become some of the most prominent alternative pathways for this fast-growing population. In the first decade of the millennium, the number of short-term certificates awarded by community colleges increased by more than 150 percent across the United States. 

Although supply and demand for short-term training also continue to rise, we have no centralized system for collecting basic training program information or outcome data. Additionally, the continued need for short-term training has resulted in a flood of programming that does not always benefit the student. According to a New America study, certificates related to specific occupations see positive labor-market value while others show no or even negative impact. This leaves workers with few credible tools to support their short-term training journey. At SkillUp, we understand we can only achieve our goal of supporting individuals to obtain quality employment with in-depth research and quality standards to ensure what we promote to job seekers truly has a positive ROI. Each of our catalogs is built with this balance in mind – cutting straight to the highest value, lowest barrier programming for our users.

What’s been the biggest surprise so far?

I’ve always believed that those closest to the problem are closest to the solution. The power of participant voice is crucial for the work we do. Given this, an “ah-ha” moment for me has been this notion that career navigation may not be what many of SkillUp users want. Some do, of course. But for many others, what they really need is a guiding hand on their journey, someone who will help them “doubt their own self-doubt.” It’s why SkillUp’s group coaching services have proven so popular, because it gives users guidance on specific topics important to them, to help them “doubt their own self-doubt.” 

I’ve also been struck by the notion that many of SkillUp’s users want a career, but still feel as if college is the only way to that. But given that, and the fact that many users need income now, they choose to forego college to take suboptimal jobs with no career possibilities. It’s a vicious cycle. It’s why “Earn and Learn” opportunities offer so much possibility for the population that we care about. It’s why we are excited about our “Earn and Learn” platform that connects workers to such opportunities in a simple, streamlined process.

Where do you see your work in five years?

Given the complex, multi-step journey from career discovery to employment – with each step presenting potential dropout points – in five years, we aim to rewire the fragmented career navigation process and improve impact through an integrated, AI-powered navigation system for low-income job seekers via an intelligent orchestrator. 

We plan to have an “AI Financial Supervitamin,” a multi-agent technical infrastructure that allows domain experts to integrate specialized services into one comprehensive, AI-powered experience. When a user poses a query, the orchestrator analyzes the user’s need, dynamically assigns a “main” agent and “supporting” agents, and facilitates an iterative workflow of collaboration, reflection, and memory updates to synthesize a single, comprehensive response to the job seekers’ needs. While each single point solution is powerful alone, we believe the true potential is realized through a collaborative approach that outperforms the sum of the specialized, single point solutions. The platform will deploy multimodal coaching through voice conversations and text-based support, and relationship building that maintains conversation history and provides proactive guidance over time.

What else should people know?

We have big ambitions for the next five years, and our North Star goals for SkillUp 2030 are:

  • 10 million: Users served
  • 1 million: Jobs secured
  • $500 billion: Lifetime earnings

To accomplish this, we’ve anchored on three core priorities:

  • Regionally Focused. Economic mobility happens at the local level. We’re currently in 35 regions across the country, including the top 30 MSAs. The goal is to be in every state, in the top 100 MSAs.
  • Technology Forward. We focus on three fronts. First, to be the source of trusted, high-quality information and personalized product experiences for STARs. Second, by acting as “data agent”by “importing” data sets (e.g., American Opportunity Index and Credential Values Index) to signal quality to SkillUp users; and “exporting” SkillUp’s data sets to partner organizations to power their technology platforms. And third, of course, AI, specifically evolving human-centric web into Agentic AI-centric web through MCP and Agent2Agent protocols, and connecting to different data points via an intelligent orchestrator.
  • Partnership Enabled. Our official name is SkillUp Coalition. Through coaching, on-the-ground partnerships, and purpose-driven community, we’ll drive meaningful human connection to drive enhanced engagement, scale and growth.

Meghan Whittaker

Program Director

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