AI Reskilling + Upskilling: The Billion-Dollar Opportunity Hidden in Workforce Disruption

Reskilling in the age of AI is no longer a nice-to-have; it is an urgent strategic advantage. As artificial intelligence reshapes industries, millions of roles are evolving or disappearing entirely, creating both a challenge and an unprecedented opportunity. 

George Bandarian emphasizes, “What we’re really looking for are founders who are leveraging these tools and have a bunch of agents on their team” 

Businesses that embrace reskilling and upskilling programs can unlock massive productivity gains, retain top talent, and position themselves as leaders in the AI era.

The good news? Organizations that pivot quickly are seeing measurable benefits: higher employee satisfaction, better retention, and a clear path to long-term growth. 

Untapped Ventures is actively backing founders who understand this shift, building solutions that empower both employees and enterprises to thrive alongside AI.

Let’s learn more about AI Reskilling.

Why Reskilling in the Age of AI Matters

The workforce is changing faster than ever. McKinsey reports that by 2030, up to 375 million workers globally may need to switch occupational categories or acquire new skills to remain relevant. That’s roughly one in every ten employees worldwide. Does it not sound insane? 

Bandarian notes, “Software used to help a human deliver a service, now the software is the expert and delivers the service”, underlining how AI is transforming work from augmentation to collaboration.

AI technologies are automating repetitive, rule-based tasks across sectors like finance, healthcare, and customer service. But automation is not about replacing people. Moreover, it is about transforming their roles and enabling employees to focus on higher-value work.

Key drivers for AI Reskilling include:

• Skill Gaps Are Growing: Roles in AI, data analytics, and automation are expanding rapidly while the supply of trained talent lags behind.

• Employee Retention: Workers are more likely to stay in organizations that invest in their development. LinkedIn found that 94% of employees would stay longer at a company that invested in their learning.

• Future-Proofing Businesses: Companies that proactively reskill employees can adapt to market shifts faster than competitors.

For example, AT&T invested over $1 billion in employee training programs to equip staff with AI and cloud computing skills. This proactive strategy not only increased internal mobility but also boosted employee engagement scores by 15% in three years.

From Upskilling to Strategic Transformation

Upskilling is not just about learning a new tool or software; it is about creating a culture where employees can continuously evolve alongside AI technologies. 

Bandarian observes, “With Agentic AI, we’re not just automating workflows, we’re creating infrastructure that can orchestrate itself”, highlighting the importance of building adaptable, autonomous systems alongside reskilled teams.

Strategic reskilling involves:

1. Identifying Future Roles: Analyze which positions are likely to change and map new skill requirements.

2. Developing Learning Paths: Offer structured courses, mentorship, and practical projects that align with business goals.

3. Encouraging Applied Learning: Combine theoretical knowledge with hands-on AI projects for real-world impact.

Example: Amazon introduced Career Choice, a program that pre-pays for courses in high-demand fields, including data science and cloud computing. Employees who participated saw a 15% higher promotion rate and could transition into technical roles in fulfillment centers and operations.

The Economics of Reskilling: A Billion-Dollar Opportunity

Organizations that treat reskilling as an investment rather than a cost see remarkable returns. The World Economic Forum estimates that companies investing in workforce transformation can increase revenue.

Other measurable benefits include:

• Reduced Recruitment Costs: Filling internal roles is up to 50% cheaper than hiring externally.

• Faster Innovation: Skilled employees can adopt AI tools faster, driving efficiency and creative problem-solving.

• Enhanced Customer Experiences: Teams with AI skills can analyze customer data and provide more personalized services.

According to the Future of Jobs Survey, skill gaps are seen as the top obstacle to business transformation, with 63% of employers citing them, leading 85% to prioritize upskilling, 70% to hire employees with new skills, 40% to reduce roles as skills become obsolete, and 50% to transition staff into growing areas between 2025 and 2030.

Emerging AI Reskilling Opportunities for Founders and Investors

Founders and investors can also capitalize on workforce disruption. The AI Reskilling market is projected to reach new financial highs by 2030, making it a fertile ground for startups.

Opportunities include:

• AI Learning Platforms: Develop adaptive tools that personalize reskilling content based on employee performance and career goals.

• Corporate Upskilling Solutions: Offer subscription-based services that help enterprises continuously upskill their workforce.

• Micro-Credentialing and Certification: Enable employees to earn verified credentials for AI and digital skills, making internal talent pipelines more transparent.

Example: Coursera saw a 35% increase in enterprise customers between 2020 and 2023, as organizations sought scalable AI and tech training for their employees. Companies leveraging such platforms can quickly deploy training at scale, ensuring workforce readiness without significant operational overhead.

Implementing a Reskilling Strategy That Works

A successful AI Reskilling program is systematic, measurable, and integrated into the business. Consider the following steps:

• Conduct Skills Gap Analysis: Identify which roles will evolve and which skills are most critical.

• Set Learning Objectives: Define what success looks like for both employees and the organization.

• Leverage Technology: Use AI-driven learning platforms to deliver adaptive, personalized content.

• Monitor and Adjust: Track completion rates, skill acquisition, and business impact to refine programs continuously.

By following these steps, companies can turn workforce disruption into a strategic advantage, creating a resilient and agile talent pool ready for the AI era. 

Reskilling That Delivers Results

AT&T: Scaling AI Skills Across a Large Workforce

• Over $1 billion invested in reskilling programs for AI, cloud, and cybersecurity roles.

• 15% increase in employee engagement over three years.

• Internal mobility allowed 60,000 employees to transition into new technical roles.

Amazon Career Choice: Turning Operations Staff into Tech Professionals

• Pre-paid courses for high-demand technical skills.

• 15% higher promotion rate among participants.

• Enabled fulfillment center employees to transition into AI-enabled operational roles.

Coursera Enterprise Training Programs

• 35% increase in enterprise clients from 2020 to 2023.

• Delivered scalable AI and technology courses for thousands of employees globally.

• Realized measurable improvements in internal skill competency and project delivery times.

All three programs demonstrate how major organizations are investing heavily in reskilling to meet the demands of AI and technology-driven roles. As AI continues to transform industries, these initiatives show that prioritizing workforce upskilling and internal mobility will be essential for companies to remain competitive and harness the full potential of intelligent technologies in the future.

The Future of Work: AI + Human Collaboration

Reskilling is about more than teaching new skills; it is about creating a workforce capable of collaborating seamlessly with AI agents. Employees who understand how to leverage AI become more strategic, more creative, and more efficient.

Opportunities include:

• AI-Augmented Roles: Employees focus on decision-making and creativity while AI handles repetitive analysis.

• Cross-Functional Expertise: Reskilled employees can bridge departments, connecting technical AI insights with business strategies.

• Continuous Learning Mindset: Organizations that embed learning into daily workflows cultivate an adaptive culture ready for future technological shifts.

Example: Salesforce integrated AI-powered tools like Einstein into CRM operations. Sales and marketing teams that received AI training increased productivity by 30%.

Measuring Impact: Metrics That Matter

Effective reskilling programs track both employee and business outcomes. Key metrics include:

• Skill Acquisition Rate: How quickly employees gain the targeted skills.

• Internal Mobility: Percentage of employees moving into new roles enabled by reskilling.

• Productivity Gains: Time saved, increased output, and revenue impact.

• Employee Satisfaction: Engagement and retention rates post-training.

By measuring impact, organizations can demonstrate ROI and continuously refine their learning strategies, ensuring the workforce is future-ready.

Why Untapped Ventures Is Your Partner in AI Reskilling and Workforce Transformation

Untapped Ventures recognizes that AI Reskilling is not just a trend but a critical frontier for founders and investors. We back startups that:

• Build scalable AI Reskilling platforms

• Enable enterprises to implement high-impact upskilling programs

• Deliver measurable workforce transformation

If you are developing solutions that empower employees and enterprises to thrive in the AI era, pitch us. Our early-stage support includes capital, guidance, and strategic connections to help you scale your vision.

Do not hesitate. Pitch Us

FAQs

What is AI Reskilling?

AI Reskilling involves training employees to work effectively alongside AI, develop new tech-related skills, and adapt to evolving roles in the workforce.

Which industries benefit most from AI Reskilling?

Industries with high automation potential, including finance, healthcare, logistics, and customer service, see immediate gains in efficiency and employee retention.

How can companies measure the success of reskilling programs?

Success can be measured by skill acquisition, internal mobility, productivity improvements, and employee satisfaction metrics.

Can startups build profitable businesses around AI Reskilling?

Yes. The AI Reskilling market is projected to exceed $90 billion by 2030, with opportunities in learning platforms, corporate training solutions, and micro-credentialing programs.