Strategies to Upskill and Reskill Talent This 2026

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Published on
December 3, 2024
Updated on
January 19, 2026
Joseph Burns
Founder

I help companies hire exceptional talent in Latin America. My journey took me from growing up in a small town in Ohio to building teams at Capital One, Meta, and eventually Rappi, for which I moved from Silicon Valley to Colombia and had to recruit a local tech team from scratch. That’s where I realized traditional recruiting was broken, and how much available potential there was in Latin American talent. Almost ten years later, I still work closely with Latin American professionals, both for my company and for clients. They know US business culture, speak great English, work in the same time zones, and bring strong skills and dedication at a better cost. We have helped companies like Rappi, Globant, Capital One, Google, and IBM build their teams with top talent from the region.

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If you’re a company aiming to hire and retain top-quality talent, you’re in the right place. With the business landscape evolving faster than ever, it’s crucial to stay ahead. One of the best ways to do this is by investing in upskilling and reskilling your workforce.

Let’s dive into why this matters and how you can implement it effectively.

What is Upskilling and Reskilling?

       
  • Upskilling is about teaching your employees new skills that enhance their current roles. It's like giving your team new tools to do their jobs better. For instance, a marketing professional might learn advanced data analytics to understand customer behavior more deeply. This keeps employees updated with the latest trends and technologies, which is crucial in a fast-paced business environment.
       
  • Reskilling involves training your employees to take on different roles within your company. This is important when new technologies emerge or market demands shift. For example, a customer service representative might be trained to move into a sales role. They already understand the product and customer needs, so with some training in sales techniques and tools, they can effectively transition to their new role. Reskilling helps your workforce adapt to changes and fill new skill gaps.

Both upskilling and reskilling are essential for keeping your workforce adaptable and competitive in a constantly evolving market.

The Benefits of Upskilling and Reskilling

Increased Employee Retention

When your employees see that you're investing in their growth, they feel valued and are more likely to stick around. According to LinkedIn's Workplace Learning Report, 94% of employees say they would stay longer at a company that invests in their development. Plus, companies that focus on developing their people see a 58% jump in employee retention and a 24% boost in productivity. It's a win-win.

Enhanced Productivity

Skilled employees simply get more things done. When you keep their skills sharp and up-to-date, you're not just helping them—you're boosting your entire operation. Research shows that companies with strong training programs see income per employee that's more than double what companies without such programs see. So, by investing in training, you're setting your team—and your business—up for stronger performance.

Future-Proofing the Workforce

Let's face it, the business world is always evolving. That's why continuous upskilling and reskilling are so important. They prepare your team for whatever comes next, helping to close skill gaps before they become a problem. A World Economic Forum study estimates that by 2025, half of all employees will need reskilling due to changes in technology and job roles. Staying ahead of the curve with training helps your company stay competitive and ready for the future.

Improved Employee Morale and Engagement

When you offer your employees chances to learn and grow, it does more than just improve their skills—it boosts their morale too. People are more motivated and engaged when they see a clear path for advancement. In fact, according to a 360Learning report, 94% of employees would stay at a company longer if they knew it was committed to their development. Engaged employees are not just more productive—they're also more likely to bring fresh ideas to the table and provide top-notch service.

Attracting Top Talent

A strong development program isn't just about keeping the employees you have—it's also about attracting new ones. Top talent wants to work where they can grow and develop. Gallup found that 59% of Millennials say opportunities to learn and grow are extremely important when they're looking for a job. Offering robust training programs makes your company more attractive to the best candidates who are looking for a place where they can build their careers.

Strategies to Upskill and Reskill Your Talent in 2026

1. Customized Training Programs

Tailor your training to what your team really needs. Start by identifying any skill gaps and understanding what your employees want to achieve in their careers. Then, design workshops and courses that directly address these areas. For example, if you're in the tech industry, focus on the latest programming languages or cybersecurity skills. By making your training relevant, you ensure your team stays adaptable and competitive.

2. Offer a "Salad" Upskilling/Reskilling Method

Instead of offering isolated skill options, mix different skills into a well-rounded training program. Think of it like creating a ""salad"" where you blend technical skills with soft skills like leadership and communication. This approach caters to different learning styles and keeps the training process engaging and effective. Your employees end up being more versatile and ready to handle a variety of challenges.

3. Mentoring and Coaching

Pair up your seasoned employees with junior team members. This mentoring relationship creates a supportive environment where knowledge is shared, and skills are developed collaboratively. Regular knowledge-sharing sessions can give your upskilling efforts a significant boost. Mentors bring real-world insights that textbooks just can't match, helping mentees navigate their career paths with more confidence.

4. Continuous Learning Culture

Make learning a regular part of your company's culture. Keep your training materials up to date with industry trends, and provide a platform with various resources for ongoing learning. Encourage your team to seek out new knowledge on their own—whether it's through a company book club, subscribing to industry journals, or accessing online courses. The goal is to make learning a habit, not a chore.

5. Personalized Development Plans

Give your employees ownership of their growth by helping them create personalized development plans. Use self-assessment tools to help them pinpoint their strengths and areas for improvement. Regular reviews keep these plans on track with both personal and company goals. Setting clear, achievable milestones helps employees stay motivated and see their progress as a journey, not just a destination.

6. Leveraging Technology and E-Learning

Take advantage of e-learning platforms and digital tools to offer flexible, on-demand training. This allows your employees to learn at their own pace, fitting professional development into their busy schedules. Platforms like Coursera, LinkedIn Learning, or Udemy offer a wide range of courses that can be customized to meet your team's needs. Plus, using tech tools to track progress and assess skills ensures the learning sticks and is effective.

7. Incorporate Microlearning

Break down training content into bite-sized, manageable segments that can be completed quickly. Microlearning is easier to digest and fits seamlessly into the daily workflow, making it a great way to keep skills sharp without overwhelming your team. Think of it as short videos, quick quizzes, or brief articles that employees can engage with during a coffee break. This approach keeps learning light, frequent, and effective, preventing burnout and ensuring steady progress.

Putting It All Together

Upskilling and reskilling your workforce isn't just something nice to do—it's a must in today's fast-paced business world. By putting these strategies into action, you'll give your team the tools they need to thrive and build a culture of innovation and adaptability.

Ready to take the next step in hiring and retaining the best talent in LatAm? Connect with Lupa, and let's keep you ahead in the talent game.

By Joseph Burns
Founder

Joseph Burns is the Founder and CEO of Lupa, a company that helps clients hire exceptional talent from Latin America. With more than ten years of experience building teams in the US and Latin America, he combines product leadership at global companies with a strong understanding of nearshore hiring and remote work strategies.

Before starting Lupa, Joseph led product and engineering teams at Rappi, one of the biggest tech startups in Latin America. He built local teams from scratch in nine countries. He also worked at Meta and Capital One, where he focused on using data to make decisions and building products for many users.

Since starting Lupa, he has worked with over 300 clients around the world, hired more than 1,000 candidates, and helped reduce recruitment costs by about 60 percent. His clients include top startups and Fortune 500 companies like Rappi, Globant, Capital One, Google, and IBM.

Joseph is originally from Ohio and has lived in Brazil, Colombia, and Mexico. He speaks both English and Spanish and is passionate about connecting talent across borders and creating global opportunities for professionals in Latin America.

Areas of Expertise: Remote hiring and international team building, North America–Latin America recruiting dynamics, talent market insights and workforce strategy, global staffing models and compliance, and cost and efficiency optimization in hiring.

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