How to Become an Always-Learning Company

Shift from random acts of learning to a holistic upskilling program with a clear ROI

Before we begin…

Welcome to the WorkplaceTech Pulse, presented by SHRMLabs. We are expanding our resources to bring you the best possible information from leaders in HR technology and transformation.

My name is Nell Hellem, innovation catalyst at SHRMLabs. You will hear from me as well as my colleagues every other week with the release of each new edition. Let us know any topics you’d like to hear about related to workplace tech and we will consider them for future editions of the WorkplaceTech Pulse.


In today's fast-evolving workplace, the value of upskilling is indisputable. Research consistently demonstrates that companies investing in robust upskilling and professional development programs experience substantial benefits. For instance, Deloitte reports that organizations with a strong learning culture are markedly more innovative, productive, and profitable. Guild Education's data shows a remarkable return on investment in career education and upskilling initiatives. Beyond financial gains, upskilling fulfills critical employee needs, from job security to self-actualization, contributing to overall job satisfaction and retention. Despite these clear advantages, many companies still engage in disjointed and inefficient learning activities. By adopting a strategic, integrated approach to upskilling, companies can unlock significant returns and foster a more skilled, motivated workforce.

I’m excited to introduce this edition’s contributor, Steve Gilman, CEO and co-founder of OneRange. Steve, over to you!

Steve Gilman

Thanks, Nell! I’m Steve Gilman, CEO and co-founder of OneRange, an AI-driven upskilling marketplace. Early in my career, I had the fortune of receiving exceptional training and development—first through my experience playing professional baseball for the Detroit Tigers and later as an Intelligence Officer working for the U.S. Department of Defense (DOD) with Naval Special Warfare.

After earning my MBA from Columbia Business School and joining the private sector, I was surprised to find that the vast majority of corporate skills development programs—even at highly successful companies—did not provide anywhere near the level of support I received as part of my elite training programs. I have since made it my mission to bring best-in-class methodologies from sports and the military into the corporate world for the betterment of businesses and employees alike.

I’m excited to talk to the SHRMLabs audience about how they can implement a holistic upskilling program that will transform their organization into an always-learning company.

Be sure to check out all of our editions of the WorkplaceTech Pulse!

The Data on Upskilling is Clear: It Works

Numerous studies have shown that when companies invest in quality upskilling and professional development, it pays off. To cite just a few examples: Deloitte found that companies with a strong learning culture were 92% more innovative, 52% more productive, and 17% more profitable than their industry peers. Similarly, career development provider Guild Education found that their partners generated an average of $2.84 in savings from every $1 invested in career education and upskilling—an impressive 184% (return on investment (ROI).

When you combine the benefits of boosting innovation, productivity, and employee retention with the reduction of operational errors, employee turnover, and new-hire ramp-up time, the net gain is clear—and probably grossly underestimated by most executives. I encourage you to check out Learn to Win COO Sasha Seymore’s terrific article in this Workplace Tech Pulse series, which includes a calculator for thinking about some of these costs and benefits.

Today’s Employees Are Demanding Better Upskilling

Quality upskilling doesn’t just translate into dollars and cents on company earning statements. It also provides meaningful benefits to employees over the course of their careers. I’m still benefiting from the training I received from professional baseball and the DOD, and I’m sure many of you can cite similar experiences.

To better understand—and visualize—some of the benefits offered through upskilling, I often use the analogy of Maslow’s Hierarchy of Needs (image below). The items at the bottom of the pyramid are foundational for human survival. They are basic needs that must be met in order for people to pursue higher-order wants and needs. The concepts at the top of the pyramid are the things that lead to true happiness and fulfillment.

Image from

Upskilling addresses all levels of the pyramid. Basic corporate training, including operational training, compliance training, and competency training, provides workers with safety, security, stability, and the tools and resources they need to maintain gainful employment and do their jobs effectively.

Professional development fits into the top two categories of self-esteem and self-actualization. Developing broad new skills and competencies enables feelings of independence and self-worth. It also provides the opportunity for external recognition and status as well as the internal belief that one has reached one's true potential, both of which can be extremely powerful and motivating.

Employees today are demanding that their upskilling wants and needs be met and calling on organizations to level up—and walking out the door if they don’t. In a survey by Iconiq, 78% of exiting employees cited a lack of professional development and growth opportunities as their main reason for leaving their company. Why are so many organizations getting upskilling so wrong?

Most Companies are Still Doing Random Acts of Learning

Organizations are spending $367 billion annually on learning and development, so it’s not that they’re not making investments. It’s just that it’s fragmented: A college tuition reimbursement program here. A LinkedIn Learning subscription there. The occasional workshop or offsite retreat. In fact, upskilling is happening in so many different venues and formats that many companies don’t have a clear picture of everything they’re doing, much less a strategy.

For the marketers among us, it’s the difference between doing a bunch of random marketing “activities” and having integrated campaigns that support a clear strategy. Or, for those sports fans, it’s like a series of plays you know how to execute versus a comprehensive gameplan for how you will win.

Most companies lack centralized management of upskilling activities and have little to no meaningful data on program impact. As a result, HR leaders often have trouble making the case for future upskilling investments and programs suffer from a lack of executive buy-in.

The experience for employees is even worse. Many employees forget that they have upskilling programs or have trouble accessing them. Average participation hovers around a dismal 10%. And, if employees don’t participate in upskilling, then neither they nor their companies can experience the benefits of those investments.

Some of the most common reasons for low participation in fragmented upskilling programs are:

  • Administrative burdens. It’s too difficult to get approval for upskilling programs or takes too long to process payments and get reimbursed. These barriers often disproportionately impact employees with less power and less financial means.
  • Mismatch of content. Content that is insufficiently curated, not individually targeted, or otherwise low quality or inconvenient.
  • Unclear payoff. Learning is not effectively rewarded or tied to performance goals, promotions, or pay increases. Some training may even be irrelevant—only 12% of employees reported applying skills learned through typical training to their jobs, according to 24x7 Learning Inc.
  • Lack of time. Upskilling is not well integrated into daily activities and feels like a separate, additional burden on top of existing, demanding workloads.

These barriers might seem nearly impossible to overcome, but I’m here to tell you they’re not. With some key strategic shifts and targeted investments, companies can transform their programs from random acts of learning into truly holistic upskilling with a clear ROI.

Start with the Basics

The first step I recommend you take is figuring out where you stand by conducting a self-assessment of your upskilling program to determine a baseline. This should include the following activities:

Document all your programs. Compile a list of all the various upskilling programs at your company. This may include:

  • Onboarding for new hires.
  • Training is delivered through a learning management system or other means, including operational training, compliance training, and competency training.
  • Undergraduate and graduate tuition reimbursement programs.
  • Coaching and mentoring programs.
  • Onsite workshops and offsite retreats.
  • Technical certifications.
  • Executive education.
  • Learning stipend programs.
  • Course hub subscriptions.
  • Conference stipends (for learning-focused, nonsales events).

Conduct a survey. Create a survey to solicit feedback from employees and executives about how your upskilling programs are working for them. Your survey might include the following information—you can use our handy OneRange Employee Survey template  to get started.

  • Overall, how satisfied are employees with your upskilling opportunities?
  • Which upskilling programs are your employees participating in, and how often?
  • If they are not participating in upskilling programs, what barriers are preventing them from doing so?
  • How relevant do your employees feel your upskilling programs are to their jobs, and how often do they apply skills gained to their jobs?
  • Do your employees feel like the level of upskilling you offer is sufficient, or do they want more?
  • How highly do your employees prioritize upskilling? How highly do they think their managers and executives at the company prioritize upskilling?
  • What additional upskilling programs would they like to see?

Capture data about program success. Gather as much data as you can about the success of your upskilling programs. This may include the following:

  • What is your upskilling budget (across all the programs you documented in step 1)? You should invest at least 1% to 6% of the dollar amount of employee salaries into upskilling—we recommend 3% to 6%.
  • What is your overall upskilling participation rate?
  • What types of programs are your employees participating in the most, and what specific skills are they seeking to gain?
  • Try to come up with an ROI estimate for your upskilling investments. Again, use Sasha Seymore’s calculator or check out this article on the OneRange blog  about calculating ROI.

Explore Deeper Integrations

Once you’ve got a high-level picture of the upskilling landscape at your company, the next step is to figure out how to take your upskilling to another level. That means infusing a culture and practice of learning throughout your company and reducing any barriers to participation that may exist. Consider taking the following actions to do this.

Make learning easy to find

It sounds obvious, but make sure it’s easy for employees to find all the information they need about your upskilling programs. Try to create one central location for this information, such as an intranet or dedicated upskilling platform, rather than burying it in a web of policy documents.

Eliminate reimbursement headaches

Simplify approval and payment for upskilling programs. If following a stipend program, use company-approved credit cards rather than requiring employees to use their personal credit cards and get reimbursed. Better yet, consider an upskilling platform that includes automatic payment processing so that employees don’t have to take an extra step. We consider this so important that we’ve simplified and automated as much of the approval and payment processes as possible through the OneRange platform.

Make time for learning

Think about ways you can carve out time for upskilling. This could include activities such as:

  • An annual Learn-a-Thon or Day of Learning (similar to an annual volunteer day).
  • Hack-a-thons.
  • Integrating time for learning within sprint cycles (e.g., Friday afternoons the second week of every sprint).
  • Meeting-free Wednesdays.
  • An off-site retreat.
  • Quarterly learning goals.

Incorporate learning into core values

Take a look at your company’s core values, and assess whether learning is captured in your language. If you want to truly embrace a learning ethos and become an always-learning company, your core values should reflect your commitment to upskilling. Executives must also buy into this commitment and make efforts to mention it when they talk about your core values to internal and external audiences.

Map upskilling across the employee life cycle

Consider key moments in the employee life cycle, and think about where you can enhance upskilling programs to support individuals through these transitions. This includes:

  • New hire onboarding.
  • Transitions to management roles.
  • Lateral promotions to a new team or department.
  • Transitions to executive roles.

Here are a couple more advanced-level steps you can take:

  • Analyze role rubrics. Many companies have detailed rubrics and job descriptions about the skills required to succeed at each level. Assess the skills outlined in those rubrics, and design upskilling programs to build those specific skill sets.
  • Create learning pathways. Create integrated upskilling programs or a series of courses and activities with the explicit goal of helping employees develop a defined set of skills required to advance to the next level or receive a promotion.

Offer choices in upskilling

We believe that employees know best what they want to learn. That’s why it’s so important to offer a wide variety of choices in upskilling resources. Provide options across the following variables:

  • Content format: courses, books, conferences, coaching.
  • Learning styles and modalities: online or in person, group or one on one.
  • Schedule and timeline: short format or long format, synchronous or asynchronous/on demand.
  • Skills and themes: technical skills, soft skills, personal interests, and wellness.
  • Cultural context: available across time zones, learning offered through affinity groups.

We think an open marketplace is the best way to do this, which is what we’ve created at OneRange. We aggregate top-rated learning resources across incredible upskilling providers such as Coursera, Udemy, Skillshare, and Masterclass while also allowing individual employees to add any resources they may find elsewhere once it’s approved.

Make learning targeted and individualized

Choice is critical, but it’s only helpful if people can actually find what they want. One way to help employees find the best resources is by leveraging the power of your team, including managers and peers. You can use Slack channels or other centralized communication channels to do this. We’ve also built peer and manager recommendation tools into the OneRange platform so employees can easily see what their colleagues and teammates are doing and managers can directly assign upskilling resources to individual employees or groups.

Technology has a big role to play here. In the OneRange platform, we’ve captured a wealth of metadata about all our upskilling resources and then tagged and categorized it according to  key skills and competencies. Using AI-powered recommendations and discovery tools, we can surface the most relevant upskilling resources to individual employees based on their interests and stated goals. Individualized dashboards then enable them to see exactly what they’ve learned.

Measure What Matters

If you’ve taken any of the steps outlined above, then you’re already well on your way to transforming your upskilling activities into a holistic program! The final step is to make sure you’re capturing data to report on the success of your program and ideally some measure of ROI. You’ll need this information to continually improve your program over time and make the case to executives for additional investments.

Develop a plan for how you will track the following information:

  • Upskilling participation and completion rates.
  • Most popular upskilling resources and topics.
  • Total spending on upskilling.

Ideally, you should capture the information in a format that allows you to analyze it to answer key questions such as:

  • Which teams are doing the most upskilling?
  • Which managers are most involved in upskilling?
  • How does upskilling participation vary by role and demographic?
  • How is learning contributing to employee performance and promotion?

Tie learning to performance

Tying learning to performance can be one of the trickiest, but most important, parts of the ROI equation. One of the key ways we’ve found to do this is by incorporating upskilling into annual performance reviews. Employees should have at least one or more specific goals or objectives and key results related to upskilling with measurable outcomes.

Annual reviews should also include an assessment of employees’ skills and—critically—recommendations for specific upskilling resources to help them improve in targeted skill areas. We recently signed a deal with the SHRMLabs peer Confirm and are pursuing partnerships with other performance platforms to make this a more seamless process. We believe this approach will be key to boosting employee motivation and participation in upskilling programs, as well as allowing companies to capture critical data about how participation in upskilling relates to employee performance.

Pay for performance

Finally, once you start capturing real data about your upskilling programs, you may find that you’re paying for a lot of programs your employees aren’t actually using. This is often the case with many course hub subscriptions, for example. Companies frequently pay for enterprise subscriptions based on their number of employees, but only a fraction of employees actually use them.

Prioritize programs that have a business model where they only earn when your employees learn. That way, you can be sure that they’re fully invested in your success. One of the more revolutionary changes we made to the OneRange platform was making access for companies free once they pay a small implementation fee. This approach has been game-changing for enabling companies to ramp up investments in upskilling while having the peace of mind that every dollar spent goes directly toward meaningful learning.


Many companies have great intentions around upskilling. But fragmented programs, low employee participation, and limited data mean that neither they nor their employees are reaping the full benefits of these programs. By removing barriers to participation, increasing choice, improving individualized targeting, and mapping programs across the entire employee life cycle, you can move along a path toward a more holistic upskilling program with clear ROI.

There are many ways to do this, and one of them is by using a tailor-made technology solution like OneRange. Our open content marketplace, automated payment and approval system, AI-powered tagging and recommendations, and pay-per-use model ensure that upskilling is centrally managed and tracked to the dollar. We invite you to check out our platform at and let us know what you think—we’re improving it every day based on feedback from clients and peers like you. And you can read more thought leadership like this article on the OneRange blog.

OneRange is an intelligent upskilling platform that connects companies and employees to world-class learning resources through a revolutionary open marketplace, pay-per-use pricing, and unrivaled intelligence powered by Al.  Join the upskilling revolution at

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