Smartsheet Moves to an eLearning Platform to Help Drive $1M Revenue Target

Skilljar succeeded where previous LMS failed to deliver on monetization strategy

Smartsheet Moves to an eLearning Platform to Help Drive $1M Revenue Target

Skilljar succeeded where previous LMS failed to deliver on monetization strategy

The Challenge

Smartsheet wanted to launch online training with an eCommerce component to drive revenue. The goals were to create a scalable, impactful customer education program and shift from providing a free experience to a paid/premium option. Their previous LMS of more than five years was not equipped to handle the monetization component.

The Solution

Smartsheet partnered with Skilljar to create Smartsheet University so that users could learn how they wanted—from self-paced eLearning to virtual instructor-led training (VILT) to in-person regional events. Through a Skilljar/Stripe integration enabling their eCommerce platform, Smartsheet users can gain access to pro-level support through licensing plans, while non-licensed visitors are able to purchase content a la carte. They also created paid certification exams in Caveon delivered through Skilljar, along with badges and certificate credentials.

The Results

Since launching with Skilljar in 2017, Smartsheet University has seen steady year-over-year growth. As a result of switching to Skilljar, Smartsheet has diversified their offerings to include a paid eLearning component in support of a $1M+ annual revenue target, which they are well on track to reach.


Smartsheet was using its previous LMS for more than five years to offer limited training options to customers. They wanted to launch online training with an eCommerce component to drive revenue, however, their previous platform wasn’t equipped for this.

Smartsheet wanted to create a scalable, impactful Customer Education program and shift from providing a free experience to a paid or premium option.

The goals for monetizing their education program aligned with their two training catalogs:

ILT & Certification Catalog

  • Monetize programs as a revenue stream
  • Increase product adoption and usage
  • Upskill users on product capabilities and application
  • Serve up a credentialing program so students can take exams, track progress, and earn certification

Self-paced Catalog

  • Deflect support cases to self-service options as a way to save money on support resources
  • Ensure users are prepared to use the Smartsheet product to encourage licensing and account renewals
  • Encourage account expansion, pro-level support, and license upgrades
Holistically, Skilljar offers more for us than any other LMS vendor has to date.
Stephanie Barbee
Senior Manager, Customer Training, Smartsheet
We hope that every human can find value in Smartsheet University.
Damani Musgrave
Skilljar is always improving and integrates with an ever-increasing sphere of applications.
Damani Musgrave
We got a database dump from Docebo and imported everything into Skilljar. Skilljar implementation managers were very helpful with this transition.
Damani Musgrave
Skilljar enabled us to roll out a virtual eLearning program in a way that aligned to the existing offerings we already had on the platform.
Stephanie Barbee
This approach enabled our sales organization to start adding training to more opportunities with significantly less friction. We sold just shy of about a million dollars in subscriptions in the first six months of that program launching.
Stephanie Barbee
Skilljar really helped us relaunch back into in-person training so we can offer more ways for our customers to learn.
Stephanie Barbee
Free training does not guarantee consumption by your target audience.
Stephanie Barbee
Skilljar collects a lot of consumption data which we look forward to incorporating with our customer account data.
Damani Musgrave
Skilljar has been a pivotal vendor because they provide a direct-to-customer purchasing experience, a function not widely available with other vendors. This has elevated our program internally within the ranks of Smartsheet because we can drive revenue through the tool.
Stephanie Barbee
As a result of switching to Skilljar, we have the ability to structure learning experiences that get us closer to our ideal state of customer education at Smartsheet.
Damani Musgrave
We’re continuing to see higher volumes in our subscription plans sales, and our a la carte offerings remain a great way to test out new content and different learning experiences to our customers.
Stephanie Barbee


Smartsheet partnered with Skilljar so that users could learn how they wanted — from self-paced eLearning to virtual instructor-led training (VILT) or regional in-person instructor-led education (ILT). In the early years, they used Skilljar for their self-paced eLearning option, offered as either free or bundled into another product or service.They launched Smartsheet University in 2017 to provide a path to individual enablement with their products, i.e., learners can own their career path by advancing their skills with Smartsheet University. The transition from their previous LMS was straightforward.

In July 2020, Smartsheet went live with newly revamped training options for customers. Their self-paced, eLearning catalog stayed the same, but the paid custom training was delivered fully remotely through Zoom and was largely targeted at onboarding new users of the software in groups of 25 or less. The simple, unified agenda provided a way to quickly bring in more trainers to help support the program as it shifted to virtual delivery.

In the summer of 2021, Smartsheet launched a subscription plan for their VILT catalog and rebranded their complete program with “learn the way you want options” as Smartsheet University (SmartU).Their monetization strategy works on three levels:1. A subscription model – Companies purchase licenses for a certain number of users to access Smartsheet University courses. (Through their eCommerce platform, made possible by the Skilljar integration with Stripe, Smartsheet users can gain access to pro-level support through licensing plans.)2. A self-service model – Users can quickly get the information they need, saving valuable support resources. (Non-licensed visitors are able to purchase content a la carte.)3. A certification program – Users pay to complete courses that will earn them a badge or certification in Smartsheet products.

Smartsheet creates certification exams in Caveon, which they deliver through Skilljar, along with badges and certificate credentials. Learners can earn certifications in Core Product, Project Management, and System Administration. Learners can also earn completion badges in Core Product, Project Management, and Control Center Blueprint Builder by passing the related courses and quizzes. These certifications demonstrate applied knowledge and skill within the Smartsheet platform.In June 2022, Smartsheet was delighted to relaunch their one-to-many in-person learning offering, branded “SmartU Live Regionals.” They’re actively working to build out that catalog and expand live events to more cities.

Who uses Smartsheet University?

Smartsheet University users run the gamut from those who are new to the product to those who are certified experts in the software.A new user might be someone tasked with managing a complex workstream that was traditionally cobbled together with email and Excel. This user might have been given a license from their company to use Smartsheet to execute a workflow plan. This user needs to access training to know what to do after they log in to Smartsheet for the first time.Similarly, people come to Smartsheet on their own after hearing about it from a friend or colleague or visiting the website. This could be a project administrator who introduced Smartsheet to their company and now they are the system admin and need to understand how to get the most from it.

Some users are looking to self-serve. These users want to learn on their own without waiting for support responses whether they are in charge of the system at their company or a user of it in their everyday work.Lastly, users who are looking to advance their existing skills through certification also come to Smartsheet. They may be advocating for themselves at their company or in the job market. Knowledge of Smartsheet then becomes a key skill they can offer their leadership or that can open networking opportunities for them. Once they have established themselves as an expert in Smartsheet, they may want to take refresher courses to keep up their credentials and stay relevant in the workforce.

Considering Monetizing Your Training or Certification Program?

Designing instructor-led, on-demand paid sessions was uncharted territory for Smartsheet.  Stephanie Barbee is their Sr. Manager for Customer Education. Her team leverages the Skilljar LMS to enable eCommerce through Stripe and offer certifications and badges through Caveon.

Here is how Smartsheet launched a monetization strategy, along with Stephanie’s tips for success.

Smartsheet launched a virtual instructor-led training (VILT) catalog in July 2020. Prior to the catalog going live, customers primarily consumed training through their free “Help & Learning Center” or complimentary access to the self-paced eLearning catalog.

Learners select individual courses or curated learning paths from the available topics, pay for them by credit card, and then choose the date/time that suits their schedule to take the course. Initially, Smartsheet focused on the core capabilities that a new user might need to get started with the product, then added more role-based or use-case specific learning paths. To ensure learners get the most value out of their purchase, they provide 30-day access to the session recording.

Here are Stephanie’s tips for monetization success:

  • It’s reasonable to start with 100% free learning, but don’t hesitate to test paid options early in a program’s evolution. Iteration will allow content to improve and pricing to adjust with demand.
  • Start small when scheduling VILT sessions to create a sense of paucity to drive behavior.  You can always add more in the future.
  • Offer blended learning options. The best experiences are influenced and driven by the learner, which means giving them choices and providing content that supports those choices.
  • Don’t lowball the price. Setting the session or path price higher enables you to “discount” or run promotions to test the customer price tolerance.
  • Customers attribute value according to a “purchase” or “published” price. If they have to pay something for the experience, it will be more highly valued than one that is offered at no cost.
  • Success metrics should be part of the planning process when making the shift to paid services. Examples include:
    • Total volume of sales/bookings for the program
    • Recognized revenue (if that is relevant)
    • Impact to product or subscription bookings/sales
    • Growth of product usage or adoption (or both)
  • Know where usage data at your company is stored and how it was measured by other teams within your organization. This will help align LMS program performance with already established metrics.
  • Set success measures with the C-suite that are not wholly related to revenue/sales. This will help enable the program to show impact and maintain support during the initial rollout of paid/premium offerings. Ask your C-Suite what metrics they find meaningful and enable easy access to that data. More business impact = more leadership support.
  • Whenever possible, beta test or pilot your learning experiences.

Why Skilljar is Better Than a Homegrown LMS

The customer education team at Smartsheet consists of  Stephanie Barbee, Sr. Manager, Customer Training; Damani Musgrave, Sr. Learning Experience Designer; Tim Leavitt, Credentials Manager; and Melissa Metzger, Manager eLearning Experience. Here is their advice, based on experiences using homegrown LMSs and other tools available on the market.


My previous role consisted of 100% instructor-led training without a platform for self-paced consumption. The team would record sessions and share them with clients. I  built a training team that worked to improve the customer learning experience through a major application change. The scalability of an LMS is a tool I would have wanted in my previous work life.
The lack of an online learning environment meant training wasn’t as scalable as it needed to be. This would have simplified how customers consumed the learning content.


Several years ago, I led a small team that built a homegrown LMS. My biggest takeaway is that
the money you spend developing, integrating, and maintaining a custom build can often be comparable to or greater than the cost of a market-tested solution. And then the folks who created that custom build leave the company and nobody understands it well enough to keep it running.


At a previous company, we used an in-house LMS that was tailored to our business needs. While it was intuitive for our customers to use, we had shared technical resources so any changes or adjustments to the system needed to be planned out well in advance. My advice would be to
look for eCommerce functionality when selecting a product and consider the web tools they offer. How easy is it to administer? How much control do you have? Look at the training offered by the vendor and consume it for yourself before making a decision.


Most of my background is in Higher Ed using tools like ANGEL Learning, Blackboard, Moodle, Canvass, and Smart Author, which is revenue-focused.
My background in higher education motivates me to get more people into training and get them learning.


Since launching at the end of 2017, Smartsheet University has seen impressive growth in the percentage of active students and enrollments versus the previous year.As a result of switching to Skilljar, Smartsheet has diversified their offerings and brought more revenue to the business with an easy eCommerce solution. From a financial perspective, the program has become self-sustaining, and their CFO is more than pleased with the revenue it has generated for the company.

Smartsheet University’s offerings include weekly VILT events, in-person training in multiple US cities, custom training packages, and three professional certifications—all in support of a $1M+ annual revenue target.

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