It’s easy to imagine the scenario. A customer makes a new software purchase for her business unit. She finds tons of resources to help her get started with the product, but she doesn’t understand where to begin or how long it will take her to get value out of her investment. It’s overwhelming to navigate an onboarding process without a clear learning path to success. As businesses scale and their software products get more complex, they often invest in a wide range of services and tools to help avoid this difficulty.

Acknowledging the Problem 

The customer success technology stack of 2017 is broad, with many tools that are designed to improve the customer experience, and assist the teams that support customers. While models vary across companies, it’s not uncommon to find each resource or tool bubble with a different department or team. These teams often work in parallel, but can have separate management, and depending on the size of the organization, may be completely siloed from one another. As a result, it’s common to see resources scattered between a learning management system, and a knowledge base or help center, with different owners and processes around resource maintenance and expansion.

As training organizations grow, they often become a stand-alone education services department, and aren’t necessarily integrated with the customer success or product support departments. If these departments are in completely different branches of a company, alignment on training and onboarding processes and activities can be difficult to achieve.

Moreover, documentation and help articles don’t provide an opportunity for a cohesive or guided learning experience, and rely on a reactive approach on the part of the business. It can be tiring for customers to search for an answer and have difficulty finding it, especially at the beginning of their customer journey. They may not be aware that they don’t know, which presents a challenge when they face a search bar and lack knowledge on terminology and features of a particular piece of software.

Understanding the Problem

While development is underway in growing software companies, customers are demanding clear paths to success in new ways. As the subscription economy continues to take hold, software purchases are no longer one-time buys. Recurring revenue models rely on renewals, and the lifetime value of a customer is realized over time rather than through a complete up-front purchase.

The threat of competition and lost revenue is real. Customers want to get the value they expect quickly, and they will leave if that value isn’t realized. While customer success managers may serve as the quarterback, making plays and deciding what comes next for their clients, they often depend on the support of their training counterparts to onboard customers and create the path to value. Here are some tips for building a training and onboarding program that’s scalable, while maintaining a cohesive experience for customers.

Make Onboarding Easy

When planning an onboarding process, it’s best to break down the skills that customers need for success by identifying essential knowledge. Customers do not need to know everything about a product on day one. Write down easy wins for achieving value and any critical setup processes that need to occur now for customers to see success later. Simplify these first steps as much as possible without diluting the subject matter.

It’s tempting to plan to walk customers through the software based on the location of features alone. Product tours that hop from feature to feature, however, are hard to reinforce and don’t address users’ goals and use cases as skill-based training does. Documenting this essential knowledge allows for proper organization and prioritization. The topics can be organized across the onboarding phase of the customer lifecycle.

At this phase in the planning process, it’s helpful to partner with customer success or account management. These teams have a strong understanding of common customer goals, and they can serve as subject matter experts in the training development process. Additionally, alignment with these departments can go a long way, as they are usually the teams that are directing customers to appropriate resources on their path to value.

Create Role-based and Goal-based Training

Onboarding can be defined in several different ways. In the section above, I recommend identifying essential knowledge, but it’s also important to recognize that this may be different for various users of a product. If a product has different user types or profiles, it’s helpful to define the purpose of each profile.

One way to get a well-rounded understanding of the different buyer personas that use the product is to work with product marketing, sales or product management. Depending on the company, this expertise will reside in different departments. Persona profiles include detailed information about a typical buyer, such as background, characteristics, goals and challenges. They can also include common use cases and needs, and descriptions of daily responsibilities.

Understanding these personas is helpful for planning role-based and goal-based onboarding content. This type of pathway can often contain a large degree of duplicate content across personas, but provides a more custom and targeted experience. This is also helpful because it provides training professionals with a more concrete understanding of a well-rounded user; knowledge that can help drive a prescriptive approach to onboarding, with real recommendations and best practices. They can then design training experiences that help customers with different needs – integrating the software into their daily workflows and processes.

Cross-link Relevant Resources

A key part of avoiding user fatigue is helping customers easily find the resources they need. Sometimes, this materializes through learning pathways that take learners through a well-defined experience. This can also be accomplished in different ways when more flexibility is needed. Rather than create an onboarding experience that makes users hunt for resources, it’s possible to make additional learning opportunities highly accessible. One way to do this is by cross-linking resources.

This is done by providing access to new content upon completion of a relevant resource. If students are learning through on-demand training in an LMS, direct them to similar help content in the company knowledge base at the end of a lesson. Collaborate with product support or documentation teams to insert links to extended learning opportunities in help content. Actions such as these can encourage customers to learn more about a certain topic or reinforce knowledge through immediate application.

While providing related resources in different formats is a step in a positive direction, it’s also helpful to cross-link prerequisite concepts. If a certain concept requires an understanding of other product features or characteristics, linking to that information enables customers to easily acquire any knowledge they may need to achieve their desired goal.

Set Expectations for Onboarding Early

While the content and format of the learning pathways dictate a large portion of a customer’s onboarding success, another critical component is customer buy-in. Since customer training is often voluntary, customer success and training professionals need to work to ensure that their customers are prepared and committed to the onboarding experience. One way to do this is to set customer expectations around next steps from the sales process through the realization of value. This involves creating a clear process around onboarding and defining the key components within it. For example, one process may contain a project kickoff call and one on-demand training course, followed by two in-person training sessions. Presenting all pertinent details and commitments needed from customers and reviewing this information with the customer early can provide them with more time to plan and prepare accordingly.

After customers understand the stages within onboarding, devise a way to surface progress, so they can easily find information on what they have accomplished so far and what remains to be done. If progress is being tracked in an LMS, it is possible to automate completion triggers and distribute badges. If it’s not, a customer success professional can keep track of the stages on a shared document.

This alone won’t always keep customers on track. Calls to action through mediums such as email campaigns encourage users to reinforce new behaviors and help them get a firm grasp on what needs to happen between each step in the process.


An onboarding program is meant to get a new user up and running on the product. Just as a product manager may conduct user experience tests on a newly developed feature, training professionals can also evaluate the learner experience. One way to do this is to put a cohort of new users into a Beta program. Testing can help evaluate the quality of the training program, highlight any points for improvement, and provide a forum for receiving feedback on the overall experience. Deepen this approach by implementing an A/B test and providing different pathways or processes to different testers. Observe learning, request real-time feedback, and compare success and satisfaction among the groups.