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Overcoming Challenges to Build a Scalable Onboarding Program

| 8 min read


Onboarding is arguably the most important program that sales enablement is charged with implementing. It is the first impression new employees get of the company they’ve decided to invest their talents in and lays the foundation for each employee’s potential for success in their role. A positive onboarding experience can accelerate a new sales rep’s productivity while a subpar onboarding experience can slow down ramp time. Onboarding is essential to execute well, but it is tough to do effectively at scale.

As organizations grow, whether it’s a startup or a Fortune 500 company, they face a number of challenges to scaling their onboarding program to get new reps productive as quickly as possible. Here are five common areas companies often stumble over when building a scalable onboarding program and tips to overcome them.

Boiling the Ocean

Especially as a company is growing or as a function is growing, more teams that are being built out begin demanding role-specific training. This causes sales enablement professionals to feel like they have to cater to the entire company, to all the different roles. While that’s obviously a dream for many sales enablement practitioners, there simply are not enough hours in the day, and often not enough hands on deck on an enablement team to tackle role-specific training for every person across the company.

Instead of attempting to “boil the ocean”, focus on the 80/20 rule. Prioritize the 80% that applies to everyone and if it isn’t clear what that common factor is, consider the customer. The customer is one thing all roles have in common, regardless of department – whether you are customer success or engineering – so train people on how to support the customer. Center onboarding on helping everyone understand the use cases, the personas, the challenges, and how the company supports the customer better than the competition.

Be strategic in thinking through where to put resources. This is not to say that craft programs should be ignored, but often a lot of that work can be crowdsourced. Partner with the leaders and superstars in those specialized teams to help build out what an onboarding plan would look like, and then streamline it so that it doesn’t necessarily rely on sales enablement to govern. Boiling the ocean is an easy trap for sales enablement to fall into, but there are ways around it.

Misalignment Across Departments

When changes and growth move fast, the harder it is for sales enablement to stay connected with all these moving parts, from marketing to product and the field. By letting that gap grow, practitioners do themselves a disservice not only for onboarding, but for all enablement initiatives.

It is in the best interest for sales enablement to be at the table with the product team when they are deciding when the next release is going to be, with the marketing team when they are working on messaging, and with the sales team when trying to understand if the customer is actually benefiting from enablement initiatives. In making sure that those teams are aligned, be maniacal, disciplined, and really passionate about building relationships with the leaders and having frequent touch points with those teams.

Cross-functional collaboration is critical to onboarding, so establish a feedback loop from marketing, product, and the field.

First-Line Manager Enablement

At the end of the day, first-line managers are the amplifiers to the field. They are the ones that are going to be able to help sales enablement roll out each new process and avoid preventable mistakes. Meanwhile, they are also the ones that are going to help ensure that the feedback that has been going to the field is something that is productive.

There is nothing worse than doing an onboarding program and having someone say that their manager told them not to do something the way that is being taught to them in the session. This creates unnecessary confusion that could be avoided by prioritizing the enablement of first-line managers.

It is common for sales enablement practitioners to assume that managers know what good looks like, that they put on the manager hat so now they must be able to know how to coach and how to facilitate. The truth is that often, they do not naturally know how to manage people. Many first-line managers are star performers that were promoted, and they do not yet have management or leadership experience. Sales enablement practitioners need to take the action of providing them with the resources and toolkits they need to manage so they are equipped to help enablement avoid skill-fade with the team long after onboarding has happened.

High Touch Engagements

As companies grow into different regions and expand teams with different roles, a one-size-fits-all approach to enablement, and especially onboarding, will no longer be sufficient. However, it can be difficult to provide personalized engagements with a high volume of people and large variances in role responsibilities. This is where cross-departmental collaboration and manager enablement collide and really become invaluable.

Lean heavily on managers across the various departments to be the amplifying factors to extend enablement to their teams. Create toolkits and be very intentional in coaching to help managers be tactical in how they are building up their teams during the onboarding phase.

Another important piece for scalable high touch engagement is the tech stack. Consider how technology can help simulate high touch engagements to help expand the reach that sales enablement is capable of and make the concept more scalable.

Behavior Assessments

When it comes to assessments, practitioners can do LMS tests or facilitate quizzes and get a number to indicate how well a rep will perform in a particular area. The challenge with those numbers is that they hide a wealth of information. It is just one data point, and while it is a valid data point, it is just one out of many that are needed to triangulate what is happening.

In terms of certifications, behavior assessments can be a much more valuable area for sales enablement to spend their time. In behavior assessments, reps actually have to complete a task in front of a panel and are judged on certain behavioral attributes on a scorecard to determine that they have achieved the minimum requirements for certification. Then, they are able to get very prescriptive guidance on the things that they are missing and where to go next to build that skill.

To scale those behavior assessments when the sales force is growing, technology can be critical. Prioritize tools in the tech stack that can support that. For example, use a platform where a video can be uploaded and reviewed remotely so that feedback can be provided just-in-time to reps. While this format will be more manageable at a higher volume, it will also help mitigate other obstacles such as onboarding across time zones.

Sales enablement practitioners should invest their time and energy in creating learning experiences that lead to behavioral outcomes that can be observed, monitored, and coached individually, even after reps leave the onboarding program.

As companies scale, it’s important for the onboarding program to be strategic in how it adapts to the changing needs in demand and format. While there are a number of challenges that sales enablement needs to be mindful of to avoid problems down the road, practitioners can overcome these obstacles to effectively scale onboarding with thoughtful planning.