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Gather Support for Company Learning on Trailhead

Learning Objectives

After completing this unit, you’ll be able to:

  • Gather support of the business to implement a learning program using Trailhead.
  • List which stakeholders to include in the first meeting.
  • Create an appropriate agenda for the first meeting.
  • Identify team members and set up the team.


So you've decided you want to bring Trailhead into your business. Perhaps you’re looking to drive Salesforce adoption, skill up people managers, start a wellness program, or… you name it. No matter the reason, this module gives you tried-and-tested steps to inspire a culture of continuous learning though Trailhead at your organization.

Regardless of how many people you’re looking to skill up, these steps help you introduce Trailhead smoothly, with no surprises. Successfully introducing a new learning tool requires some organization and planning. Trailhead is a fun and easy way to learn, but it takes more than just sending a Trailhead link and hoping people act on it. Hope is not a strategy, as they say!

Our steps show you how to quickly introduce Trailhead into your business and spur some fun through a launch competition offering prizes and recognition. We call this toolkit Trailhead in a Box because the process is easy to implement and repeat as you scale learning via Trailhead across your business.  

In this unit, we walk you through some first steps.

Get the Business on Board

Before you implement Trailhead as a go-to platform for learning new on-demand skills, you need to gather support and gain approval from your managers and leadership. Keep in mind that you’re asking the business to support and buy into the idea—and to give you time and potentially some resources to run this program. 

Let’s look at what has worked for others at this stage. 

First, set up a meeting to get buy-in with key stakeholders. We recommend that you invite your executive sponsor to the meeting at a minimum, but you might also want to include other key players (more about the team in the next topic). For help on how to pitch the idea, complete the Storytelling & Communication module on Trailhead.

Once you have your list of stakeholders, and the calendar invites have been sent, it’s time to set the meeting agenda. We recommend you address the following important questions in that first meeting.

What is Trailhead? Start with an overview of Trailhead. Use the Trailhead Guide slide deck in the Resources section below to show your stakeholders what Trailhead is all about. 

Why Trailhead? Demonstrate how Trailhead can impact your organization by showing how others have succeeded with it. Find inspiring Trailblazer stories on the Trailblazer website and in the Trailhead Company Stories slide deck (see links in the Resources section below). These Trailblazer stories cover all different kinds of job roles and skills. Use them to create an emotional connection.

What are your vision and desired outcomes for the program? Build a vision of what you aim to achieve through the program and the outcomes for employees and the business. To do this, create an outline that covers:

  • A high-level vision for the program; for example, scaling learning at your company and making it fun.
  • Your target metrics for success for adoption and participation; for example, 100 participants, a 6-week competition, a minimum of 10 badges per participant, and so on.
  • General goals and outcomes; for example, embedding Trailhead as the go-to learning platform, reducing face-to-face onboarding and training by 50%, building a scalable learning solution, enabling X number of employees to achieve Y number of badges, and so on. Note: If you want to increase the challenge for your participants, consider including some credentials such as superbadges or certifications, in your goals.

What are your asks from the business? What are you going to need to make this successful? Outline what you need to run the program, such as:

  • People to support you (we outline roles and responsibilities in the next topic)
  • Space and time to organize and deliver on the goals
  • Budget for swag or prizes

If budget is going to be a showstopper, get creative around how to reward top achievers. Consider prizes like a lunch or dinner with the executive team, PTO, or attendance at a special company event.

Once you get agreement from the business to move forward, you’re ready to build your team.

Identify the Trailhead Team

Now that you have support from the business to drive this program, you need to determine if you can handle this yourself or if you need a little help from your colleagues. As you think through who should help, focus on the goals you outlined earlier to determine who should be involved to make it a success. Depending on the size of your business, this can be one person or many people.

Here are some questions to consider as you define roles and responsibilities. 

Suggested Roles
Who is running the program?
Admin, project manager, change manager
Decision maker for all overarching, long-term plans
Who is sending communications?
Marketing manager, Admin
Authors, designs, and sends communications
Who will support and answer questions?
Defines communication channels, outlines the best way to communicate questions, and directs questions to the appropriate person
Who is owning the content plan?
Identifies objectives, creates the content plan, and creates the trailmix
Who is the executive sponsor?
C-level executive
Supports the competition

Here are some considerations as you move forward with your planning.

  • Identify the executive sponsor. Your sponsor is key to the success of the competition. Find time on their calendar to align with the launch early on.
  • Decide if you need a test group. Some large organizations use a small pilot group to test the content first. Not mandatory, but it’s a useful step if you need a proof point before going big.
  • Determine which users will participate in the competition (your target audience). Is this for a certain business unit or team? You can go as big or small as you want, but to get a healthy competition going, large organizations might want to aim for 100+ people and no less than 50 people, as a guideline.
  • Involve Salesforce. Get your account executive, Trailhead account executive, or customer success manager to come and support your efforts. They might present some content or help bring some swag to the table.

Set Up Your Kick-Off Meeting

To get things started and ensure everyone is aligned, set up a kick-off meeting. Include everyone you identified in the previous step, but make the executive sponsor optional. You want to make sure you get your sponsor’s time later on for your launch, so allow them to opt out of the kick-off meeting. 

Next, create an agenda for the meeting. Here are a few suggestions.

  • Agree upon competition objectives/goals.
  • Agree upon roles and responsibilities.
  • Define the “swag” budget for your prizes.
  • Establish a meeting cadence. We recommend weekly if you want to get your program up and running quickly.


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