Salesforce Trailhead: How two teams converged to blaze a new trail

The San Francisco chapter’s January 2016 meeting featured Lauren Grau and Kim Shain, both from Salesforce, Inc., presenting Salesforce Trailhead: How two teams converged to blaze a new trail.

Something New Under the Sun

Most technical communicators would agree that when it comes to information products, Ecclesiastes 1:9 has it right: What has been will be again, what has been done will be done again; there is nothing new under the sun.

On the other hand (and with apologies to George and Ira Gershwin), there’s Gershwin’s theorem: It ain’t necessarily so. Salesforce Trailhead reinvents the way new Salesforce developers, administrators, and users learn Salesforce. Rather than an online help system or traditionally structured tutorial, Salesforce Trailhead uses gamification to lead learners along a series of virtual hiking trails. Each trail in turn comprises a set of targeted learning challenges.

Underlying Trailhead’s innovative approach is the integration of marketing automation and social media into Trailhead’s game-oriented learning cycle. To both encourage learners to begin and then keep going, and to provide learners with a visible measure of their progress, Trailhead:

  • Awards publicly displayable points and badges when learning challenges have been completed
  • Highlights learners’ successes on community profiles
  • Celebrates the completion of learning challenges on social networks

Providing clear feedback to individual learners in the form of points and badges, while at the same time enabling one to measure one’s progress against other learners, has made Trailhead unimaginably popular with its large and growing community of enthusiastic Salesforce developers, administrators, and users.

Salesforce Trailhead truly is something new under the sun.

Two Teams, Many Contributors, One Goal

The subtitle of Lauren and Kim’s presentation — How two teams converged to blaze a new trail — merely hints at the complex set of collaborative interactions required to design and deliver Salesforce Trailhead.

In many companies, tech pubs, marketing, and product development refer to each other as “those guys”. Or worse. But when it came to Trailhead, Kim and Lauren needed to make collaboration between the documentation, marketing, and Trailhead product development teams more than a management buzzword.

And they needed to do it quickly: To enable Trailhead to be soft-launched at Dreamforce 2014, the project team needed to deliver an initial version of Trailhead, including an initial set of learning challenges, in only ten-weeks.

The combined team first needed to understand each other’s different working styles and technical vocabularies. Shared values and mutual trust enabled the unified project team to create Trailhead learning challenges at the same time that the product was being developed.

At the time that Kim and Lauren delivered their presentation to the chapter, they were able to provide the following concise retrospective on their teams’ successful collaboration:

  • Focus on shared goals and principles: Use shared values to make decisions and resolve differences of opinion, be sure your assumptions about terminology, et cetera, are valid.
  • Commit to a deadline: A tight delivery date can be made to work to your advantage, focus on delivering a minimum viable product.
  • Assemble a critical mass of supportive stakeholders: Start with a proof of concept (or two), be sure to market the project internally.
  • Put customer needs first: Love your community, don’t be afraid to try something new.

But Does It Work?

Trailhead was an immediate success. Two weeks after going live in October 2014, Trailhead generated more than 1,500 social media postings and more than 20 community-authored posts. By the time Kim and Lauren delivered their presentation to the S.F. chapter on 20 January, 2016, Trailhead’s adoption rate comprised:

  • Month-over-month growth in active users of 40-percent
  • Month-over-month growth in badges earned of 50-percent (more than 250,000 challenge-completion badges so far)
  • More than 175 user-authored blog posts praising Trailhead
  • More than 71 modules and projects

Obviously, then, Trailhead is working. So well, in fact, that one year after its soft-launch, Trailhead was a featured presentation at Dreamforce 2015.

Maintaining User Momentum

Behind Trailhead’s impressive-user-acceptance numbers was another key contributor to Trailhead’s success: sophisticated data collection and analysis.

Trailhead’s criteria for success was defined as the:

  • Number of learning path page views
  • Number of Trailhead learners who completed at least one challenge
  • Number of learning challenges completed across the entire Trailhead users community
  • Percentage of new Salesforce developers who became active

To achieve those goals and keep Trailhead learners on the figurative trail, Lauren’s Trailhead Marketing group constructed an action-based, personalized marketing campaign that, among other things:

  • Tracks and incentivizes learner activity, not just page views
  • Guides different categories of Trailhead learners to the appropriate trails and challenges
  • Uses targeted email to encourage learners to remain active
  • Announces new content to Trailhead users
  • Conducts Trailhead Live global meet-ups, webinars, and workshops

The key point is that another of Trailhead’s important innovations is the recognition that it’s not numbers alone that matter, but rather how those numbers can be used to measure, and if necessary improve upon, Trailhead’s ability to transform new Salesforce developers, administrators, and users into committed Salesforce customers.

References And Links

When discussing the many challenges required to build Trailhead’s collaborative Developer Marketing + Doc & User Assistance team, the presentation cited the following two books:

  • The Collaboration Imperative by Ron Ricci and Carl Wiese
  • Behind the Cloud by Marc Benioff

You can also experience Salesforce Trailhead for yourself at

About This Review’s Author

Riley VanDyke has been a contract and consulting technical writer since 1998 and is an STC-SF chapter volunteer.

President’s News and Notes

As we start this new year off right, I want to first say a special thanks to all our Chapter volunteers: Mysti, Marie, Monica, Marc, Riley, Hallie, and Bonnie. You all make the Chapter possible!
Interested in being part of the club? We have a bunch of volunteer opportunities available, most of which can be completed with your laptop from the comfort of your couch.
Twitter Manager – Update our Twitter feed.
Volunteer Coordinator – Emails and updates volunteers on tasks.
Hospitality Coordinator – Backup for the meeting greeters (must attend the meeting in this case)
We’re also kicking off the new year at the Chapter with a couple of changes. You may have seen the notice that we’re lowering our monthly meeting ticket prices by $5. Another smaller change: We’re upping the ante for whoever writes the summary of the meeting for publication on our website. Now, once the article is published, the author receives a free meeting coupon. I hope people take advantage of this because if there aren’t any takers, we don’t have a summary for those who couldn’t join.
Speaking of remote folks, I know that many of you ask about recordings or streamed meetings. We tried last year, but there were too many technical and audio issues. If we get a volunteer who can devote more time to this, we promise to try it again!


In the spirit of the season, I wanted to share a couple of resolutions.
Drink more tea. This is really “drink more water” but disguised in Egyptian Licorice and other earthy flavors.
Do less harm. I’ve been thinking about how much my food and other purchases have an effect on myself and the environment, so I want to re-consider what I buy.
Meditate more. Taking a couple minutes to slow down seems so difficult, but mindfulness can be a powerful force in your life.
Keep challenging myself. Whether at work, training for a race, or fitting more yoga into my life, I want to keep pushing to do the best I can. I’ve found that I accomplish much more than I ever thought I would by having confidence in myself.
I hope you resolve to come to more Chapter meetings in 2016!