Bridging the Gap Between Trailhead and a Salesforce Career

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There’s something remarkable about Salesforce and its ecosystem of partners and end-users. Although Inc. is an enterprise software company, it successfully advocates equality throughout its ecosystem and takes strides to overcome typical barriers to entry that stand between individuals and technology careers.

Salesforce have launched learning tools (namely Trailhead) to democratize access to its technology, to enable individuals to upskill, and in turn, increase the number of Salesforce certified professionals. While Salesforce’s drive and outreach makes it unique, it is a huge undertaking that will take time to change, therefore, barriers can still exist.

PepUp Tech

Salesforce are not alone in driving inclusivity in its job market. Many people would have heard of PepUp Tech, an organisation whose mission is to “give motivated, underserved students the access, skills, mentors” – in other words, supporting individuals from underserved communities get their foot on the first rung of the Salesforce ‘career ladder’.

I was fortunate to sit down with Selina Suarez, co-founder of PepUp Tech, long-serving Salesforce Admin, and equal opportunities advocate. The topics we discussed during our chat include how Salesforce lowers barriers to entry with self-learning, the gaps between learning and practical application, and a new stream of talent coming into the Salesforce ecosystem thanks to a PepUp Tech program that she is spearheading in response to the mass unemployment.

This is part 1, where we cover bridging the gaps between learning and practical application of Salesforce for new Trailblazers. Part 2 will look into the new Salesforce talent stream that could fulfil the demand for Salesforce professionals that is currently outstripping supply, especially those with expertise from other industries.

As well as an inspiring story about finding unexpected opportunity in the crisis, she provided valuable insights that I bet will help and reassure many readers who are looking to jump over the first hurdle towards gaining real-world experience.

Note: This was filmed during the COVID-19 pandemic, and therefore some references are to that period.

Salesforce Lowers Barriers to Entry – Self-Learning as an Equalizer

Selina shares her story coming into the Salesforce ecosystem through the common ‘accidental Admin’ route 11 years ago. Early on in her career, she found her passion in Ed-Tech and nonprofit spheres; her first encounter with Salesforce was working for a nonprofit who supported students applying to college, but who were also the first generation in their family to apply. Her time working on improving the organization’s reporting and assessment metrics stayed with her – and eventually became the PepUp Tech mission.


“What you’ve said about technology being such a great equalizer is so true. If you are motivated and a self-starter, then you can harness that and drive your career. There’s that saying related to getting into certain industries: “it’s not what you know, but who you know”. I think in Salesforce, it’s the other way round, it’s not who you know necessarily, it’s what you know and what you can do with that.“

Trailhead Updated in Real-time


“Self-learning is great. Trailhead has made it a lot easier for us to teach at PepUp Tech because it’s so organized and they’re constantly improving it to match what’s in the Salesforce releases.

Back in the days before Trailhead, we had the workbooks, which always match what was in Salesforce, right? As the platform was updated, the book was not printed as quickly as the the three major releases a year. So Trailhead has been that equalizer from the technology stack perspective, when we’re thinking about access.“

Business Use Cases with Superbadges


“Trailhead is a lot of fun and it’s beneficial but without industry context, it’s hard to take it as far as you really can.
We use Trailhead in our courses, so I’ve been monitoring very closely how Trailhead has improved over the past couple of years.

I’m really excited about Trailhead Superbadges, which give you a good idea of how Salesforce is used in real business scenarios, very similar to what you would encounter in the real world – so that’s helping people.“

Hurdles Exist: Gap Between Self-Learning and Getting Practical Experience


“Although we’ve just spoken about how many great Salesforce-based initiatives are going on, there are still, sometimes, hurdles that exist – the ones that everyone’s working hard to get across.

But we are working with business-critical technology, so it’s understandable that some organization may be nervous about letting people who may have just come into the ecosystem, or just trained, to work on their CRM if there’s no accountability (no supervision from a skilled mentor).

There are obviously other barriers as well, like the cost of certifications and the cost of classrooom training (which, no doubt, is a great benefit to have on top of self-learning, – these both come at a price!

While Trailhead and all these self-learning tools are great (don’t get me wrong!) there is a gap between mastering Trailhead/self-learning, and actually getting your first Salesforce experience.

Is this a challenge that you see too and what would your advice be for someone at that stage?“

Find Mentor to Help with Context


“Definitely. It’s very expensive to get guidance. People like me and you, and others in the ecosystem, have tech context.

When it comes to access, it’s really hard for new learners who live in communities where there isn’t a huge tech industry; the underrepresented populations that we serve are not connected to that industry.

Even though they might find Trailhead, they don’t know anybody who can add context that’s understandable to them, which they will need in order to navigate through Trailhead.

It’s about examples. Sometimes when I’m in Trailhead, there’s an example of a company like a solar energy company. Some of our students don’t know what the heck that is! So, that example doesn’t work for them because they live in urban environments and they’re not attaching things to their roofs.

What we do is go through the Trailhead and we’ll talk to them a little bit about the solar industry, then we give them examples that they can understand…that are familiar to them in their communities.

If you are new and you needed that one on one instructor, somebody who was well-versed in the industry, you would either have to know someone who worked in the industry for a long time, which many of our students, they don’t have“ [which PepUp Tech provides].

Trailhead ‘à la carte’ – Knowing What you Need to Know


“Trailhead was created to be that ‘a la carte’, to pick and choose what you want to learn.

That’s great for people, like us, who have been in the ecosystem for a long time and we know what we want to learn. We’re like: ‘well I need to create some email templates. Let me go to Trailhead and figure out how to create this template.’ When you’re a new learner, and you are brand new to Salesforce, that’s a lot harder to do because you don’t know what you need to do.

A lot of questions that I get from people who are trying to train up on Trailhead are along the lines of: ‘can you point me to a Trailmix? Admin Beginners – should I take this trail?’ They’re confused about where to start and go. Trailhead has so much content that it can be very overwhelming for a new user who is not experienced in Salesforce.“


“Things that we take for granted, even knowing the difference between an Admin trail and a Developer trail.”

Pushing Through Overwhelm and Roadblocks


“Salesforce is a very complex tool – there’s a lot that you can do with it.
No one knows everything, right? (well, maybe Steve Mo, maybe he knows everything) But the rest of us are still learning, right? New learners do get overwhelmed when they hit a roadblock, they’re like, ‘well maybe this is not for me’.

I share my own experience because I’m an Admin, right? I’ve been customizing and building on Salesforce for 11 years, but I still have to go online and Google things and read documentation and take Trailheads.

So it requires you to make that commitment to continue to push yourself forward. We’re an industry that is characterized by rapid innovation. So I tell the students, it’s not that you don’t know it, it’s that the industry continues to innovate and you’ve just got to keep your skill sets moving forward.

The most important thing for you is to know where to go, when you stumble and hit a roadblock, because you will hit roadblocks. Good Admins like to solve puzzles and are curious, they read and research – these are the messages that we push.“

The Billboard Message


“If you could write one thing on a billboard, to broadcast a message to thousands of people, what would it be? It could be a messages for professionals inside the ecosystem. It could be a message to underserved populations or just the general public – and it doesn’t have to be Salesforce related. What would you put?”


“So Christina Jones, who works at Salesforce, sits on our board and she’s an incredible person who invests her career in helping organizations use the power of storytelling to share what they’re doing in the universe.

She encouraged me to think about what PepUp Tech is – are we just a training program or are we doing something that’s bigger than just teaching Salesforce?

They came up with the hashtag #FutureIsNow. If I had to blast anything on a billboard, it would be “the future is now” because it’s really true – the future is not tomorrow. It’s not next week. It’s not in five years, it’s today. What are you going to do today to get to where you want to be?

Next Steps: How can you find out more about PepUp Tech?

“We’re always looking for volunteers. So anybody in the Salesforce community and beyond, who wants to take what they’re doing in their business and teach others. We’re doing 1500 students this year that would love to hear from you. You can come speak, you can guest teach, you can mentor a student, you can assist them on a coaching assignment.

Stephanie Herrera, who is one of our founders, has a number one thing to get PepUp tech global, so that people in London and Amsterdam and Paris where our other Salesforce Saturdays communities live can have access to this program as well. If you are in another country and you want to apply to our programs, they are open for you to apply.“

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