From sales to sales enablement with Danny De Los Santos, Atlassian

SEC's Sales Enablement Innovation podcast is the place to be when it comes to enablement knowledge-sharing.

Every episode features an enablement expert sharing their stories so that you can learn from their experiences in the field.

Here, check out the highlights from our conversation with Danny De Los Santos, Senior Team Lead for Curriculum, Strategy, and Training at Atlassian. Danny took us through his own journey from sales to sales enablement.

He shared his thoughts on sales enablement in a digital age and the challenges associated with this change. He answered our questions about best practice tips and industry stories, his owm podcast and the unique challenges that are part of such multifaceted roles.

While we've got the highlights right here, for the full episode simply click below and enjoy all the insights. 👇

Q: Tell us about your background, how did you end up in sales enablement?

A: I've been in sales enablement since 2016. Prior to sales enablement I was also an account executive (AE) for a couple of years, as well as being an enterprise sales development rep and also working in digital marketing.

So I had a background in marketing, sales, sales development, and then made the shift to sales enablement at Cloudera.

Q: What prompted you to make that shift?

A: I started my career in the nonprofit sector, and then started to work in technology shortly after that. My first couple years in tech, I was working at startups and Cloudera was one of the larger organizations I had ever worked at.

When I got there, I joined as an enterprise sales development rep and was in that role for about a year where I was tapped to do sales enablement.

I was someone who naturally was finding ways to help other new people, either on board or if I would get to my quota, I would then dedicate a lot more of my time to helping others get to their quota.

I was coaching, I was teaching people how to be productive, how to have great customer conversations, and how to navigate complexity within sales.

There was an opening that came up on the sales enablement team and leadership came to me with the offer. At that point, I wasn't sure if I was going to actually like sales enablement.

I think one of the harder things about going into sales enablement, especially from a sales role, is the really big mindset shift.

In a sales role, you have a quota while being in a sales enablement role you don't have that quota comp structure. A lot of the problems involve more critical thinking and more strategy. It was something that I wasn't sure was going to be for me.

Q: Do you think that the fact you've worked in sales means you understand the salesperson mentality?

A: Absolutely. I think empathy is so important in this role because our job is a sales support role, we're here to support the generation and drive the amount of revenue the company is able to generate through sales.

I think this is a common scenario which many companies find themselves in, where marketing will develop a asset, a piece of collateral, a job aid, a messaging talk track, and sales will be like “yeah, that's not how it goes in real life, a customer would never respond to this”, or “this still doesn't really address the root of the pain that customers feel”.

Because I came up through a sales and marketing role, I do feel like that gave me the ability to empathize and feel what our sales people would expect to feel if they were presented with a piece of information.

Then ultimately, I became an advocate for our sales teams and I think that's an important part of the sales enablement role. It's not just training, it's equal parts programme and project management alongside that.

As sales enablement professionals, we need to advocate and be the voice for the field when they're not present in organizational meetings.

Q: Atlassian has a well-structured and established sales enablement function. Is this something recent?

A: Sales in general, is something that Atlassian is continuing to invest in and scale. If you're familiar with the Atlassian model (if not, you can Google ‘Atlassian flywheel’), a lot of the selling motion at Atlassian had been self service.

But as we continue to scale across the enterprise and deliver value to our customers at the enterprise level, that comes with a traditional selling org. If people are investing $100,000 or more in our product, they want to have a human element to it. Atlassian understood that and decided to invest in a sales org.

We're continuously growing and evolving, there's days where being at Atlassian can feel a little bit like a startup, because on the outside, we could appear as a very mature structured organization, but internally, we're still scaling and evolving and which is super exciting.

It's a great time to be at Atlassian, because of that level of involvement and impact and visibility you can have in the organization.

One of the things I like about Atlassian is their commitment to people and developing people. The business has realized the impact and value of sales enablement. and so they've staffed us accordingly to invest in our people.

I think it’s really telling of the quality and culture of working at a company like Atlassian.

Q: Could you give us an overview of how you work together with different teams?

A: We have structure and process, but it's something that’s continuously evolving. Over the course of the year, I've seen this really improve the level of partnership between us and Product Marketing, as well as product teams.

The way we're starting to think about launches and major initiatives hitting our customers, we are continuously getting better and ahead of the curve.

But it wasn’t always that way.

I think part of that had to be because every sales enablement team at every company (especially if you're if sales enablement is a new discipline that the company is just investing in)  has to scale your resources accordingly and show the value that sales enablement gives to an organization.

And so I think what we've had to do is show that when you bring enablement in early, and when enablement has the proper time and scope to think things through, the end product of our enablement is so impactful.

But there were definitely growing pains there of people understanding we're intentional and oftentimes, people forget that sales enablement professionals are there because a part of their job is to understand adult learning and best practices.

We are the representation for our audiences for our constituents and we know what they're going to respond to and what they're not going to respond to. And by engaging us early, we're able to drive that kind of impact.

Q: As part of your programme, you now use podcasts. How do you use that as a sales enablement tool?

A: I’ve always had a passion for blogging. I was a journalism major in college, and I dabbled in trying to have my own foodie blog and my own foodie podcasts.

A teammate of mine had an idea and said to me “Hey, you know, wouldn't it be cool if we started a podcast?”, and it was right when the pandemic hit. I remember thinking, “we're so sick of Zoom, I'm on Zoom for eight to 12 hours a day, Zoom now means work”.

And so I said “Yeah, let's try out a podcast.”

We knew that we wanted it to be short, informative, educational, entertaining. There's this notion of ‘edutainment’ that I joke around with the team that we need to make our enablement entertaining, educational and entertaining.

We planned it, scoped it, and presented it to leadership so that we could go and purchase plug-in mics to our laptop and some editing software to make it as professional as we could.

We invite technical experts, usually the sales engineers, to be our guests. My colleague, and I co-host the podcast, we'll do an interview, and then we'll edit out the 10 minutes worth of the most important information, package that and send it out to the field.

We try to keep it humorous, but at the same time, we tried to go deep for 10 minutes into a technical concept. And it's been really fun. We have a spin off podcast series called The Deal Download. Anytime we close a great deal, we ask our seller three questions (so each episode is maybe five minutes): “What was the business problem? What moved the needle? And what did you learn, or what would you have done differently in this deal”.

AEs love learning from one another and it's also great for marketing to hear how we're winning deals, how our customers are responding, and what actually is moving the needle.

We're starting to see that podcasting is a great way for people to learn and why we're going to continue investing, growing and scaling our own little podcast network.

Q: Do you have any predictions or a vision of how you would see sales enablement at Atlassian?

A: Months feel like years at Atlassian, in the sense of what I was worried about last month, feels like so long ago - I don't think that's unique to Atlassian.

The global markets and the companies that needed to adapt their way of working, in lieu of a pandemic, created a difference in how customers are now buying. People are expecting to go through a sales process without ever having to meet their account executive face to face in a boardroom, that is all virtual.

I think we're going to get to a point where we're gonna need to find different ways to start enabling, because what's relevant today might not be relevant in a quarter or six months from now.

It’s important you’re not putting all your eggs into one massive training you're hoping is going to get you through the rest of the year on a specific product line.

You have to break it up into consumable chunks so that not only can learners absorb that in this new ‘remote work’ culture we're in, but also to make sure that you're continuing to remain agile to the needs of the business.

In two years time, we could still be in a heavily remote culture where things are continuing to shift and we want to make sure that we as an enablement team are being agile, and we're making sure that we can be responsive to the needs of the business but also proactive and always thinking ahead.

Q: If you had to give one piece of advice to someone who is looking to transition into sales enablement, what would it be?

A: What I would say is if you are in a sales role, and you want to get into sales enablement, or even if you're in a marketing role, and you want to get into sales enablement, I would recommend starting to take on stretch goals.

I am a big advocate for this strategy because it worked for me and several people who got hired onto my team, as we promoted them internally.

If you're in an individual contributor role, especially if you're in a sales role, start thinking about what you can do today to help your sales enablement person at your job.

If you don't have a sales enablement person, how can you start to take on some of that work on the side so that when the opportunity does come up, you already have experience to go for that opportunity.

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