May 6, 2019

How Dropbox is Creating a Data-Driven People Culture


In today’s fast-growing tech companies, you need leaders who can make informed, unbiased decisions quickly - especially when it comes to decisions about people and culture.  

So how do you do that?

I sat down to speak with David Gainsboro, People Data Analyst at Dropbox, to learn how.

I first came across David’s work when I happened upon his presentation from the 2018 People Analytics and the Future of Work conference. His talk, titled “Before and After Self-Service Analytics,” showcased some of the ground-breaking work that Dropbox is doing to ensure its teams can access, understand, and act on People Data.

Marrying People Analytics with a Customer-Centric Approach

As a People Data Analyst, David believes that it’s not enough to generate and share data with your internal team. You have to make the data usable. It has to be timely, relevant, and understandable - even by those who are not data-savvy.

David’s philosophy towards people data is informed by his journey into the field. He studied sociology as an undergrad (woot!) and later moved into technical roles within mid-market and enterprise sales teams - first at Varonis and then at Dropbox. At a certain point in his career, his passion for serving customers and creating meaningful change for people converged.

Here’s how David describes his journey:  

“A lot of people think of sales as a transactional experience. At Dropbox, it’s more collaborative. We want to know how existing users leverage Dropbox and how we can make that experience more productive and more secure. I did that for a couple of years and towards the end of that time, I wanted to push myself technically, so I took a class in C and Python and found that I really liked working in R.

I also started Dropbox’s first LGBTQ Employee Resource Group called PrideBox. It’s been a great chance to give back, build community, and make sure the voices of the LGBTQ community are heard within Dropbox.

When a new role opened up on our People Analytics team and I realized that I could have the opportunity to advocate for inclusion and equality, create customer-centric products, and build my technical skills.  I applied for the position and the team took a chance on me. It’s been a great opportunity and I’ve learned a lot since then.”

The need for good data AND data literacy


David sees two main challenges in the People Analytics field right now - the need for good data and the need for data-literacy amongst managers, recruiters, HRBPs, execs, and L&D teams.

David says “It’s not enough just to provide your teams with data on you teams. You have to provide insights in addition to the numbers to make sure the lay person can understand what you mean. Data cannot exist in a vacuum and a few numbers can’t provide teams with answers to questions about external hiring, reorganization, or even performance.”

We also get really excited about thinking about analytics. As analysts, we launch all these dashboards - but we need to also look at usage patterns. What do my users need to know to understand this data? What do users need to know to put it into action?”

Making data understandable and actionable

Dropbox’s initiatives to increase data literacy amongst its leaders and teams is impressive. They started first with a solid understanding of their org’s needs.

David explains:

“About a year ago, we kicked off a data literacy gap analysis across HR. We asked our teams questions like, ‘What is a good analysis from your perspective?’ ‘How do you use data on a regular basis?’ ‘What is your understanding of the data we provide?’


“We found that there was a huge range in data literacy. We had people who were quite sophisticated and wanted to know how to build a narrative and create a plan for shifting people data. We also had people who were having trouble just logging into Tableau.”

“From this data, we created a data literacy program - starting from baseline knowledge about how to access our data tools and then understanding key metrics. For key metrics, we asked people, ‘What are the vital signs for your team or for your job, in Recruiting?’ Just like a doctor, everyone at Dropbox needs to know the health of their teams. This was a very helpful framework for everyone.

“We also gave them tools on how to understand the data and tell a story with it. We taught them how to create root cause analysis and shared a template that teams can use to troubleshoot future issues.”

A Data-Driven Culture = A Happy Culture

Dropbox is a phenomenal example of what a data-driven culture looks like at scale. With more than 1800 employees globally, the company has invested heavily in giving its leaders the means to understand and act on the indicators that lead to a productive and engaged workforce.

As David says, “The talent market is tough right now. It takes a lot of resources to hire the right people. We want to make sure that once people are hired, that they stay awhile. Investing in people analytics is about investing in understanding what makes people happy. It’s a key part of our culture and what makes Dropbox a fun and rewarding place to work.”

If you're interested in creating a data-driven people culture within your organization, reach out below to start a conversation.

Note: Images are courtesy of David and his colleague, Scott Walker.

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