Dave O’Flanagan is CEO and Co-founder of Dublin-based Boxever. The company helps airlines such as Emirates, Aer Lingus, and Air New Zealand along with low-cost carriers like VivaAerobus leverage customer data to offer a more personalized experience for travelers. 

This is Dave’s first CEO role. He gave some sage wisdom about the tipping points in a start-up, the role of HR, how product professionals can become good founder CEOs, and the mindset of millennials.

Boxever CEO Dave O’FLanagan

When you were starting out in your career, what did you think you wanted to be?

Ah, I wanted to be a pilot when I was a really young kid. I wear glasses and in Ireland at the time you needed to have perfect eyesight. Growing up I was the nerd in school. I studied math at university and I was always into computers.

I started out in the telecoms industry where I worked as a software consultant for a number of years in the analytics space for mobile telcos worldwide. We were looking at helping those guys analyze all call records and making sure everybody got billed correctly. We also did marketing analytics answering questions such as: Who are your high-value customers? Who spent the least in network? Who is making the most calls? We exited that business in 2007, and I moved to an airline e-commerce company here in Dublin. We did e-commerce functionality for big airlines around world, such as JetBlue, United, and Delta.

What I saw in that industry was really big organizations struggling with building direct to consumer relationships. Most airlines always sold flights through intermediaries like a travel agency or a tour management company, which held the relationship with the customer. If you were not in an airline’s loyalty program, you kind of didn’t exist.

With the advent of e-commerce and direct to consumer digital programs, most airlines are still struggling to build relationships with customers. Most airlines don’t have a fully functioning CRM outside of loyalty programs. They struggle with connecting the dots across silos that contain customer data. They want to understand 1) who their customer is and 2) how to best serve that customer in the channel whether it’s on their web site, in the airport, on the airplane, via the call center, etc. I saw this firsthand in some really big airlines globally, so I started Boxever in 2011 with some top guys from my old company. We began this journey to solve this really big problem.

So I never set out to be a CEO. I wanted to build a really great product and sell to exciting brands around world. I wanted to do something that made a difference and help these organizations deliver a step change in their businesses. It happened that I became the CEO at the start. We’ve grown from three guys in a garage to almost 70 in Dublin working with airlines all over world.

When you were starting out, did you all think about bringing in someone else as CEO? How did that happen?

I was an executive in my previous company managing a large number of engineering and product guys. I enjoy leadership. As Boxever grew I grew. When we were just three guys we were writing code and hustling to get our first customer and raise our first round. As the company has grown we’ve developed parts of the organization, and I’ve grown into the CEO role. I don’t think it was ever any intention to bring in someone else. In the early stages for tech co-founders it’s common to bring in a sales guy as CEO to build the company. However, nothing trumps passion for your product and the company you are trying to build. At an early stage that is what the CEO role is all about. To get early commercial traction, you must ensure that you’ve got a product market fit and inspire people to join your cause. I was always really excited about doing that. It’s been a great few years building this organization.

Your road is probably the most common at least in the tech start-up arena: A product type person starts a company. If you were advising a product person who wants to start a company, what experiences would you encourage them to have to tackle the CEO role? 

It depends on the type of company you want to build. What product people need but may not get is having commercial exposure to sales and marketing as well as understanding what it takes to actually bring a product to market. Usually, product people are more focused on the road map and developing specific parts of a product, etc.

Product managers on the other hand are almost acting as VPs or mini-CEOs: They connect their potential customers with a need and build a product to fulfill that. Sales guys are experienced in delivering commercial value to customers. So product and sales are two great areas that CEOs can come from.

In terms of what a product person might need, as the company scales beyond a few people, you should think about hiring capabilities that you may not have yourself. At least initially you should have some exposure to different functions such as finance, marketing, and sales, so that when you start a business you can fulfill those. In a tech start-up the CEO does nearly everything at first. If you are up for that and it excites you, then a product person would be suited to that role.

You mentioned growing into the CEO role: Are there any specific things you did to gain knowledge and develop in the CEO role?

Early on, I found myself some mentors. Those guys helped me identify my blind spots. They’ve been through scaling high-growth companies and some had successful exists. They helped me understand how to interface with investors and engage with VCs. They also helped me discover some potholes in my plans in terms of sales and marketing.

So one of the things I recommend to any entrepreneur starting out is to try to find mentors or advisors who can help you pinpoint your weak spots. As your company scales, you need to learn to solve those or bring in experienced people to cover areas where you might not be as strong. For product CEOs, it might be operational experience. For CEOs with a tech background, it might be sales and vice versa. It depends on who you are and where you come from. Have a mentor early on was hugely impactful in making Boxever a success.

As you’ve transitioned from three folks in a garage to 70 employees, have you noticed any tipping points, where you had to think about how to run the business differently?

Yes, when you go from three to 10 it changes slightly. When you get to 20 it’s kind of a tipping point, where you probably won’t have close personal relationships with everyone anymore. You start to think about how to communicate and engage with the rest of the company. As the CEO you wonder: Does everyone understand the vision and mission? Are they aligned?

As you grow these things become harder. You need to give more thought to how you communicate. You don’t always get it right. As you scale maybe you realize all the sales employees aren’t on message anymore. They are all interpreting the Boxever mission and vision differently. So going from zero to 20 is one journey. From 20 to 50 is another one, and 50-200 is another scale challenge. We’re on that journey at the moment. We make mistakes, and hopefully I’ve learned to try to minimize the impact as best I can and grow from there.

As you stated, at 20 employees you had a personal relationship with everyone and could get information directly from each person. Now that you are at 70 people, have you had to change how you get information from everyone in the organization?

I know that 70 employees isn’t that big in the grand scheme of things. I still feel connected to everybody. It’s important that there’s a two-way communications structure in place that allows us to scale. That’s the biggest thing about going from 10 to 70 people. You have to start putting in structures and processes in departments. We didn’t have departments at 20 people. As Boxever has evolved we’ve got departments such as product development, engineering, sales, marketing, HR, and an experienced leadership team to build those organizations. They work with teams and ladder up communications through the business. We also have weekly leadership meetings and bi-weekly town halls. We use different communications platforms that allow us to get messages in and across departments, and we work with our HR team (what we call People Operations) to ensure we are listening effectively.

Our position ultimately is that we help these big organizations create engaging, powerful customer experiences. In People Operations we are creating engaging and powerful employee experiences internally. The ongoing thing that we’re constantly striving to improve is analysis around our internal communications. For example, are our people hearing what we’re saying? You can’t underestimate how difficult it is to consume all this information. We are constantly asking ourselves: Should there be more video than text? Should we have more face-to-face or less face-to-face time? We continuously reiterate and challenge ourselves how to best interface with employees and teams so that everybody understands where we are and where we’re going.

How do you think about the role of HR in your organization?

We only brought in HR over the last eight months. To me it’s had a dramatic impact. The most expensive thing in a tech company is the people. You spend huge amounts of money on tools and infrastructure and things like that. But it’s the people who make this company. Investment in HR has probably been the most transformative thing in our business. It’s been incredibly important for guiding us in how we acquire and manage talent, identify high performers, give them opportunities to grow, training, etc. In hindsight, I would have invested in HR much earlier.

Say a new employee comes in and asks, “Hey Dave, what do you do here?” How do you give the executive summary of the CEO job?

I do three things: 1) I make sure the company is funded. 2) I try hire the best people I can and inspire my team to hire the best. 3) I make sure everyone understands the mission and vision of Boxever.

If I do those three things really clearly and enable my leadership team to do that for their teams, then we’ll have a business that can function and exceed expectations. There are a lot of other details, but if I can do those three things really well, I believe the people I hire can go execute that, and we can do great things.

On a day-to-day basis I do a host of other things. I’m heavily involved in operations issues and in sales. Boxever has lots of big customers – everyone from Emirates to Air New Zealand. Those guys want to meet the CEO from time to time. My role outside of the three big objectives is being the face of Boxever commercially. If we are doing some big strategic work with an airline, I typically get involved as well. That excites me. I love being in the room seeing how our product helps them and how we can move their businesses forward.

There’s a lot of talk in the U.S. in management circles about the millennial generation. Is there much talk about that much in Ireland? Is there a difference from a management perspective?

It’s interesting, there is lots of discussion about millennials and how entitled they are. As a tech company we’ve got a blend of experienced and younger employees. My feeling is that millennials are super engaged and really want to work for a company with purpose. They want to believe in what they’re doing. It’s not about money although money is a factor. It’s really about, can you create an environment for those guys to feel like they make a difference? I don’t want to be facetious and say that’s all they’re thinking about. All the younger employees we have here are tremendously hard working and engaged. They are doing things that are more than I would have expected in terms of their experience.

For me, I don’t think it’s just millennials. Everybody wants to believe that what they’re doing is making a difference. For me whether its millennials or a little bit older, it’s making sure everyone knows why Boxever exists and believes their daily work helps us move the needle forward. If we can create that platform for our employees, it builds a great culture and sense of getting stuff done. We don’t really discriminate in terms of age or experience. It’s about, can this person do the job? Will they grow into a role? Are they excited about being here? Are they a fit with our culture? If that’s the case then we’re super excited about having them on the team.