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Career Life Stories: Dan Pupius, Range Labs

At a turning point in Dan Pupius’ life and career, Google serendipitously spotted his talent in an online community and wooed him half-way across the globe to Silicon Valley.

After several years at Google, he went on to lead Medium’s engineering department where he developed a passion for understanding the way companies are built and subsequently scale. Dan is now CEO of his own company, Range Labs.

What inspired you to pursue engineering as a career path and how did you get your start?

When I was in school I’d wanted to go into the space industry and was considering planetary sciences and astrophysics, but at the last minute ended up studying artificial intelligence because I was interested in robotics as an alternative path, then completed a master’s degree in industrial design.

In high-school, I was involved in some of the early online communities for programmers and picked up coding gigs on nights and weekends. That’s where I learned most of my practical programming skills.

After my studies, I worked in contract roles in e-learning and for a start-up in London, working nine months of the year; I’d spend winters snowboarding and part of the summer volunteering abroad.

I wasn’t enjoying contract work and made the decision to leave tech and move to Canada to be a ski photographer. I was preparing for a trip working in Honduras for the summer before my move to Canada, when I got a call from Google. I went through the interview process and received an offer literally the night before my departure to Honduras.

It turned out that Google had found me through one of the online communities. There was a group of us experimenting with DHTML – the precursor to AJAX and Web2.0 – pushing the limits of what was possible in the browser. I was lucky that with Gmail and Google Maps launched, this had become a very marketable skill. It was around 2005, and people from all over the world, who I’d never met in person but had known in message forums for years, all ended up working at Google at the same time.

Dan Pupius

How was the transition from a big company (Google) to a startup (Medium)?

I loved my time at Google. Going from dark and gloomy London to sunny California was amazing, and it was energizing to work on some amazing products used by millions of people. But towards the end of my time there, I became somewhat disillusioned with my ability to have an impact. I felt like a small cog in a very big machine.

I took a sabbatical, during which I met a lot of people. I was introduced to Ev Williams after his departure from Twitter, but I didn’t know that he was working on something new. I thought he might be able to give me advice about the landscape outside of Google, but it turned out he had just started a company with Jason Goldman and Biz Stone called Obvious Corporation, doing a combination of investment, incubation, and product development. It seemed like a really unique opportunity, particularly in the way they were approaching company building.

I joined the team at Medium in February 2012 when there were around 10 people and back when Medium was little more than a word on a whiteboard.

Which of your experiences as a young engineer best prepared you to lead engineering at Medium?

Watching what worked and didn’t work while at Google helped me a lot. But, honestly, very little from my engineering career prepared me for the role at Medium – leadership is a completely different craft and completely different set of skills. Though, I would argue that using an engineering mindset to navigate and solve managerial problems played to my advantage.

So much of engineering is about problem solving and systems design, and organizations are systems – they’re incredibly complex systems with lots of black boxes and hard to predict elements – but systems nevertheless.

One of the engineering principles I try to teach and practice is to learn from prior art: both your previous experiences and others’. That’s not to say you should be carbon copying everything, but there is often no need to reinvent the wheel.

Another experience that helped prepare me for leadership was running the base camp for an expedition in Honduras. It wasn’t an explicit position of authority, and I had to work with people from very different backgrounds and disciplines, so it ended off being a kind of servant-leadership.

Can you tell me a little bit about Range Labs and how it came about?

A lot of people feel that as companies get bigger they get worse. Bureaucracy creeps in, things slow down, and work becomes less fun. I don’t think that should be a universal law of nature.

Coaching and training can be hugely helpful in leveling up management and organizational practices, but they only get you so far. All too often the coaches leave the building and things go back to the way they were. Processes built on social norms can be fragile in the face of rapid change and growth – new people arrive, old people leave, people change roles. We saw the opportunity for a new type of software that provides structure and support for the habits and behaviors necessary to build and sustain a high-performance culture at scale.

We talked to people from dozens of companies, looking for a starting point. The common thread was that people didn’t know what was happening across the company and they felt disconnected from their teammates. So our first product is built to address these needs.

What challenges did you encounter while co-founding your company?

When you’re getting a company off the ground virtually everything is a challenge. We’re only 18 months in and are constantly learning. Looking back, fund raising went fairly smoothly, although at the time it felt very challenging.

I am a co-founder and the CEO, but I’m also the lead engineer; I need to replace myself in the engineering department, that’s my next big hurdle.

But, for the most part, as a founder you expect this journey to be a challenge. That’s what you signed up for.

What trends are you seeing develop within the field of engineering?

My primary observation, more so than trend, is that the rate of change within technology is increasing. It used to be that you acquired knowledge, and that knowledge served you throughout your career. Now it’s not what knowledge you have acquired, but how fast you are able to acquire new knowledge that will propel your career. The people who will succeed are those that are the most adaptable and can apply their learnings from different disciplines and technologies to new situations. It’s important to cultivate a growth mindset in yourself and others.

That said, and there’s a contradiction here, you can’t just dip your toes into the water on a hundred things – you have to master one discipline first. I like what Adam Savage said: that if you get really good at one thing, it makes getting good at other things easier. So I’d encourage people earlier in their career to go deep on something, but then not to stop there. Do the uncomfortable thing, branch out and do something different. Learn to learn.

What advice do you have for startups trying to recruit top engineering talent?

Start by asking what does this person need? What does this engineer want in their career? What do they want from their work environment? What can we provide?

Different companies can provide different things, just as different candidates will be looking for different things. You want to find a fit that works in both directions, and then target your recruiting process at the right people.

More generally, Daniel Pink’s book Drive resonates with what I’ve seen. Most candidates are looking for three things. First, they are looking for some kind of purpose and meaning. They want to enjoy what they’re working on and know that it matters – they want some connection with the company’s mission. Second, they want some level of autonomy and agency; most people don’t like being told exactly what to do, senior folks especially want a seat at the table, and want to be involved in decision making. And third, people are looking for growth – even senior people want to learn new skills and stretch themselves.

Assuming your company checks all these boxes, it then comes down to showing candidates that you’re able to provide those things. It’s somewhat easier if you can sit down with someone one-on-one, but the reality is that most engineers won’t pick up the phone if they don’t know who you are. This is why I think recruiting, especially recruiting engineers, is very much a marketing problem.

You’ve got to let candidates get a sense of the business and culture outside of the interview process. Blogging can be an authentic way to talk about yourself and/or your company. Meetups and speaking events are other ways to spread the word.

My opinion is that companies should think about recruitment as a process that’s constantly evolving. You have to approach talent acquisition like you approach product development – you have a goal, you have metrics, you have a process, you get feedback from customers (the candidates you did and didn’t hire), and then you optimize and revise.

What advice do you have for engineering candidates that are being recruited by multiple companies simultaneously? In your experience, what are some good ways for engineers to vet potential opportunities?

This is obviously a very personal decision, it really depends on what an individual is looking for and I’d be skeptical of anyone offering blanket advice. One person may be optimizing for learning and growth whereas another person is optimizing for cash compensation in order to pay off student loans or support their family. I don’t want to judge people on their decisions, but I do think there is a strong argument for optimizing for learning and growth early on in your career. The diversity of experiences you can acquire early in your career will compound and can accelerate it quite quickly.

With regard to vetting opportunities, make sure you’re talking to as many people at the company as possible. If you can, talk to alumni of the company as well. Why did they leave? What were the conditions? Always take those conversations with a pinch of salt, because of course everyone leaves for a reason, but I think the alumni community can be a very valuable place to start.

Do you have any go-to engineering resources that you’d recommend to other engineers? (e.g. blogs, books, podcasts, conferences, courses, etc.)

For engineering resources, I just Google a lot to be honest; I often have 20 tabs open at once, and I think the ability to track down and validate information is a skill worth developing.

Right now, I’m mostly focused on finding resources about organizational design, psychology, and management. For these topics, I read a lot, listen to books on audible, and attend meetups. But because leadership is as much about understanding your own personal psychology as the psychology of others, there’s only so much you can learn from books, so I value coaching and leadership development programs. I like programs that favor experiential learning which can fast-track this personal discovery. I especially like Pathwise Leadership which I’ve been participating in for several years. I’m also a mentor at Plato, which is a good resource for new managers.

Also, for Bay Area folks, the San Francisco Engineering Leadership Community is a good group to check out.

Finally, what is the best way for readers to connect with you?

You can follow me on Medium. To find out more about Range Labs you can visit our website. If you’d like to connect with me personally, you can add me on LinkedIn. If you do connect, please leave a message about what you want to talk about, as I get a lot of spam.