Dan Dreams of Coding

Anyone who knows me knows that I’m not, shall we say, fashion forward. Or fashion anything, really. My tastes run towards jeans and black hoodies, mostly so that I never have to think about what I’m going to wear. So, it’s come as a bit of shock to friends, family, and colleagues that I’ve taken a role as CTO for an e-commerce site specializing in luxury Italian footwear.

The conversation usually goes something like this:

“Wait, what? Back up a second. You left TripAdvisor? Again? And… Italian shoes? Um… (concerned look) Who are you and what have you done with the real Dan?”

So yes, I had a great time at Trip, learned a tremendous amount, went through some pretty intense and exciting projects, and ultimately was ready to move on to something new. Definitely some blog posts in there, perhaps for another time.

“OK, but… shoes?”

Fair enough. And, in fact, that was my first reaction too. When I first learned about the opportunity, I looked at the website, wrote an email to the recruiter saying I wasn’t interested in fashion, moved my mouse to click the send button, and… didn’t. Instead, I got curious. How was this (as the recruiter had assured me) one of the hot up-and-coming Boston startups?

As a software engineer in a major market like Boston, you have a fair amount of choice. Quite aside from the question of who might make you an offer, how do you sift through the options?

The first point was that I wanted to do work that would make the world a little better. A lot of the work at TripAdvisor boiled down to optimizing conversion rates on landing pages, but that didn’t change the fact that the company’s goal was to help people enjoy their lives more. It wasn’t curing cancer, but I always felt we were on the positive side of the ledger. When I started digging into M.Gemi, I discovered that a significant part of the story was how they’d built relationships with struggling family-run factories in Italy, and were helping them get back on their feet after much of the shoe manufacturing industry had moved elsewhere (by contrast, other brands sometimes manufacture in lower-cost countries, then do the final stitch in Italy so that they can claim “Made in Italy”).

I also wanted to choose a winner. I’d been passionate about HelloShopper, had been a big user, had thought the idea could win… But we’d never figured out how to build our customer base, and the company had died. I didn’t want to live through that again. The contrast with M.Gemi, though, was night and day. M.Gemi’s founders were serial entrepreneurs who’d founded Lids and Rue La La, and after only four years the site’s annual revenue was on a great trajectory. These were highly credible people, who’d had a ton of success in the past, and were already seeing impressive traction.

But what about technology? They already had a site, it was making a ton of money, and – to be blunt – e-commerce wasn’t exactly cutting-edge. Were they only looking for a team to maintain and optimize their existing site? I needn’t have worried – as it happened, their near-term business objectives involved a complete re-platforming. Their current e-commerce platform had an onerous rev-share that hadn’t mattered when they were small, but was becoming increasingly painful as revenue hockeysticked. Far from being resistant, they were champing at the bit to move to something more performant, scalable, and reasonably priced. Combine this with an interesting data science angle, and there was a huge opportunity to do a lot of fun, challenging technical work.

Culture and workplace sanity ended up being my biggest concern. I’ve worked at some pretty unhealthy places, particularly back when I was in the video game industry, and had no desire to come in to work every day to a David Lynch (or Mike Judge) movie. I wanted to work with capable, sane, kind, smart, tough coworkers, and for the problems we faced to be irreducible business problems, not the self-inflicted results of people acting in bad faith. I wanted to be able to learn from my peers and leaders, to hold and be held accountable, and to share a high level of respect and trust. Glassdoor was one data point, but not a great one – there were only a handful of reviews, many weren’t flattering, and it was hard to judge how much weight to give it. Wanting to get more of a random sample, I reached out to a number of past employees – some of whom I knew, some not. I also dug for information throughout the interview process, pushed my interviewers on a number of issues, and asked the same questions of different people to see how their answers compared.

What I experienced at the time, and have since confirmed, was an extremely open, friendly, and direct company culture. All company numbers – successes and failures – are shared at the weekly company meeting. People genuinely seem to enjoy each other’s company. And importantly, there’s a culture of radical candor – when people disagree, they don’t hold it inside. The style is different from what I’d known at TripAdvisor, and in the end I think it suits me better – more relaxed, more open, just as direct, but less Vulcan.

A number of people left the engineering team over the past year, which now needs to be rebuilt from a small base. This is one of my biggest challenges, and also one of the things I’m most excited about – here’s the chance to build an amazing team, and engineering culture, almost from scratch; to build in diversity and a heterogeneous skill set from the beginning; to optimize for team IQ and effectiveness; to build a learning organization, in which everyone has an area of expertise in which they can mentor the rest of the team.

When I first joined TripAdvisor, I didn’t know much about the travel industry, but I learned. And while it’s true that I know next to nothing about fashion, I’m learning. I’m also learning about supply chains, warehouses, shipping, returns, exchanges, customs, physical retail, inventory, and order management. I’ve always tried to optimize my career for learning (even when going back to Trip for round two), and I can feel my brain bursting at the seams with all the new information I’m trying to cram in. So yes, Italian shoes. It’s a great place to be.

Speaking of which, I’m building an amazing team. If you’re interested in learning more, I’d love to talk to you! Please send me an email at daniel@[M.Gemi’s domain here], and let’s get started!

Thanks! I hope to talk to you soon.