A year ago last Friday I left eight years cutting code and plumbing servers to take my very first marketing job. Prior to then and even before in college and high school, hard skills were what paid my bills – technical work building stuff mostly for the Internet. Everything I had done up until last year required only the soft skills needed to send a group email or interview a candidate, certainly a pittance to those required to craft a message and get it in front of an audience.

I knew I needed more than that. While I was at Boxee working for Avner Ronen I made the determination that I wanted the CEO role for my startup. Like a lot of folks who spend their career in the high risk, high reward, high laughs world of early stage tech, I’ve long held my own entrepreneurial ambitions, but after working for a programmer-turned-head-honcho, I came around to the notion I could make a greater contribution to that endeavor by pushing the vision and the culture rather than the technology and architecture. I didn’t want to be the technical co-founder – I wanted to run the circus.

But, I was sorely deficient. Sales and marketing were skills I just didn’t have and were I to ask others to entrust their livelihoods and their families in such an enterprise, it would be incumbent upon me to learn. To do such a thing with a knowledge base very nearly zero would just be irresponsible.

So, to get some of those skills while keeping my technical chops up, I hopped onboard Twilio as a developer evangelist. Like a lot of companies, Twilio’s devangelism program is under the marketing aegis and the gig meant working for one of the best marketers I knew. I’d still write code, but would do so surrounded by the thoroughly unfamiliar context of message craft and story telling. And through the daily demands of the job and the proximity of those who do it well hopefully I’d learn a thing or two about this marketing thing and ultimately serve those I wish to lead better.

Holy biscuits – did I learn plenty. A year in, I thought it might be helpful to my fellow developers to share what it’s like to turn to the Dark Side and what I picked up in the process.

1) This Shit Is Hard

Like many folks who build stuff, my disdain for marketing as a business discipline had grown ironclad. I thought soft skills meant it was a soft job – 9 to 5 without pagers ringing, apocalyptic deadlines or material consequences for poor workmanship. A marketer was never around when I had to get a server back up or the prod db was borked; this gig must be easy.

I learned swiftly that this view was as legitimate as assuming web development is easy after installing a Squarespace theme. My view (and likely yours) was informed mostly by bad marketing, which is every bit as prevalent as bad programming. Install ten WordPress plugins and base a view on software engineering and I’m sure the 7 out of 10 bad experiences one would encounter would foster a belief that the entire discipline is bankrupt.

As it turns out, the ones who do it well are rare and far less visible because – like good programmers – their work is a lot harder to notice. Good marketing is a product of the same inputs as good code; long hours, sweating the details, and the judicious application of experience doing it the right way.

2) Data Wins Arguments

When debating the performance of a chunk of code or a particular architectural decision, I’d often find myself at loggerheads with my colleagues with none in the argument operating with any real evidence. And, invariably, to win I’d just test the hypothesis on a small scale, show the comparative data, and the decision would be much more clear.

Sometimes I was right, sometimes I was wrong. But the practice of testing intuition on reduced scope to gain confidence about a decision is one I use every day as an evangelist. And, as it turns out, it is a practice used by every person good at marketing. “It’s all a numbers game” people would tell me, leading me to believe that I’d be spending a lot of time in spreadsheets fiddling with a formula until it did what I wanted. Surely those charts and graphs meant nothing, and at the end of the day a small amount of math could be twisted to support my own preconceptions. “Developers don’t want a bunch of examples,“ I’d say. “Just give them really strong reference documentation, and they’ll figure it out.”

Not so. Marketing data shows in stark relief what works and what doesn’t and – especially when working on the Internet – is readily available if you spend a little effort trying to find it. Folks with a technical background excel at such, and wielding that power in this discipline can yield very powerful results, if less powerful buzzwords.

3) Calendar Management Is A Skill

Managing my meetings was by far the most difficult part of my first few months as a developer evangelist. When I was writing code, meetings were always something I could punt. When a reminder would come in and I didn’t feel like being bothered, I could always throw some headphones on, spit out a quick email about needing to stay heads down on a problem, and everyone would just magically wait until I was ready for them. People came to me.

Man, those were the days. A lot of marketing is gently aligning external forces to craft the right message and get it in front of the right people at the right time. And since those external forces don’t need me for a login page or a bug fix, they are far less inclined to tolerate last minute pushes or tardiness.

I must have run up and down Manhattan every day the first month I was at Twilio. I’d set a meeting at 42nd and Broadway next to one at Fulton and Church with 15 minutes in between. I’d double and triple book in email, leaving two or three of the parties asking where the hell I was. This function that had always been a nuisance in my life was now a critical skill and I found out I sucked at it.

Took a long while to learn. I’m still not very good at it.

4) You Can Learn To Schmooze

I’m not naturally very charismatic or talkative. Despite having played in a band and doing a fair number of technical presentations, it’s just not something I have a genetic talent for and I have to work very hard to do it. But in evangelism, this is part and parcel of the profession and indeed a valuable ability in the marketing game.

And, much to my delight, it is something you do get better at with practice. Programming is something I felt I could always just do. But public speaking, networking at a party, meeting people at a conference just never came as easily to me as writing code. It is now something I feel I can do and do well, and the only difference was a lot of practice.

There aren’t any real secrets. Ask people what they are working on, always treat them not as a means but an end, and be your authentic, flawed, fully present self. Nearly every human you meet will respond kindly. And those who don’t, you just don’t have to worry about.

It’s hard, but so is learning Erlang. And just like you cringe when you revisit the first Post-Nuke you ever built, so too will you when you recall your first attempts at building your interpersonal skills (just ask the kids at PennApps about my first Twilio demo. What a bomb on stilts that was).

Don’t get discouraged. Just grit your teeth, plow through and practice. You will get better.

5) The Impact You Can Make Is Huge

I long thought my maximum point of power to effect real change was in the text editor in front of me. The only way I could make an impact on people’s lives at scale was to write great software. While I still think we who can write code wield awesome power indeed, I’ve learned more parts of a startup than just engineering can make a huge impact.

While in the thick of the Olympics of hustling called SXSW, my paths crossed into a coder from LA named Will. He gave me a hifive for my Twilio shirt and said he was working on an app that would let people create disposable phone numbers to use for Craiglist posts, job interviews, and other calls you needed screened. My somewhat flippant question after hearing about his product was, “When you going to ship?”

“Soon, soon,” he said. “We’re working on it.”

“Well, hurry up!” I exclaimed. “People need this!“

A few months later he and his crew at AdHoc did ship that app, launched it on HackerNews, and the response has been incredible. So incredible in fact only a few days after launch, it helped a guy in Portland catch the thief who stole his bike.

After the launch, I got a very kind thank you from Will for the little push to get his app shipped. The right message at the right time to the right person helped encourage an intrepid team to finish a great idea, earn a lot of business and help a dude I’ll never meet got his bike back.

Now I can code all goddamn day and probably never achieve the same impact as that little conversation in the middle of a busy conference. Just a little encouragement at the right moment helped a team build something of which they are rightfully proud and serve some people who needed it. The satisfaction I got from watching that squad’s product blow up on the news was immense.

And when I’m doing this marketing thing right, that’s what it always feels like. I was anticipating a lot of different outcomes starting down this path, but I didn’t expect it to feel so rewarding. Good marketing is tough to do, good programming is tough to do – I’m starting to learn that anything good is tough to do.

And, for this hacker at least, doing something well will always feel magical.