Why I joined FreshBooks

Feeling wonderfully refreshed right now, after a week lounging on a beach at the West end of Jamaica, followed by a week back in the country reconnecting with the kids and packing in a little skiing in this gorgeous Spring-like weather.

Beyond the vacation and family time, though, there's something else putting a major bounce in my step these days, and that's the new gig.

I've been kind of coy about where I was going to land after Thornley Fallis, for a couple of reasons, but now it’s time to come out of stealth mode and ‘fess up to the fact that I’ve jumped enthusiastically into a brand new role at FreshBooks.

It's always exciting to start a brand new job. Getting to know the new people, figuring out which end is up, starting to piece together the clues that will eventually drop through the filter and end up as part of the big plan for the year ahead. I've always loved this feeling of starting something new. It's just invigorating.

Coming to FreshBooks, though, is like taking this feeling and cranking it up to 11. Everything about this opportunity just felt right, from the very first moment Mike McDerment and I started chatting about it. After ten years in the agency world, I already knew my next move was likely to be back into the software business; back to the roots and backbone of my career. So when Mike pinged me a while back to ask: "Ever thought about coming client side?" my immediate gut reaction was "Hell yes!"

This is no exaggeration: if I'd sat down and made a dream list of all the software companies in the world I might possibly be interested in working with, FreshBooks would have been right at the top.

Why? A whole slew of reasons, I guess, but let me see if I can distill some of them into the main categories:

1. The people

Ask just about anyone in the Toronto (or broader) tech community what they think of FreshBooks and you'll hear something like "Oh - those guys are great!" The reputation of the team here is as well-deserved as it is well-protected.

They (we!) have some of the best people you could possibly hire if you wanted to build a kick-ass software team - seriously. The people I'm working with are just exceptional. Plus the integrity and culture is fiercely protected by one of the most intense and in-depth hiring processes I've ever come across. You don't get to join the FreshBooks team unless you're a clear and strong fit. They've got a really good thing going on here and they're smart stewards of the team balance. Getting picked to join FreshBooks is a little like winning software Olympic gold.

I guess I'd been in a kind of complementary orbit with the FreshBooks folks for a few years now. I got to know co-founder Mike through his role with the mesh conference and meetings at various geek community events. Long before we ever talked about working together, I'd also voted for FreshBooks twice as a judge of the PICK 20 Awards. I did so as an honest admirer of the way they do things here and the role many FreshBookers play in the community. Along the way, I got to know Corey Reid through our involvement in HoHoTO, and several other team members through other channels. I liked everything I saw about the FreshBooks team - people who were way smarter than me and would drive me to create great work.

In short, it just made sense from a personal fit perspective.

2. The platform

The core of what FreshBooks offers, as a web app, is deceptively simple. We're in the business of getting people paid for what they do.

If you're a freelancer, a small business person, an entrepreneur - that's a pretty compelling statement: we get you paid. I like the idea of a business being built on such an elegant economy of purpose.

Yet it is, as I said, deceptively simple - and remarkably powerful. If you can absolutely nail one of the most basic needs of any business (raise an invoice; collect money), just think of where you might be able to go beyond that...

Obviously, I'm not going to start getting into any roadmap futures here, but while the current FreshBooks product itself is pretty darn cool, there's also a long, long way you can go when you're starting from such a solid main idea.

I've often said that the thing I missed most about working in consulting roles in the past 10 years was the enforced distance from the product. When you're a consultant, you get to advise and, at best, influence - but you rarely get to really own the thing.

Getting back into a software company is a lot about getting back in touch with my product marketing gene. And here, it's not just the product; it's the platform and where we can go with it. Thinking about that has instantly kicked my creative mojo back into high gear.

3. The promise

Another key factor for me in weighing the decision to join this team was the overall promise of FreshBooks.

Note: I'm not talking about the "potential" of the company or what this might translate into in terms of stock options and other material aspects (although that stuff is appealing, of course).

Potential is something that might be achieved, if the stars align, you execute well, and the conditions are right. Too many variables there.

A promise, on the other hand (for a good Catholic boy like me), is something you're brought up to deliver on - and the FreshBooks team has a strong record of delivering.

But it's more complex than that. On reflection, "promise" may not be quite the right word for the solid feeling of confidence I have about joining FreshBooks. It's a very young team, and yet there's a certain quiet maturity about the way these guys conduct themselves.

From everything I learned prior to joining, and everything I've been able to glean in my very short time here, FreshBooks feels like the archetype of a new wave of post-Cluetrain businesses. These guys are, IMHO, one of a relatively small group of companies built from the ground up around what you might call social business principals. Or, at least, you might call it that if you were in the business of applying wanky labels to doing the right thing.

Think about Rackspace, Zappos, or FTJCO - these guys are among a handful of companies who've emerged in the past few years doing things in a completely different way from what customers in their respective markets had grown used to. It’s not necessarily a revolution – that part already kinda happened when the read/write web emerged. It’s more that all of these companies, FreshBooks included, take a certain engaged cluefulness as read amongst their teams, customers and suppliers. It's in our DNA.

We can’t dissemble, couldn’t fake it if we tried – we’re just naturally inclined to run our businesses the way things should be done because we're simply not wired to even contemplate any other way of doing it.

It's not about social media, but one example of what I mean can be seen in the way these guys have applied the principles and tools of that space. Look: there are thousands of companies out there doing cool and groovy things in the social media/Web 2.0 universe. That's all good. But what I've always really liked about the way things work at FreshBooks is that social media (indeed, all forms of media) are just standard, accepted parts of the job, they're not the job itself. Nobody here puts out a blog post because they think you gotta have a blog. They blog, email, snail mail, tweet or even just pick up the damn phone on the first ring because that's part of the job.

In a world where every customer is engaged and every customer has a voice, the social media tools and principles are hardly worth even thinking about any more - they're just all part of the new perspective included as standard in our view of the world. It’s the business that’s the thing, not the tools that help us run the business and service our customers. Yes, there's a certain essential philosophy of transparency, authenticity, and immediacy often associated with companies doing things in the social media world - but it's the attitude that's important, not the technologies.

tl;dr - I've been doing this stuff for long enough now that I like to think that I get it. And I also think I'm a good judge of companies that get it. These guys got it a long time ago.

4. The position

So what is it I'm actually going to be doing here? This is one of the best things about the new gig. My official role is Vice President, Marketing Communications. A fairly ordinary title, perhaps, but here's why I think that's so cool...

Way back before I went over to the Dark Side of PR agency life, I spent many years running just about every aspect of software company marketing you can think of. As a Jack-of-all-trades and all-round marketer it took me a while to figure out the aspects of marketing I was most interested in (and best at).

One of the main reasons I moved into PR was that I'd finally discovered communications was the slice of marketing I loved the most. I figured going into the agency world was a good way to focus on that specific area and get better at it - and I learned a hell of a lot in those 10 years.

So while I'm still fascinated by every facet of the marketing puzzle, I know enough to realise that I'm far from an expert in all areas, and the world of marketing has moved on a long way in the past few years.

The great thing about this FreshBooks gig is that they already have a terrific VP Marketing who is really strong in all the areas I'm not (and vice versa). Mitch Solway is marketing yin to my communications yang. Minimal overlap, maximum fit. It rocks.

So my gig is part storyteller, part flack, part marketer, part evangelist, part author, part creative director: it's a job that is broad and diverse in scope and, in some ways, needs to be defined through doing it, as we're creating the role from the ground up. There's a huge amount to do, a ton of remarkable stories to tell, and an even bigger story still being written through every customer interaction, every single day.

In short, as you can tell, I'm pretty excited about joining the FreshBooks team. This feels a lot like coming home.

My first official outing as an ambassador for FreshBooks will be at the SXSWi festival kicking off in Austin, Texas later this week. Come find me if you're there and you could win one of my shiny new business cards.

Got to go now, the support lines are calling...