Role playing

You'd think that it is pretty simple to staff an early stage startup (of the software kind) at launch. A CTO/Architect/VPE, a VP of Marketing and a VP of Biz Dev/Sales (though this function could wait until the product is close to being ready), a few engineers to build the product, and a CEO to pull it all together (other functions like hr/finance could be contracted out until later) - that should about do it.

But the script isn't always so simple. What needs to get done and the roles to be played at the very early stage depend on the product/service/delivery and how well-defined it is. Sometimes the venture is built around building a better mousetrap, in which case the roles/responsibilities are clearer. But if you're framing something new, it will most certainly morph based on market, technology, investors (yes, it happens) and of course the team itself, so who you bring to the team and the role they would play is important. It also depends a lot on who the customer will be - selling to an IT manager in a mid-sized corporation will need a different mindset than selling to pre-teen girls (and the person who's credible talking to one may not have cred with the other).

The other factor is how well you know the capabilities of the people you bring on board. Resumes don't tell you the whole story, and are often helpful only when you're looking at a 'standard role' like that of VP of Engineering. If you're aiming for someone who can be hands-on and manage the development, there are a whole bunch of people out there. If you also expect them to so some design, the number shrinks considerably, and if they should be able to talk sensibly to customer groups and contribute to product direction (because, at this stage you'd better have design, development and customer research all working closely together) - your available pool just got to bathtub size, and if you factor in the requirement about joining at the very early stage and working for equity, you've just skinnied it down to a bird-bath. So you have to figure out a way to (1) find this small set of available people and (2) suss out which of them could take on the role of a generalist while boasting a proven track record as a specialist.

And lastly, once you figure out the right person, you have to play the all important name game - what's the title of the role(s) to be played. It has to be both attractive as well as appropriate. Practically everyone thinks they have to be a 'C' something or the other if they join a startup, but does their experience really warrant it? And should the person doing the design based on user-feedback be in 'product marketing' or in 'architecture' as they'll be doing both? Possibly whichever one they hope to do long term, as long as they're aware they have to do both at the beginning (I'm partial to 'product design' myself). And frankly, it would be a great to have a relatively flat organization and avoid all the hassles of which function reports where - though that works only with the right team.

The important thing is that this is not just about the founder/entrepreneur's challenge in building the team, it is about the challenges that each individual team member has to take on. If you're expecting your marketing person to handle all aspects of marketing, advertising as well as sales, biz dev and managing product definition, s/he should know what's expected and should want to get on this ride. If the startup's an ensemble group, it helps enormously to have willing actors who at least know what their roles are about and what the cues are going to be before the enter the stage - and yes, it's an improv, with the ensemble making up the script as they go along.