A few things: Startup founders need to be convinced that you'll be willing to do the work that at big companies you might have had a support team for. So you need to prove that nothing is beneath you. The best way to get their attention is to demonstrate the type of work you'd do for them right in your cover letter/email. (ex) In your case it could be sending a recording of how you might lead a technical demonstration for their product even if it's just a mock demo.

Also, I'm not sure how early stage you're willing to go (looks like you want at least 10-20 employees), but with your experience you can fairly easily start to engage startup founders that are just starting to think about building out a sales team and process, and help guide them. Whether it's tips on how to create pitch documents, how to set meetings, or the best way to think about how they will scale their sales team. I've seen a number of startups where someone has started off as an advisor (whether formal or informal) and later on was hired as a FT employee. This approach might take some time, but at the very least you'll build relationships with interesting companies and get to see how they're run before joining them.

I can't speak for all startups, but I have worked for a couple, and this is what I know:

- It's very easy to be overqualified for a startup. We are looking for brilliant people we don't have to "untrain".

- Price is also a big factor. We can't afford to bring on experienced salespeople, who will often require a certain level of pay and benefits for their experience (we're not even set up to offer benefits yet). What we really offer is future potential for growth and personal investment.

- Startups really value loyalty. It's great that you are up to speed on coding and have side projects, but you don't want to convey the message that you aren't devoted to your day job.

- Have you applied to a wide variety of startups, or just the big "cool" ones in your area?

Is there any reason why you want to work at a startup? Unless you're a founder, working at one can be a frustrating and unrewarding experience. The vast majority of workers are fresh out of college and trying to build experience; either that or super-stars brought in to give direction.

Thank you very much for your feedback and insight.

Comp has never been an issue, but I usually don't get that far. I definitely do have some base requirements in terms of what stage the startup is in from a maturity/funding standpoint, because things like benefits are a deal breaker for me. My comp/equity expectations are definitely adjusted for the fact that I am not a founder nor likely employee 1-5 or 10, and if numbers are ever discussed, we're always in the ballpark.

Your first point about being overqualified is a good one; I don't know how I can demonstrate that I'm not expecting a 'process' or an 'environment' in which to sell; those are both horrible at my current company, so I wouldn't want them if even given the option.

I don't know how I square your circle of staying relevant in terms of technology unless it's my day job; that's what I'm trying to do! I'd love to get my 'geek fix' at work and not after hours.

Maybe your cover letter is a bit too straight-jacketed. Some candidates I have looked at try too hard to convey professionalism, when what we want as a salesperson is personality.

And about the app: one of the red flags for us is someone's side project. The nature of a small startup is that everyone has to live and breath the work (we all have terrible, terrible work-life balance). Some projects are fine, but for our salespeople, we don't want them selling anything else on the side. You can't serve two masters.

Other than that, I don't exactly know what I can offer. Being in Seattle, I imagine the hiring scene is completely different down there.

I'm curious, have you been burnt before by sales people with a side project? My intuition is that if the products aren't competing there wouldn't be a problem. Do you have anecdotal evidence to the contrary?

I would recommend rewriting your CV to focus on the team, department, project, etc you were part of rather than the company. Most companies operate like a conglomeration of smaller companies, so make the most of that. I would actually leave off the big name and use something that sounds smaller - instead of "BT" try "BT North America".

I'm looking for help with Sales in my startup which provides IT training. It's a very small company. I don't describe it as a "start-up" because it's been around 5 years. I'm doing it full-time now (4 months already) so it's definitely coming along.