Sorry about just getting back to this, I didn't think there'd be such an interest. I'll go in order.

1. >> I mean, you're in NYC. Are you referring to someone outside that area?

Yes I'm in NY (Westchester, actually). I'm thinking of people in NYC and San Francisco, so no, I suppose it doesn't answer your criteria of being outside those two areas. That said, I also know someone who makes this much and works remotely for a company in San Francisco, so he gets the best of both worlds.

2. >> How would you go from an entry-level infosec position to $250/yr?

For someone who decided to make a career of infosec and make that sort of salary (or the associated industry prestige/research you generally end up with at that level), it would take 6-10 years of exceptional work, original research and tool development. If you don't want to do all three, pick two, but you better make those two amazing.

Let me break down rough salary bands for you (keep in mind these will change based on a specific firm):

a. Associate - This is a bottom rung appsec engineer. If you join Matasano or a similar firm with promising intuitions about security and a background in development, you'll end up here. Great! $70-90k salary (there are outliers above this, and you'll see salaries for 50k - 60k, but if you know what you're doing with job searches and it's a good firm, that's the range). You usually stay here for a few years, training under the wing of mentors, until you competent in at least 3 different disciplines of information security (crypto, mobile, web app, network, incident response, reversing, malware analysis etc. etc. etc. and there are overlaps). You'll also stay here until you are ready to supervise someone else running a penetration test and can handle clients on your own.

70k - 90k

b. Consultant - You should be competent in 3 to 5 different disciplines of information security (or ridiculously stellar and potentially famous-in-the-future in 1-2). At this point, you probably haven't presented at a conference yet (and many go their entire careers without doing this), or done original technical research, but you're probably developing security tools or thinking about it. Any good firm is going to give a performance bonus for this. It's most likely taken you 1 - 2 years to reach this level, depending on innate talent, motivation and practice.

90k - 130k

c. Senior - Similar growth progression, now you have 5-7 disciplines under your belt, expert in 1-2. You're either doing original technical research or considering it, and you develop new tools are part of your research. You might present your research at conferences, you might not (most people who do meaningful research tend to submit). You now lead teams and projects for large engagements with "important clients" in the consultancy. Probably took you another 1 - 2 years to reach this, maybe 3.

130k - 180k

d. Principal - You're probably known in circles that know your consultancy, because you're one of the most important consultants at your firm now. You might even be industry-famous, if you have done particularly good research or released a tool that made pen testing easier for everyone. You're expert in 3-4 areas and it's no longer worthwhile counting how many disciplines you could technically operate in because the overlap is superfluous. It's likely taken you 1 - 2 years to reach this from Senior, if you are motivated and keep working.

180k - 250k

A few notes:

1. None of the definitions here are "hard" - don't take how many disciplines and similar such criteria as hard rules, it's just a rule of thumb.

2. These salaries are before bonuses such as for extra travel in a quarter, extra work in a quarter, tool development, research or conference presentation (you bonus for all those).

3. You'll notice salary ranges increase as you go up, because the higher you go the more nuanced the skill levels become.

4. There is a level or two above principal, generally "partner", "distinguished consultant/engineer" or something similar. You're basically at the top of your career as a consultant here and can found and manage consultancy firms. The salary here is $250k+.

5. You can skip, and the years are basic averages at best.