Ask HN: How can I get your attention?

Hello HN. I've been in presales for almost 20 years, the last 15 in management selling software solutions to enterprise for a fortune 50 company. I'm incredibly well compensated but feel I've plateaued in terms of career growth due to limited movement in our senior management ranks. More importantly, I am really not interested anymore in the software we sell. During demos of our 'latest' product I sometimes have to pinch myself to keep awake. Long story, but short(ish) set up to question: I'm really interested in small disruptive software companies. Especially those that are in B2C rather than the B2B, the companies with those ideas that make you say 'wow', why didn't I think of that? The problem (I think) I am having is garnering attention from such companies due to my long tenner in somewhat unrelated software fields. I've sent resumes and typically I hear nothing, or I am outright turned down. So, after all that, here is the question: Has being in enterprise software for a large company for so long tainted me, and what can I do differently to draw the attention of the companies I am interested in?

What do you want to do at the small disruptive B2C software company? Are you wanting a technical development position? Product Management? Operations management? Partnership development?

It occurs to me that being "incredibly well compensated" at your current position could be both at the heart of the problem as well as holding the solution.

Problem: If you are already making 2X or 3X of what the small disruptive company is paying anyone in the company today it is really hard for a founder to figure out where to slot you in, and to believe that you will stick around and stay motivated for 1/3 your current salary.

Solution: If your compensation has been well managed then you should be in a position to invest several hundred thousand dollars. And that, combined with your sales and management experience might be really attractive to a technically sophisticated founder who needs a co-founder with business experience.

It seems to me that you want to be involved in startups that have just got traction in the B2C market, AkA created that 'wow' factor that you mentioned.

Your long track record in a fortune 50 company might be the thing that steers you away from getting accepted to such companies. If I was hiring you, the first red flag I'd get is 'this guys experienced' - how much is this going to cost me?

Likely, the jobs at small disruptive companies probably work on recommendations. I see your options like this if you want to make the change:

Option 1: Get a recommendation to a company your interested in and expect a pay cut.

Option 2: Find a startup that you're interested in, offer to help them out, make connections; or, join one.

Option 3: Start your own B2C startup, do it as a side project, build a team and quit your day job when you're ready.

There is nothing worse than doing a job that you're no longer interested in. I know your pain, everybody has been in your shoes at one stage in their life.

This is my email, your welcome to email if you want any advice, lukejamesfitzpatrick@gmail.com

I'm realizing given my experience, operations management is probably the area where I would contribute most, at least early on. As an organization matures, sales strategy and execution are areas where I'd ultimately offer value. As I mentioned in another reply, I help co-launch a (failed) startup prior to moving into enterprise. The experience for me was really the school of Fort Knox in the sense that it wasn't just one role but was many (sometimes all at the same time).

I agree with your description of the problem. It's your solution I'd have trouble with - money is invested in secure but low yeild areas - the wife is extremely risk adverse. She's supportive of my aspirations as long as they don't touch the nest. Although it's something I'll need to consider. Thanks so much.

Definitely promote the value you can offer. In some ways coming from a large business is a plus- it gives you different insights that a bunch of 20 something founders may not have. You know what works really well and what doesn't in terms of operations, have experience with different types of sales channels, can help the company grow, etc. Too bad you aren't interested in B2B startups. ;)