As I type this out, I pretty much already know the answer, just double checking with the fine folks here.

Earlier this week I had a CEO from a bootstrapped startup reach out to me. She was looking for someone to help her company close deals. We chatted over the phone about the details, and supposedly they do software development in the mid-sized enterprise space, all deals are a minimum $1 million, deal cycles 6-8 months or more (for obvious reasons). They have no issue with lead generation and have plenty of opportunities, but they struggle converting (I wanted to dig more into this and will), and need someone with closing experience to help them out, they have some they are working with already, but need more.

The role would be commission-only, with the percentage to be negotiated once we agree to work together, and a base salary to come along later once I've "proven myself."

This was a preliminary intro call, and we have a follow up set for this week where I can probe further on a lot of the questions I have, but obviously I have concerns and doubts that this is worth pursuing further. Of course I'd love to make a hefty commission, but I'm not in a financial position where I can just go 6+ months without pay, and I don't know how sustainable it would be to work another job to meet expenses and work these deals. I know a lot of people work 2 full time jobs or 70+ hours a week, but it just seems like something will fall through the cracks. Also, this job would require travel to company sites (which they would pay for) which would mean I'd be taking time away from whatever job I was doing (even if a gig job like Uber). And then there's the worry that I'd land a deal but get cheated out of the commission.

So, I'm very much leaning towards thinking this is a dud. I know some people have mentioned meeting with CEOs or VPs at startups for interviews that ended up being more GTM strategy sessions that resulted in no actual job opportunity, but consults under the guise of interviewing. Not sure if that's the case here, but either way I'm not certain this is a good role at all for me. Also interested in hearing if anyone else has had CEOs reach out to them for these kinds of "opportunities."

The job market.... is it true?

Bootstrapped startup commission-only role, bad idea, right?

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