I'm the CEO and Co-founder of Cobalt.io. I love startups and it takes a lot of courage to get going, so I applaud you for taking the leap and helping innovate in this space.
We started building the Cobalt.io platform back in 2013. We originally started as a bug bounty platform and since then evolved into a Pen Testing as a Service platform [PTaaS] over the last 5 years.
During this evolution I did a lot of thinking around crowdsourcing freelancers for security testing. I'll recommend these two blogs around how the market has evolved over the years and the different cases where bug bounties make sense vs. pen tests and vuln assessments. - https://blog.cobalt.io/deconstructing-and-rewiring-bug-bount... - https://blog.cobalt.io/the-third-wave-of-application-securit...
I believe you are in the bay area. Feel free to ping me at linkedin or twitter and I'll be happy to meetup.
Cheers Jacob