So I'm on a SMB team at my company and somehow stumbled across a massive opportunity and am trying to do everything I can to bring this puppy in. The buying signs are there and the sales cycle is going well. We have a somewhat commoditized SaaS product (job postings, TA resources, etc.) and are able to operate on monthly contracts (I only get comped on first month MRR anyways). It's looking like a decision will be made this month, as our sales cycles are pretty short.
Where my true worries lie is my managers ability to help me sell. I've only been at the company for 2 months, so my product knowledge is not super high, and am in need of support for things like demo'ing. This deal would be the largest, non-enterprise deal ever, but my manager and I are selling it with the resources of a SMB sales team, meaning that we really don't have relevant marketing material/ case studies to share. My manager lacks selling skills and I really don't even want to bring him into the conversation in fear of them somehow botching it. Do I dare attempt to go over his head to rope in one of my directors or VPs to help bring this in? Anyone have experience selling deals of this size and have any pieces of advice that come to mind?