Viral Marketing expert. Pioneered Social Gaming industry (Vampires/Zombies) with 50M+ users. Created 1st version of @Causes. Founder @BuildForge (Sold to IBM), Founder @Ohai. http://www.blakecommagere.com
I built and sold an enterprise company to IBM. While the fundraising climate was very different then, here are the things you should look out for:
As a general rule, if you're going to raise money, then you want to raise enough money that you can get the company to the next stage at which you'll be able to raise another round. Were I in your position, I would raise enough that I could confidently establish our LTV, churn, CAC. Once your LTV is at least 3x your CAC, you've built a business that many investors would readily fund.
A few tips:
1) You will _always_ need more money than you estimate. It is better to raise 30-50% more than your initial calculations of what you "need" - if you raise more than you need, you took a bit more dilution than necessary. If you raise less, the company will likely fail.
2) The CEO will likely be the best salesperson at this stage and for a time to come. Don't hire more than 2 additional salespeople until you are certain you have a scalable, repeatable playbook.
3) If you haven't read the sales learning curve - it's a quick intro to scaling a sales org. Running sales is very different than running eng. Very. https://hbr.org/2006/07/the-sales-learning-curve
Happy to share more about my experience if you'd like to do a call. Good luck!