We're looking to hire a seasoned COO. What package would you pay? cash/ equity mix probably flexible (our run-rate is c$3.5m pa).

Nothing. Business transactions should be spoken about in the plainest possible way. People using terms like this come across as lacking credibility (at least to me). Besides, a deal is never crafted, it is always negotiated. Crafting evokes a singular emphasis whereas a deal always involves two parties. I would avoid using this term and avoid anyone who describes themselves as having this ability

You have to be careful on selecting your co-founder. I know it's an already cliché to mention it, but selecting one is like selecting a spouse to marry. You need to know the person first, and even some investors and accelerators dismiss automatically startups because the founders didn't meet before working together in the startup. If you're doing a tech startup, the co-founder should have a technical background if you don't have it. That will save you a lot of money when you're bootstrapping as well as making sure you deploy a great product as soon as possible. Once you want to work with someone, my best advice is to hire them to do a project or a task inside the startup. More than words, you need to see them in action and that way you can evaluate your chemistry as a team. When you already worked the details and decided to create a startup together, you need to be smart about the plans. You need to sign a partnership agreement and put the equity in a vesting option. In Silicon Valley, the standard vesting period is 4 years with a one year cliff. After one year, the founders fully own of the 25% of their shares. That means if they leave the company before the first year, they will not have equity in the company. Having all that in mind, I think it will help you select the best co-founder possible and also be a better bet to investors if you ever decide to raise money. I hope it helps!

Ask them! If you don't have any similar interviews yet, get some done in a niche close to this one. Credibility is important, and if you show you've done some and they listen to just part of one interview, that can be what pushes them over the edge. Everyone likes to talk about themselves. So don't be afraid to make the connection. I work with a local pro soccer team and it was easy to connect with a senior management team member. From there, the players are all accessible. They're just regular guys, running around and wanting to have a good time. You could find the marketing director and ask who's the best talker of the bunch. Be sure to let them know they get to use the content as well. The teams are looking for reasons to be in the news. You're giving them one. Something they can share on their Facebook page, or in an email to their fans, that helps their followers feel closer to the team, is valuable. Don't get stuck thinking you're trying to "get" something from them. You're giving something, too.

I'd take a look at the large, established companies in the technology space in which you want to operate. Somewhere at one of those companies is an astute, experienced person who might be ready to get out of the big company environment if you come along with the right idea. E.g. Cisco if you are doing networking, Salesforce if you are doing marketing automation, Intuit if you are doing financial apps. The trick is finding one who not only has the technical expertise and wants to get out, but is well suited financially and psychologically for a startup. I learned the hard way that co-founders who are not in the same boat financially can make for an unhappy parting.

If you're looking for Ruby folks, go where they go - local meetups. Second would be online but you will need to mine Stackoverflow, Github and similar sites and realize that they get approached regularly so start engaging early (at least 3 months before projected start date.)