What qualities do you look for when hiring for an executive operations position?

This depends upon where you are in the start-up continuum. If you are still in search of a viable business model (i.e. the start-up phase) then the "multiple hats" scenario is spot on. In this phase the key is to discover that which is repeatable and scalable. In other words - to put your energy and resources into discovering things like: -Who your market is -What your positioning is -What your offers are -What your pricing model is -Where your market is (aka what channels to use for inbound and outbound marketing) -etc Warning: It would be a mistake to think you already have these things figured out when you haven't. In my experience - mastery of these "basics" are what separates successful businesses from floundering ones. And no offense - but if you are only at $1.1M in gross revenues then it seems to me like you are just beginning to figure these things out. Due to the need for flexibility in this phase (some call this being "agile") you are best served by a team that is willing and able to do what's needed. There will likely not (yet) be any "established" positions. And with (gross?) revenues of only $1.1M it would seem that you wouldn't require a large team anyway. [I suppose this depends upon your current business model - so I apologize for making this assumption.] Once you've discovered a viable business model - then it's time to build systems (since you will only then know all that goes into making the sale). These systems will help you efficiently and effectively scale and repeat. It's at that time you would start creating "positions" (aka jobs) and hiring staff to do what you discovered works. All in all - Much depends on where you are right now in order for me (or anyone else) to provide you with more specific direction. I'd love to talk this through with you if you are still looking for assistance. Best of luck!

"What was the best part of you day?" Ideally you could ask in the afternoon .. but it sets a positive intention. I ask this to all my friends + wife everyday when I see them.

It's great that this employee has been transparent about the fact another company wants him. The problem is that this employee is ambivalent about his connection to your Company. Really, under 100 employees at least, this is unacceptable. I would first reflect on why you think he's looking elsewhere. Then, I'd ask him that, admitting that you have failed to create an environment in which he has stayed engaged and motivated on what he's working on. If his answers seem reasonable and you can commit to making the changes necessary, then you won't need an employment contract, he'll stay on his own desire, because you listened to him and improved his situation. If his requests seem unreasonable or you know you won't be able to make those changes, fire him *today.* This situation can contaminate your entire company quickly. Yes, swapping someone out will always be a bit of a setback, but you want *everyone* on your team, feeling motivated and excited by what they're doing. It sounds like you're making your decision out of fear (having to find and hire another engineer) versus what's best for the Company, long term. Happy to talk to you in a call. Problems like this are within the sweet spot of my skills and passion.

Please resist the urge to pull the band-aid. I'm not a fan of keeping a poor performer, but unless this person is a behavioral or "for cause" termination, he deserves some professionalism here. 30-day Performance Plan, make the goals aggressive and stick to it - he can consider that his head start to either buck up or start searching. Remember, your other employees watch how you treat their former colleagues. A quick termination before a holiday is prickish, an aggressive performance plan is taking care of business.

I think you should first really step back and ask if you need that role filled. Are your sales growing? Are they growing as quickly as you'd like? Do you think someone could push that needle? I've worked at companies with strong focus on sales and some where there were no sales people at all. It depends on your niche and who your customers are. Depending on your outreach methods, perhaps you need to hire someone with a strong sales background who's going to pick up the phone and start cold calls all day, or maybe you just need someone to handle your marketing better and help you out with some Adwords campaigns. Business Development is a big term, and it can cover a lot of things, most commonly sales... but salespeople aren't right for every business. So, look at your existing success. What sorts of things bring in the money now... and look to amplify those existing efforts before you go breaking new ground. You should be looking for someone who complements your existing success and can continue to tell that story, in your existing playing fields, and gradually moving into new areas. I know this was a vague answer, but I hope it helps.