Oh this is a long question to answer, but let me start with my experience. I'm the "outsourced COO" for a number of small businesses who have grown through their bootstrapping phase, proven they have a market and all of sudden start feeling the pressure of the business expanding. 9 times out of 10 what they need is someone to wrap their arms around all of the operational stuff, mature their processes, put systems in place, connect their data, introduce greater discipline in the production of their core offering, make sure they have the right service providers in place (lawyers, accountants, bookkeepers, etc.) and they can easily and quickly get access to the right metrics to understand how the moves they make affect their desired outcomes. This is an important and often ignored role and is the key to relieving a hard-working CEO of the things they likely don't do "well", and allow them to focus on building their business, usually on business development and strategy. I think it is smart for you to consider adding this to your roster, particularly if your time is better spent on more strategic work.

More and more I would say that sourcing this kind of talent from recruiters and executive head hunters is becoming ineffective. You are best to scour LinkedIn and use your personal network for recommendations. You are far more likely to find good people this route than relying on the "you get three options" approach that many agencies will offer. You know your business best and who is going to fit.

It sounds like you are still relatively early stages. Don't worry about titles. The right person will be someone who has been there before, in a growth phase of a company, and knows that titles mean nothing, other than to better define their scope of work and help the employees understand their role. If you find the right person, they will be able to tell you exactly what you need from an operational perspective. I fear if you try to turn this into a CEO role, you will find someone who doesn't want to get mired in the details and focuses on the strategic work (appropriately), so you will end up with the same problem. Go find someone who focuses on, and is excited by building the operational foundation for your company. Someone who is going to say "OK, go build your business. I will make sure everything works to support that." They should also know how to scale operations to meet projected demand so you can work as a well-oiled machine.

Additionally, look for someone who has run a company before. I certainly earned my stripes when I went through this myself. Your candidate should understand business process engineering, change management, resource management, service design, financial and data management, systems and technology, etc,

Don't skimp on compensation. Pay them what they are worth and make the offer attractive. You will lose senior resources in a heartbeat if they don't believe you value their skills and are ready to make them an integrated part of the team, and to trust in their experience. Senior resources are not motivated by money but by the challenge, the team, the knowledge that they can be successful.

I hope this helps. Happy to chat further if you have some more specific questions.

I have a completely different take on this. Before that, a bit of a background about me. I am the cofounder of one of the leading fashion ecommerce companies. I started and have scaled the venture to over 150 employees with multi-million dollar revenues. Before this, I worked with a large company for over 10 years.
Before you think about taking your hands off of internally running a tight organization and bringing someone to do it(be it a COO or a CEO or a MD, you should really think of implementing a very strong performance management framework. I have learnt this the hard way when I had to scale from 25 people to over 100 people in under a couple of months. Culture, performance and goals went haywire.

Give it a thought, your 31st employee that you hire will not have the same passion as you. For him its just about being in a job and taking home a secure salary.

You need to build a robust framework for performance monitoring in real time which also accommodates a way to keep people motivated and aligned with your goals. You also need to have some kind of a structure where compensation is linked to performance.

I implemented OKR in our organization. This is what is used in Google, LInkedin, Intel ect. Its very strong and robust. I tweaked it a lot to make a solid framework that is also very simple.

Once you have this in place, you could look at hiring a COO and you can start focusing outside for either bringing in investments or looking after distribution and alliances.
Your COO and your framework will ensure that the organization is aligned with your and your board's goals. and will be able to deliver results and at the same time, you will have a performance oriented culture in the company.

Hope I have been able to articulate my thoughts clearly. Please feel free to revert to me if you need any inputs on this. I would be happy to help you in actually implementing and monitoring this.

Regards
Vivek

First of all, don't get hung up on titles. Do what you are really best at. Are you best a marketing or management? Hire a CMO, chief marketing officer to fill both roles or take the position yourself until you grow to the point of needing more "chiefs."

However, make sure you have a person who has a strong passion for marketing in that position. No sales = No money.

Best of Luck,
Mike
From the Trenches to the Towers Marketing
I will be glad to help as my time permits.