What title should I use and should I require D&O?

I have been a startup advisor for a colleague of mine for several years. He is primed to go from incubatory stage to launch and has some excellent blue-chip customers lined up. He is having admitted issues closing his first big deals and has asked me to assist him. I am willing to give of what time I can (uncompensated) to help him close his first few deals and generate some incoming revenue.

I will be representing his organization in some upcoming meetings. His initial thought was to title me COO and provide business cards for legitimacy in business meetings. I see a number of issues with this as I am an advisor and not an an officer of the organization much less an employee. This could also be a flag if he goes for funding in the future. What title best provides the proper legitimacy for meetings without raising flags? My initial thoughts were Advisor, Strategy Advisor or possibly CSO.

My interest is for my colleagues' success. I want to help him launch. I also want to know, however, if I am opening myself up to liabilities in my assisting him. Should I require D&O insurance for this pro-bono assistance?

Personally I would use a card with no title on it. This is done far more than you would think by people at the highest levels.

The key is to have an extremely high quality and simple card, you will be immediately perceived as important.

If asked what your role is or why you are at the meeting you can simply state that you are there to facilitate a deal.

As far as liabilities, don't sign or promise anything. Seriously though, the cost of insurance may be excessive for his company. This is your call, and everyone has their own risk tolerance level, but if you generally trust him and know his business then you are probably fine without it.

In these meetings I assume you will not be representing yourself as the final decision maker for his company? You are not going to sign contracts or use sentences like "It's a deal then." are you? Rather you will be saying things like "This looks like it will be acceptable but I need to refer it to my colleague who will be making the final decision."

There is no golden rule saying that you have to have a title on a business card, but what is stopping people from asking you what your role is at the company? Not having a title on your card is one thing (and is fine as JonnyBoats points out), but what happens when you're asked of your role, what do you introduce yourself as?

I would definitely role with the title of Advisor. Considering a lot of people in Advisor roles are independent from the company itself, I'd say you've been hired as an Advisor or Financial Strategist. So your title would most likely be Independent Advisor or Independent Financial Strategist.

Advisors don't usually represent companies, and don't have fiduciary duties that require D&O insurance (your only duty is to act in the interest of the company and disclaim any conflict).

If I were you, I would ask for a special power of attorney limited in scope, with an addendum signed by both of you where you cover the liability problem. After you have the power of attorney and you can represent the company, the title is a formality. Anybody with a legal background can draft this agreement, it's nothing complicated.