As the Interactive Art Director here at Dumbwaiter, I communicate with clients on a regular basis and I am largely responsible for making "the pitch" that gets us new work. It's a 98mph strike-3 fastball down the middle of the plate, in case you were wondering. What I've found through personal experience is that CEO's, Owners, Founders, Presidents, and Vice Presidents shouldn't cause us to panic when making these pitches.
These are the people who ultimately have to deal with the success or failure of the project (and they usually write you a check), so it would make sense to be scared of them, or at least a little intimidated, when trying to convince them, or the people that report to them, to hire your firm to handle their web needs.
However, these are typically the most down-to-earth, logical, intelligent, direct, and honest people I have ever had the pleasure of working with. People I can communicate with effectively. People whose trust I can gain through concise, intelligent conversation. These are the people I can most comfortably have a beer with. These are people I get excited to meet whenever I have the chance.
I've become friends with many of them:
Tim Barber: Executive Creative Director of Nurun (Formerly Odopod)
Brian Chan: Founder and Chief Software Architect of Liferay, Inc
Gary Domenico: President and CEO of General Code
Therese Hannigan: President, Founder, and Creative Director of Dumbwaiter (Yup, that's us.)
They understand success as well as failure and handle both objectively. From the top of the company ladder, they can see the bigger picture. However, they rarely have the time to be directly involved in the project so they put their trust in a team to be the leaders of that project instead. Their desire is and should be, to ensure that the right people are set in place to make the project a success.
The truth is that the only way you can scare me away from your web project is by putting the wrong people in place to work on it. The human resources team, the marketing division, technical staff, and even your maintenance personnel don't scare me. But if the those aren't the right people to be working on your project, I quickly become terrified.
What scares me is bad communication.
Web projects usually fail and succeed for the same reason: communication. Website redesigns and overhauls usually do not fail because you hired a company of people with sub-par skill sets. The quality may vary, but they won't fail. These projects usually fail because of communication breakdowns. When they succeed (high quality, on-time, and on a budget), it's most often a result of excellent communication combined with the design and technical expertise of the firm you hired.
The right person to be in charge of your web project is:
Poor communication is my greatest fear when starting a new project. Choosing the right people to be in charge of your web endeavors is the most important step to setting yourself up for a successful and enjoyable experience.