I see too many startups that have Management Team pages that run a mile long on their web sites. Well-funded startups usually make the mistake of hiring too many executives at the wrong time. Executive hiring has to be done very carefully, according to where the company resides in its lifecycle.
Also, executive hiring involves not only evaluating the individual but also the organization within the company. If you're looking to hire a marketing VP, are you sure that the marketing organization needs to be fully built or expanded? Or, are you really looking to hire a director or manager (or two) who can pretty much carry the day-to-day duties that are required to support the field, put up a cool web site, run some lead campaigns, and so on? I realize that this is a simplistic view of the world but the difference between an executive and manager look like this ... the manager knows what you could or can do, the executive knows what you should and must do. The manager has confidence in implementing. The executive has confidence in deciding. The manager knows how to spend dollars. The executive knows how to direct dollars.
Said differently, do not hire a marketing executive with nothing to do and no resources from which to create output. Organizational output is pretty much what you'll assess the marketing executive on and, thus, you need to evaluate this realistically. If, on the other hand, your startup is on the "brink of XXX" and marketing is a critical endeavor, find a marketing VP and empower him.
Here's what to look for in a marketing VP if you're a startup and you really must hire one ...
* Get someone who is hungry and out to prove something. This is critical. This is why companies who hire the same set of VPs who have been playing musical chairs end up tossing them after a year or so. About three months pass and it becomes clear that your hire has no clue about what marketing means. You realize that a bureaucrat has just joined. The marketing VP starts to budget and hire a bunch of the same cast of characters (suppliers and outside agencies and consultants) to basically do all the work. You've just been fooled. You purchased a turnkey marketing virtual team. Any marketing VP who has been around doing the same thing for 10 years or more will know nothing about current market dynamics, marketing techniques, marketing tools, talent pool to tap into for great hires, and the list goes on. He'll also not have much motivation other than accumulating stock options, vesting it, then moving on to the next startup to fool. There are exceptions but it's rare. Great marketing VPs move onto become CEOs, executive consultants, retire early and join social causes, become angel investors or VCs, start their own companies, and so on and so forth. Go to a large company and find a mid-level marketing executive (i.e., director) who wants to move up and be the primary executive or poach a fairly new ("new" doesn't necessarily mean "young") marketing VP at another startup.
* Hire for now, do not overhire. I constantly hear and see companies hiring a big company marketing VP because they already think ahead to when the startup will IPO or become the next Microsoft. Wrong. You need a marketing VP who can GET you there, not WAIT until you get there. You can always hire a Senior VP or Executive VP (there's enough title out there - don't worry) later on if you're trucking in the cash and growing so fast that a small country would not be able to hold all of your growth.
* Hire a confident executive bleeding into cocky. Unlike large companies, a startup marketing executive will have the deck stacked against them. From Day One, the score is 'World 100, You 1" and only the semi-blindly confident, passionate VP will go 10 rounds vs. 2. Unless he's such a jerk that you're forced to use the emergency exit after each working day so that you don't have to make eye contact with him, you're much better off with a wildman with fire in his belly than the professor or social butterfly of the softness and kindness variety.
* Hire someone who can attract other marketing pros. A startup has fewer marketing staff but each one has to be a lot more experienced than their large company counterparts. Startups have no processes and infrastructure in the beginning. You and your staff must build it before you can use it. Junior people do not know the first thing about building an organization. Your executive must build it and nourish it. Then, he must hire other marketing people to come and leverage it, refine it, and (again) build upon it. It's a common misperception that startup marketing types love startups because there's a lack of strict hierarchy and more freedom. If that's what a candidate says, avoid him like the plague. The answer you want to look for is the "I love marketing in startups because I love to build and building something meaningful fulfills me." Arguably, it's saying the same thing but there's an important distinction. One person is thinking from his interest and projecting inward (what can you do for me?). I can do whatever I want. The other is thinking about the startups needs and projecting outward (what can I do for you?). I'll do whatever is needed of me.
* Spend some time with the VP of marketing recruit outside of the four walls of the offices. Try to really get to know them. Standard-fare reference checks, background checks, and back-door checks aren't enough. There's a lot that paper facts will tell you but there's also a ton that'll mislead you. You'll hire the wrong people armed with the "right" paper facts and reject a lot of the right people with the "wrong" paper facts. A lot of surprising things leak out or show when you spend some quality time getting to know how a person thinks not just about business or your startup or marketing but of life, friendships, family, economy, and so on.
* Hire Smart, Fire Smart. Knowing if a marketing VP is working out well or not is very difficult. The main reason why it's tough to know is because a marketing VP is judged on the performance of their total output. This output includes the output of their marketing organization relative to the company's output over the longer haul then - say - sales or even engineering. It's a total paradox. And, it's why many CEOs have many sleepless nights. By the time you figure out that the output of the organization is not acceptable, you've already jeopardized the company and wasted a ton of money on this executive. With a sales VP, you fire them if they miss a couple quarters' worth of quotas and goals. With an engineering VP, a pattern of missing release dealines or visibly seeing terrible product instantly gives you real-time input on which to make a decision. In both of these cases, the output of their organization or lack thereof is easy to recognize. With marketing, the output takes a while to form. It's like the mini-parachute you tie to a stone and throw up in the air. You don't immediately know if the parachute will open. You don't know if the parachute was large enough to let the stone cruise down safely. You don't know if the stone will land where it's intended to land. Anyway, the only way you can know that something is not quite right with a marketing VP is to MANAGE him throughout. I don't mean micromanage him by asking for reports and status updates or getting involved with the implementation of everything - PLEASE do not do that as it's a surefire way of pushing great marketing people to quit and screw your company in the process. By manage, I mean that you need to meet regularly and engage in discussions to understand their way of thinking, decision making, planning, implementing, etc. In these meetings, stop talking or even suggesting and LISTEN.
* Last but not least, hire the RIGHT skill set. If your company is pre-market fit (ie., can't figure out if you're making something that customers want), you need to get an executive who has a strong background in product marketing. If your company is post-market fit (ie., you know there's a real market based on data and customer engagements but you're having a hard time getting the second dollar in the door and growing), you need to get an executive who has a strong background in corporate marketing. Believe it or not, in technology, it is not the same person although most will claim to be both. Every product marketing manager or director will claim to have "run" public relations, analyst relations, demand gen programs, web marketing, branding, advertising, conferences, field marketing, marcom, etc etc. ... to bag their VP of marketing job. By the same token, some corporate marketing people will claim to "know" product marketing to bag the VP job. Truth is ... both are usually not true. I've done both and hired/managed both in technology marketing. They are worlds apart. Figure out what you're looking for based on what stage your company is in ... then, you'll know who to hire regardless of whether they can actually do everything they claim to do.