I wrote a while ago about when and how the founder in a startup should decide that he or she no longer needs to be making every sales call. My focus then was on the importance of understanding and quantifying your product's state of development and relative maturity. The idea is that until you know exactly what you're selling --by doing it over and over again and not as a one-off-- and know that it can be sold consistently by others, you'll need to stay in the field and keep selling.
That's because your product is still being developed on the fly and continually redesigned/reconfigured to better suit the real requirements and demands of the customers. And, the fact is that ultimately only you can make the critical design and development decisions and you'll do a much better job of that if you are hearing it directly from the end users and not from a bunch of whiny salespeople. But once you do reach that point, you need to kick yourself upstairs and focus on other things. I encouraged CEOs who spent too much effort selling to better use and optimize their time. I suggested that they needed to find competent sales managers and others who could tee up just the right meetings for them - not "opening" meetings which are a dime a dozen - but "closing" meetings where the deals got done.
Finding these sales meat-eaters isn't easy; they are the hardest hires for any startup, but it's absolutely critical to have them onboard if you're going to build a viable business. There's no more challenging job than being the person who has to fire people. Everyone else gets to talk about what a tight-knit, stick-together group the company is (just like a "family" of friends), but the sales manager is the one who has to deliver the bad news over and over again. This essential role doesn't win any popularity contests and - just to be clear -most CEOs suck at it. They're more focused on leading the charge forward and being the business's biggest cheerleader rather than handing out monthly pink slips.
When you're hiring sales talent, you need to also be careful to avoid the empire builders. There's a whole generation or two of sales management types whose experience is in large organizations. I have found fairly consistently that they are the wrongest guys possible for a startup because they grew up in a system where they measured their value and their success by the sheer number of people they managed rather than the results that those folks delivered. Nothing kills a young business faster than bloat and bureaucracy and having too many sales people sitting on their hands and not selling is the worst kind of poison. So be careful what you wish for and who you hire for this critical job.
And, at the other end of the spectrum, I'm also seeing more and more startup CEOs who discover way too soon that they don't like the wear and tear, the travel, and the rejection that are all crucial parts of selling a new product or service. So they retreat, thinking they can run their businesses while they're sitting on their butts behind a desk back in the office. That's not how this game works; that behavior is a formula for failure. You may not be an extrovert, you may not be the world's greatest storyteller or presenter, and you may not even know the technology that underlies your business as well as half the other people in the company. You are, however, the boss and today that fact alone means a lot, at least to the people who make the final purchasing decisions. Remember that these buyers are typically older than you, they grew up in strictly hierarchical systems where titles count, and they need to be made to feel important and respected if they're gonna sign off on your deal. No offense to any of the members of your team, but they don't want to deal with the monkey-- they need to see the organ grinder. That's you.
Why? For all the obvious reasons. (1) People don't really care how much you know until they know how much you care. Showing up shows them that you actually do care. (2) Startups are notoriously scattered and in a hurry. Focus and attention to detail are scarce commodities and the customers want to know that you personally are connected, paying attention, and directly engaged with their business, their concerns and their problems. And finally, (3) they want to hear it from the horse's mouth. Not second hand. They want commitments and assurances from you (since they know that the sales guys will tell them anything and promise them the world) that you will stand up for and stand behind your product or service and make good on whatever they've been promised. The buck always stops with you.
None of this is very tough. You just have to say what you're going to do and do what you said you would and everything will be hunky-dory.