First, let’s set some boundary conditions. This post is targeted at tech startups that are looking for an execution focused, front-line sales person. Filepicker.io is a good example of this kind of a company. This post is not about bringing on a business co-founder or hiring your first senior business person. I have seen similarities between hiring a rank-and-file salesperson and a VP of sales but I expect that your Angel investor or VC firm will guide and coach you through that process.
Do you really need a sales person?
Ask yourself this question before you start spending energy on finding a sales person. Tech heavy startups with 2-3 technical co-founders have a tendency to lump all non tech activities into the ‘business’ bucket. It is worthwhile sitting down as a team and asking yourselves if what you need at this stage of the company is sales or business development or marketing. Here is an earlier post on this topic which could help guide that discussion. 
Source: sacks08, Flickr creative commons
If you are in the consumer web business, then though you say you want a sales person what you mean is a marketing person and a biz. dev. person for partnerships. If you are in the enterprise software business, then you absolutely need a sales person. One word of caution: beware of mistaking biz. dev. folks with sales folks. If you looking for a sales person then do not settle for a biz. dev. person. Biz. dev. folks do not carry sales quotas and hence operate at a different rhythm. Their world involves building relationships and a cadence of activities that yield longer term results. These efforts take longer and more engineering/legal bandwidth. If sales is what you want, then you got to have someone on your team who has carried a sales target before, who dreads the thought of missing it and will work his ass off to build a pipeline of prospects.
Where can I find a sales person?
“Hire a person with a lot of hustle” is the common refrain. Where do you find this profile of a person? A good place to look for: inside sales organization of larger companies like Salesforce.com or LinkedIn. Inside Sales is “remote sales,” or professional sales done remotely whereas outside sales/traditional Field Sales is done face-to-face. 
Source: kirainpdx, Flickr creative commons
Inside sales people tend to be younger-early 20s. They have been trained in cold calling and selling, used to getting rejections from prospects on the phone, and extremely good at following up warm leads. This is precisely the kind of sales role in an early stage startup. But best of all, inside sales jobs have a high burn rate, so you will find a lot of awesome, sharp people who are looking to move on. A startup gig that gives them autonomy, equity and the ability to do interesting work is extremely appealing for a young sales turk. An often overlooked argument against hiring outside sales reps is that an early stage startup can’t afford a roaming field force. It’s way too expensive.
Who to hire?
Caveat: A few of the suggestions below may appear abstract but hey…hiring is an art.
1.Knowledge: You want someone with domain knowledge. Domain knowledge has 2 components-industry knowledge and product knowledge. Ideally you want someone who has sold similar products into the same industry (advertising, recruiting, developers etc.) as your business because the contextual knowledge that he brings to the table will help him ramp up faster. If you can’t find that, then err in favor of industry knowledge. Based on my experience, its way easier to learn how to sell a new product into a known industry than the other way round. Often you will hear arguments that suggest you want to hire a sales guy/gal with a rolodex of contacts. It is awesome if you can find one, but the chances are that you won’t. I have found that the intersection set between smart/thoughtful sales guy/gal and those with a rolodex is pretty small. In such cases err on the side of the smart one. Your angels and your VCs will have enough connections to help out.
2.Skills: check to make sure that the person has account planning skills. Account planning for sales is the equivalent of system architecture for engineering. It lays out a hypothesis for how the sales person is going to go from no revenue/customers to $X in revenue/customers in Y# of months. The focus of an account plan includes good stuff such as: which customers to go after? What are the buying units that are relevant to the startups business? Who are the key stake holders and how will you influence them to consider you? What value proposition will you take to them? What is the calendar of activities etc? 
Source: Guy schmidt, Flickr creative commons
A good way to assess if he has these skills is to test this through the interview process. Just as in technical interviews you would expect a candidate to write code to provide his technical chops, asks the candidate to develop a sales plan if he were hired. But unlike a technical interview, give the candidate a few days’ time to come up with a plan. This will involve researching the market, doing some preliminary analysis and would require some back and forth for the candidate to understand how your product would fit with the market. This is also a great filter for weeding out the uninterested who are looking for a ‘job’ rather than something more purpose/mission driven.
3.Attitude: check to make sure that the person is a renaissance sales person as opposed to a coin operated sales person. Khosla Ventures has a great article that covers this topic. A renaissance sales person is self-sufficient, adaptable and mode adept at tailoring the message to the needs of the audience he is selling to. 
Source: George Eastman House, Flickr creative commons
Given that early stage startups constantly modify, adapt and change their value proposition, you will need a sales person who is comfortable with this ambiguity. In fact the best sales guy/gals that I have seen are those that make up their own product roadmap of features that aren’t already built and work extremely closely with the engineering team and the customer to align the timelines.
So in summary, before you start looking for a sales person make sure that your business actually needs sales efforts. At Filepicker.io we had this conversation among the founding team and the learning from articulating our requirements was incredibly helpful. Look for inside sales reps who have sold into your target market before and have account planning skills. Finally, given the amount of change in a startup’s product roadmap, you want to hire a renaissance sales person instead of a coin-operated sales rep.
Follow the discussion on HN.
-Anand
Filestack is a dynamic team dedicated to revolutionizing file uploads and management for web and mobile applications. Our user-friendly API seamlessly integrates with major cloud services, offering developers a reliable and efficient file handling experience.
Read More →