How technology entrepreneurs should hire sales people

In the initial days of your startup (when you are less than 5 customers) I believe the founders should do most of the selling. Whether it is to investors, potential employees, prospects, the founder(s) knows the solution and the market need best.

So what happens after you have exhausted your personal contacts and you need to ramp up sales? As most founders do, you look to hire your “first” sales person.
There are many kinds of sales people, so there is not one answer to the question “Who should we hire?”. Broadly:
1. The Process jock (aka, follow steps in sequential order). This person typically has been at a large company in your space. Has listed over 10-12 different “sales methodologies” that she’s trained in – Spin Selling, VITO selling, etc. She will ensure that 100 leads will be tracked in your SFA tool, gives you great reports and also can help hire (albeit in a limited fashion).
Hire this person if: you have figured out the exact market,  the target account list and you need someone to scale up operations. This person is not good at being an evangelist or at consultative selling or vision selling. If your product is still one of those that most people dont “get” immediately, dont hire this person.
2. The Hustler (aka lets do a deal). This person typically has been in services organizations or has sales positions in multiple startups. Their resume looks like a menu from Subway. Some main companies, but lots of deals listed.
Hire this person if: You need deals of all sorts. This person wont be able to hire or scale your sales operations. She might get you into deals that are not a perfect fit with your value proposition, but will get you deals.
3. The Leader (aka high level sales executive). This person has at least 2-3 Vice President titles on their resume. They have multiple sales people that are connected to them on their LinkedIn profile and typically over 500+ connections. Their resume talks less about # of quarters they consistently delivered on their quota, but more about the # of people they managed, # of sales offices run etc.
Hire this person if: The product fit to your market exists and you need to build a large sales organization fast. You will have to hire a marketing head to ensure this person has a customer presentation, a demo, a proposal template, etc. 
4. The Industry Maven (aka have a great rolodex): This person has been selling to the same companies and industry for over 15 years. They would have represented multiple companies (sometimes even competitors) during their career, but their coverage of titles sold to would be small. They have a few good relations with customers they have sold to and are looking to leverage them.
Hire this person if: You find that a certain verticals or geographies have more of a need and are expressing more interest in your solutions than others. This person is good if you have a limited set of initial target customers and many of them are part of a clique (those who buy if the others buy).
5. The Relationship manager (aka technical light-weight). This person builds great relationships. They tend not add too many folks as connections to their LinkedIn profile. During your interview, they will consistently talk about the key relationships they have with clients, and how they have known them for years.
Hire this person if: Your product does not need too much pre-sales (technical) support to sell. These resources tend to be fairly light with technology and the latest trends, so you will need to hold their hand more than necessary for the first few deals.
I tend to hire the Hustlers first, then the Relationship folks and finally the process and Executives. Have you hired any of these types of sales people? What has your experience been?

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