1/ Throughout my startup career, I’ve seen many founders have an aversion to sales. This is a mistake that can kill your startup.

2/ Sales is often viewed as either a saving grace or proof that the product isn’t good enough (because it should sell itself). Neither are ever true. Some common mistakes that result in...
3/ Mistake 1: Hire a sales rep before reaching product/market fit to get your initial batch of customers. This is a mistake because founders need to work through their MVP with early adopters to truly understand what it is they’re selling.
4/ Mistake 2: Reach product/market fit, need to scale, and rely entirely on self-serve. For enterprise products that require big commitments and internal shifts, almost no product is self-explanatory enough to sell itself.
5/ Mistake 3: Make a first sales hire who isn’t scrappy enough to help mold the sales process from scratch. Some salespeople are amazing at their jobs, but not cut out to establish the processes that others end up following. This skillset is what @rdedatta calls a “sales ninja”.
6/ At Twitch, we built an advertising sales team. We tried and failed several times before finding the right sales leader who had sold into the market before. The lesson here: if it doesn’t work at first, it might be how you are doing it (not the market’s fault). Keep trying.
7/ When I talk to founders about sales, I tell them that you need to get out there yourself and do your own initial sales to learn what your customers want.
8/ @rdedatta wrote a great piece about how to get first customers and hire a sales ninja: https://t.co/MFoL36DUFI

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There are a *lot* of software shops in the world that would far rather have one more technical dependency than they'd like to pay for one of their 20 engineers to become the company's SPOF expert on the joys of e.g. HTTP file uploads, CSV parsing bugs, PDF generation, etc.


Every year at MicroConf I get surprised-not-surprised by the number of people I meet who are running "Does one thing reasonably well, ranks well for it, pulls down a full-time dev salary" out of a fun side project which obviates a frequent 1~5 engineer-day sprint horizontally.

"Who is the prototypical client here?"

A consulting shop delivering a $X00k engagement for an internal system, a SaaS company doing something custom for a large client or internally facing or deeply non-core to their business, etc.

(I feel like many of these businesses are good answers to the "how would you monetize OSS to make it sustainable?" fashion, since they often wrap a core OSS offering in the assorted infrastructure which makes it easily consumable.)

"But don't the customers get subscription fatigue?"

I think subscription fatigue is far more reported by people who are embarrassed to charge money for software than it is experienced by for-profit businesses, who don't seem to have gotten pay-biweekly-for-services fatigue.

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