[realsharkymark]

As a VP of Sales selling dev tools, I noticed:

1. As mentioned already, if devs aren't already using it, it's an uphill battle to sell.

2. Having your product as OSS helps since it reduces barrier to entry - devs and being using your product without having to contact sales.

3. Large enterprises, e.g., Fortune 500/Global 2000, spend money to reduce risk, cost and improve productivity (and other reasons) - as long as devs will use the tool. Startups, smaller companies would complain about spending even a dollar (probably because so many tools are OSS)

4. Target the centralized dev intra leadership and team would buy and support other dev tools. A junior sales mistake is giving free sales resources (e.g., demos, trial support) to a distributed team or devs trying your product - they probably will never buy since they didn't have authority, and all you did was provide free OSS support to get them running. Coaching sellers to avoid this is key - steer these types to docs and community.

5. Sell the value of support. Sales will only help if speaking with a qualified opportunity with authority and budget - otherwise good luck in the docs and community. In large enterprises, that is not a strategy.

6. And to the sea of sellers who think they can cram down large contracts - get the initial pilot or purchase successful - help demonstrate metrics of its value - .e.g. productivity etc. and put it in an easy-to-consume way for real decision makers to understand. Then you are more likely to take down larger investments. And yes - even before that initial deal, explain a license model and examples of how this scales to be affordable and not linear. You look like the JV squad if you do otherwise and will not know why they stopped returning your calls. You get one chance to make a viable economic impression if deployed site-wide. Unless you work at massive software companies where you can cram down large purchases due to enterprise agreement quirks and holding customers hostage to agree to software they may or may not use. e.g., company heavily uses one product so vendor stuffs other products in the renewal.