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Re:Lessons we learned while bootstrapping by the_bear on Tuesday November 28, 2017 @01:19PM (#15799855)
Do you have to target enterprise customers rather than small businesses? Enterprises have very complicated decision-making processes that can be hard to navigate if you're not experienced, and even harder if you don't already have traction.

Small businesses on the other hand will normally try out a demo of the product and decide on the spot if they like it or not. They aren't all that way, but if you talk to 50 10-person businesses, at least a couple of them will probably be willing to buy on the spot if your product solves a problem for them at a reasonable price.

Go get some of those tiny customers even if they're not profitable for you, and then later move upmarket to the enterprise clients you really want. Or do what I do and just stay focused on small customers indefinitely because they're so much better to work with.

Re:Lessons we learned while bootstrapping by mlevental on Tuesday November 28, 2017 @01:36PM (#15800034)
it's true that one of the difficulties has been finding who exactly in the larger organizations to pitch the product to. early on we figured out that it should be people with a budget (i.e. those directly in charge of p&l) rather than executives or product teams but we've actually been "gatekept" from getting access to those people.

but this is a good idea. i've tried cold outreach but to larger organizations. i'll try reaching out to smaller (tiny) customers. thank you

Re:Lessons we learned while bootstrapping by ju-st on Tuesday November 28, 2017 @02:09PM (#15800339)
I had success with pitching to consultancies. They have the right contacts and are probably interested in re-selling your cool and innovative product. Contact details of the right managers are usually published on their website because they want new customers to call them (but no one is stopping you to contact them for pitching :)).
Re:Lessons we learned while bootstrapping by dboreham on Tuesday November 28, 2017 @05:11PM (#15802338)
In general I've realized over the years that you are much better off if you can somehow get the customer to come to you, asking for your product or service (vs trying to "sell" to them). Of course easier said than done, but this is the essence of marketing -- perhaps make some noise in the right places so interested customers become aware of you.