How to Sell in an Unknown Market?

In this case you'd make the approach more internal to you, your service/product, your perspectives, and so on:

- You aim for what seems like a reasonable standard of quality in the first place

- You actively gather & respond well to customer feedback. Provide a personal touch if it helps you gather feedback & deliver quality.

- You develop a superior perspective on the dynamics of your own product: How & when it works well

- You start to place your customers into theoretical groups

- You test the dynamics (price reaction, product change reaction) of each group

- You rank the groups by most-interesting and refine the ranking over time, asking how this information informs your pricing & development plan moving forward

- You tighten this decision-making loop, making it fairly frequent (usually weekly at least) & ask how it's working out for you, and what needs to change

You can be doing this with < 10 customers if you want. Good luck to you

Right now I sell to founders, but to build a viable business I need to sell to HR (HR SaaS). I don't know much about HR. I've built a team, I've contemplated then written a ton of policies, I've dealt with HR related issues, but I've only done it in one company, and I didn't hire any experienced HR people to help. Here is how I am approaching the problem.

1 - I joined all of the relevant Facebook and Reddit communities, and spend about 30 minutes per day just reading HR problems/solutions/discussions.

2 - Every time I talk to an HR person during sales / customer success, I ask them where they learn from, what their career path has looked/looks like, how purchasing decisions are made, etc.

3 - I've begun searching and listening to the podcasts my competitor's founders appear on.

4 - I'm going to start a local meetup, hopefully expand it into a regional conference.

TL;DR: Join communities and consume content created by your target audience.