An upside of manually processing quotes is striking up conversation with potential customers. If a quote doesn’t convert to a policy, I get to ask why. Now I know the number one reason I lose sales.

Now I’m into With Jack’s full second month of trading… and it’s hard. I’m realising just how challenging it is to market and sell insurance, especially as a newcomer to an established industry.

If it was easy everybody would start a business. Last month I launched With Jack, so what issues have I faced with the first month in business?

Last week I launched my insurance company, With Jack. I’d been in closed beta for 3 weeks prior, sourcing feedback from people who’d volunteered to test the onboarding process (thanks, people!).