The most effective way to do this is through customer development. Customer development is a non-sales conversation with potential customers to get a feel for their roles, goals, and pain points. Don’t go for the sale during these conversations. Customer development is about applying a hypothesis to your business model to validate your ideas rather than assuming they are true. 1) Start with a hypothesis of your Ideal Customer Profile, why you think your product will be necessary for their situation, etc. 2) Set up informational interviews with these people. You’ll be surprised how receptive people are to conversation if you take a consultative approach with a lead asking for feedback and advice rather than a sale. 3) Begin the interview with questions about their company, then dig into questions about the individual’s role, goals, pain points, and specific questions about what pains your product may be able to relieve (i.e. how you handle employee on-boarding if that is your product). This is about deep customer insights vs. selling your product. -Ask open-ended questions instead of yes or no questions. 4) Take the feedback and iterate on your ideal customer profile hypothesis, refine interview questions, repeat 10+ times, and record all data in a uniform way. 5) Make product or messaging tweaks after these conversations.

As a small company with $40k ACV, you should hire the rep to be in your office. The experience they will get being around your team everyday is very hard to replicate as a remote employee. If you need to have boots on the ground to close deals, send your rep to travel 20-30% of his time to visit customers in person.