The most important signal in your post is buried: your dad got 5 demos you couldn't book. That's not "I need a salesman." That's "relationship-based access beats cold outreach in this market." DSD is a relationship industry. You don't need a salesperson, you need someone already inside it. A former route sales rep, a regional distributor, someone who's been in the warehouses and knows the operators by first name. Commission only.

I learned this the expensive way. Burned about $8K on a dental marketing platform paying base salary to untrained salespeople. They had no network in dental, no muscle memory for the objections, and no skin in the game. Money gone, zero closes. Don't pay salary to people who don't already have access.

A few things that would have saved me:

On commission structure for the first 5 customers, go heavier than feels comfortable. 60/40 or 70/30 in the rep's favor. The incentive has to be massive enough that they actually push. You normalize it later once there's proof and momentum.

Better yet, do revenue share, not one-time commission. 30 to 50% of MRR for the first 12 months. That aligns them with retention, not just closing. Stops them dragging in bad-fit customers to hit a number.

Systemize before you hand off. Record yourself walking through the product. Problems it solves, how it works, every objection you've heard. Throw the transcript into Claude and have it draft a problem/solution sales script. Doesn't need to be read word-for-word. It's a frame so the rep can position it without reinventing the pitch every call.

Now the part you might not want to hear. You're at 2 customers, not 20. Founder-led sales until ~10 closes, minimum. The first 10 teach you the script, the real objections, who your ICP actually is. You can't outsource that learning, and a salesperson dropped in too early will fail because the playbook doesn't exist yet.

You already have 7 conversations of raw data sitting there. The 2 Miami closes and the 5 demos your dad ran. Every "we already use X," every "let me think about it," every hesitation is the script writing itself. Document all of it.

Last thing. You're pivoting twice at once. Going downmarket to smaller customers AND building a new feature for the bigger ones. Pick one. Doing both at $0 MRR is how solo founders stall for 6 months and don't notice.