Solo technical founder. Should I find a salesman or solo it?

I’m a solo technical founder bootstrapping a software in the direct store delivery SMB industry (DSD). I’m based in Miami, FL. I decided to launch in LATAM as I thought it would be an easier place to start due to money.

I hired a salesman in LATAM but it didn’t work out. Made the mistake of offering a base salary, as I should’ve just offered 50/50 commission. Also customers in those countries generally don’t really see the value of software. As someone once said, “LATAM is great to start in but a horrible place to be stuck in.”

Right now I’m going back to sticking with Miami. But I need help with executing the sales part. I can do sales myself, but I have limited experience in it. I’ve managed to close 2 customers (Miami) myself but it was a slow process since I’m the only employee.

I also had my dad help me out with sales at some point recently and for 5 customers I couldn’t book a demo with, he was able to get demos with them. Which obviously made me realize I can do it myself but I won’t be the best at it.

Need advice on how to approach this next season of my business. I’m currently still at $0 MRR as my initial launch in LATAM failed. Also the 2 customers in Miami were a little too big and I didn’t have a feature they needed, So I’m starting smaller with a list of prospects I found while hunting on the street. And yes I’m going to start building the feature the bigger companies needed.

Solo technical founder. Should I find a salesman or solo it?
byu/EngineeringLifee inEntrepreneur

Posted by EngineeringLifee

aslamnd on April 28, 2026 2:53 pm

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.

6 Comments

stressfreepro on April 28, 2026 2:20 pm

saw a post on r/HustleHacks about exactly this. the difference between hobby money and real income is usually systemizing. track everything from day 1.
DarkIceLight on April 28, 2026 2:37 pm

50/50 is WAY to high if he truly does nothing else than sale.
kunalkhatri12 on April 28, 2026 2:37 pm

The fact that your dad booked those demos proves you have a product people want, you’re just overthinking the pitch.

Don’t hire a salesman yet; they can’t sell a product that is still finding its legs, but the person who built it can.

Keep hitting the pavement in Miami, close the next five deals yourself to master the Why, and use that raw feedback to finish the features that actually scale.
Specific-Age7953 on April 28, 2026 2:42 pm

ran into this exact thing. the problem usually isn’t commission vs salary
it’s handing sales off before you’ve personally closed 20+ deals yourself. until you know exactly what questions buyers ask and why they say no, you can’t train or manage a salesperson who’ll actually close. do the sales yourself first.
aslamnd on April 28, 2026 2:53 pm

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.
Acceptable_Maybe_198 on April 28, 2026 2:54 pm

You’re taking the wrong lesson from your dad.

He didn’t prove you need a salesperson. He proved you need a better way to get meetings.

You’ve closed deals, so ‘sales’ isn’t the problem. Conversations are. Fix that first.

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