TL;DR:
Zachary Stokes, through Wingman Leads and his newsletter The Outerchange, is helping operators expand beyond vending machines locations into POS systems. For operators looking to grow deal flow and relationships, this is a practical crossover worth understanding.
1) Wingman Leads: built around merchant conversations
I recently chatted with Zachary Stokes and took a closer look at what he’s building at Wingman.
The focus is clear. Wingman is built around helping operators and reps generate and convert merchant conversations into real opportunities, specifically on the POS side. What stood out is how structured his approach is around outreach, qualification, and follow-up.
For vending or ATM operators, this is directly relevant. If you’re already working on how to get vending machine locations or securing vending machines with location for sale, you’re already doing the hardest part, getting access to the decision maker.
Wingman’s approach is about making those conversations more productive and turning them into additional deal flow.
Operator takeaway:
If you’re already placing machines or building a vending route, focus on how much value you extract from each conversation.
2) The Outerchange: free tactics operators can actually use
Alongside the agency, Zach runs a free newsletter called The Outerchange.
This is where a lot of practical value shows up. It’s not general advice, it’s specific outreach tactics, positioning ideas, and ways to generate more conversations with business owners.
For operators focused on:
- how to find a location for a vending machine
- improving conversion when pitching a vending machine location for sale
- or expanding into adjacent opportunities
the content translates directly.
You can review and subscribe here:
https://www.theouterchange.com/subscribe
Operator takeaway:
If you’re already doing outreach for vending machines locations, use these frameworks to increase response rates and improve how you position your offer.
3) The overlap: vending, ATM, and POS use the same playbook
One of the biggest points from the conversation is how similar these models actually are.
Vending, ATM, and POS all rely on:
- Access to decision makers
- Understanding the business environment
- Structuring a simple, clear offer
The outreach process is almost identical. Whether you’re placing a vending machine, ATM, or discussing POS systems, the same approach applies.
If you know how to:
- walk into a business
- identify who makes decisions
- explain value clearly
you can operate across all three.
Operator takeaway:
Don’t treat POS as a completely new model. Treat it as an extension of the same outreach you already use to secure vending machine locations.
4) Where Vending Village fits in
This is where the crossover becomes actionable.
On Vending Village (https://vendingvillage.com/), operators already:
- buy and sell secured vending location opportunities
- build and expand their vending route
- access structured, verified deal flow
The same concept applies to ATM and POS opportunities.
If you’re:
- a vending operator, start identifying POS opportunities to list for sale
- a POS rep, uncover vending machine locations you can flip into paid deal flow
- or working across both
those agreements can be structured and sold in a similar way.
The core asset is not the machine or system, it’s the relationship with the business.
Operator takeaway:
When looking how to add more revenue to your business, discuss POS with your point of contact. If you are in POS, double down on those cold and warm opportunities by adding vending, ATM and Claw machines into your playbook.
Zach, thank you for your time. It was great getting to know you and learn about your experiences. We appreciate you sharing all this free game with the vending, ATM, Claw machine community!
Next step
If you’re already sourcing vending machines locations, start paying attention to what else exists inside each business.
On vendingvillage.com a rep can list for sale a vending machine location, an ATM location, a Claw machine location and as well a POS opportunity.