Founding Operations Manager, AI and Outbound… at Upwind · Remote

I started Upwind because of a pattern I kept running into as an angel investor and advisor. I was meeting with early-stage founders constantly, and almost all of them had a real product and a real market. What they did not have was enough conversations with customers. Cold email had stopped working for them. Meanwhile the phone had gone the opposite direction, wide open, and almost nobody was working it well.

So I built the thing those founders needed. Upwind is a done-for-you outbound calling agency. We source and train the callers, we test the scripts and the lists, and we use AI to figure out who to call, when to call them, and what to say. Over 46% of interested prospects book a meeting on the spot, and the average client sees $412K in annual pipeline value.

The business is growing fast. We have nearly tripled our client base in the last two months, and I can no longer run all of it myself. That is why this job is open.

What you'll do

You will run the operation. From your first week:

• Build and manage the calling team. You will recruit callers, train them, set the quality bar, run the QA, and let go of the ones who do not hit it.
• Own the AI layer. We run agents for list building, prospect research, call analysis, script iteration, QA, and client reporting. You will build that stack, break it, and rebuild it. I am not talking about using ChatGPT occasionally. I mean designing systems where the agents do the work.
• Optimize the campaigns. You will own the numbers on every account: connect rate, conversation rate, meetings booked, show rate. When something stops working, you will find it and fix it.
• Keep and grow the clients. Retention and expansion are the scoreboard here, and they are what your upside is tied to.

Who I'm looking for

• You have cold called yourself and you were good at it. You know the difference between a real conversation and someone reading a script at a stranger. This one is not negotiable.
• You are obsessed with AI. You build things with it on your own time, you have opinions about which model to use for what, and you have automated things nobody asked you to automate.
• You have managed people before, or it is obvious that you are ready to.
• You move fast and you own outcomes without needing much direction. This is an early-stage operating job, not a seat inside a system that somebody else already built.

Compensation

The base is $50K. The range on this listing reflects what I think a strong first year actually looks like, because the rest is performance pay tied directly to client retention and expansion. That part is uncapped, so if you grow the book you will clear the top of the range. I want to be straight about the tradeoff. The base is a startup base, and the reason the upside is real is that this company's revenue depends almost entirely on how well this job gets done.

Working with me

You will report to me directly. I am a serial entrepreneur who has built and sold companies, and I spend the rest of my time investing in and advising early-stage teams. You will get a close look at how deals actually get done and how companies actually get built, and you will get a founder who is in the work with you rather than reviewing it from a distance.

How to apply

Please do not send a cover letter. Just answer two questions:

1. Tell me about a cold call you made that worked, and why you think it worked.
2. Tell me about something you have built with AI. What does it do, and what would you fix about it?