Founder Operations & Customer Intelligence Lead

Skip is building an AI operating system for entrepreneurs and small business owners.

More than 1 million entrepreneurs have used Skip to find funding, build their businesses, create content, launch products, grow their online presence, and get guidance from their AI Cofounder.

We're looking for one exceptional person to work directly with Skip's founder across customer intelligence, operations, AI, and product.

This is not a traditional customer support role. It's also not a traditional executive assistant, operations, or product role.

It's a high-autonomy, high-expectation role for someone who is unusually curious, sharp, proactive, and good at figuring things out.

You won't have a tightly defined task list, and you shouldn't expect someone else to consistently tell you what deserves your attention.

We expect you to notice what others miss.

If a customer says something unusual, investigate it. If several customers encounter the same problem, figure out why. If a process is repetitive, determine whether AI should automate it. If a potential partner contacts us, understand the opportunity before escalating it. If something in Skip doesn't make sense, question it.

You'll work directly with Skip's founder, and one of the clearest measures of your success will be whether you reduce the amount he has to notice, investigate, follow up on, and manage himself.

This role will be an unusually good fit for a small number of people—and probably a poor fit for most.

What you'll own
~40% — Customer Intelligence & Human-in-the-Loop

Skip increasingly uses AI and automation to handle routine customer needs. Your job isn't to sit in an inbox answering every message. You'll own the human judgment around that system.

You'll handle situations where a thoughtful human genuinely adds value, investigate unusual customer issues instead of simply forwarding them, and understand what customers are actually trying to accomplish.

But an equally important part of the job happens after the individual conversation.

Why did this customer get confused? Is anyone else experiencing it? Is this a product problem? Is our AI getting something wrong? Is there a bigger pattern? Should we change the product rather than answer the same question again?

You'll:

• Own customer situations that genuinely require human judgment.
• nvestigate issues deeply before escalating them.
• Talk with customers by email, chat, video, or phone when useful.
• Identify patterns across customer conversations.
• Turn customer feedback into clear product findings and recommendations.
• Help improve how our AI handles customer interactions.
• Recognize when a customer message contains valuable business or product context.
• Make good judgment calls about when not to respond or intervene.
• Bring Product and Engineering evidence rather than vague feedback.

Closing support tickets isn't the goal. Learning from customers and solving underlying problems is.

~30% — Founder & Company Operations

You'll work directly with Skip's founder on whatever is most important.

One day that might mean qualifying a potential partnership. Another might mean investigating an unusual customer situation, coordinating with a grant winner, researching an opportunity, following up on something important, or making sure a project actually gets finished.

We don't want someone who simply forwards things to the founder.

We want someone who can independently come back and say:

Here's what happened. Here's what I investigated. Here's what I learned. Here's what I think we should do.

You'll gradually build enough understanding of Skip, our customers, and how the founder thinks that you can take more and more off his plate.

~30% — AI, Automation & Product Feedback

Every repetitive task should make you wonder:

Why are we still doing this manually?

We're an AI company. We expect you to use AI constantly—not simply to write nicer emails, but to research, investigate, analyze, automate, and accomplish substantially more than one person traditionally could.

You don't need to be an engineer. You do need to be deeply AI-native and curious about what's now possible.

You'll:

• Find repetitive customer and operational workflows we can automate.
• Help determine where AI should act independently and where humans should remain in the loop.
• Test new Skip functionality yourself.
• Identify confusing, broken, or underwhelming product experiences.
• Use customer conversations to discover product opportunities.
• Work directly with Product and Engineering when you find something important.
• Help evaluate and improve AI output and workflows.
• Constantly look for ways one exceptional person + AI can accomplish what historically required a much larger team.
• The kind of person we're looking for

We're much more interested in how you think than whether you've held this exact title before.

You may have worked in operations, customer experience, product, at an early-stage startup, alongside a founder, or in something completely different.

Being responsive, organized, friendly, and hardworking is necessary—but not sufficient for this role.

We're looking for unusually strong curiosity and judgment.

You should be someone who naturally thinks:

That's strange. Why did that happen?

I've seen this more than once. Is there a pattern?

Why are we doing this manually?

Does the customer actually need a response?

How do we know that's true?

What are we missing?

I don't know yet. I'll figure it out.

You'll probably thrive here if you:

• Are exceptionally curious.
• Have excellent written and spoken English.
• Have strong instincts about products and people.
• Learn complicated products extremely quickly.
• Notice inconsistencies other people overlook.
• Ask good questions without being told which questions to ask.
• Investigate before escalating.
• Can separate important signals from noise.
• Form opinions rather than merely summarize information.
• Are comfortable respectfully challenging assumptions.
• Use AI extensively and continuously experiment with what's possible.
• Can communicate naturally with an upset customer, a potential partner, an engineer, and a founder.
• Take ownership without waiting for permission.
• Enjoy ambiguity and responsibility.

We don't expect you to always be right.

We do expect you to think.

This role probably isn't for you if...

You're looking for a traditional support role where success means working through assigned tickets.

You need your manager to consistently tell you what to work on next.

Your instinct when something unusual happens is to forward it to someone else.

You prefer executing established processes to questioning whether the process should exist.

You use AI mainly to draft emails or rewrite things.

You aren't naturally interested in understanding how the entire product works.

Or you want responsibilities that remain neatly inside a predefined box.

Skip moves quickly. Our product changes constantly. This role will too.

Why Skip

You'll have unusual access and responsibility.

You'll work directly with Skip's founder and closely with Product and Engineering. You'll interact with entrepreneurs using Skip every day and often see problems and opportunities before the rest of the company does.

When you discover something important, we expect you to do something about it.

This is a role where someone relatively early in their career can take on an enormous amount of responsibility very quickly.

As Skip grows, the role can grow substantially with you.

How to apply

We know this application asks more of you than most job applications.

That's intentional.

This role offers substantially more ownership than most roles at this level. We're looking for someone excited by that—not someone looking for the easiest application process.

Before applying, spend meaningful time learning about Skip.

Visit our website. Research the company. Create an account. Use the product. Explore our AI Cofounder and other functionality. Develop some opinions.

If you haven't spent meaningful time researching Skip and using the product, please don't apply yet.

Email [email protected] with the subject:

Founder Operations & Customer Intelligence Lead — [Your Name]

Include your résumé or LinkedIn profile and answer the following five questions.

1. Why Skip, specifically?

Tell us what you think Skip is trying to build, why that interests you, and one thing you think we may be underestimating or getting wrong.

Generic answers about loving startups, AI, small businesses, or entrepreneurship won't tell us much.

We want your actual opinion.

2. Give us your mini product assessment.

Spend real time using Skip.

Tell us the three most important things you noticed.

They can be problems, opportunities, things you loved, confusing experiences, business observations, product ideas, or something we haven't considered.

Rank them #1–#3 and explain why each one matters.

Then tell us one thing you initially noticed but ultimately decided wasn't important enough to prioritize—and why.

We're interested in your judgment, not the number of bugs you can find.

3. What did we not ask you?

After researching and using Skip, tell us something you became curious about that none of these application questions prompted you to investigate.

What did you notice? Why did it make you curious? What would you investigate next? How would you figure it out?

We use AI extensively at Skip and expect you to as well. You're welcome to use AI to research, organize your thinking, or improve your application. Generic AI-generated answers, however, won't tell us much about you.

There is no perfect format for a great application.

We're hiring for curiosity, judgment, initiative, product instinct, and the ability to form your own point of view. Show us how you think.