Product Intelligence Lead (AI & Data

Read this first: We review every application ourselves. To be considered, please email [email protected] with the requested materials at the bottom of this post. Spend time with Skip. We want to hear what you noticed, what you questioned, what you investigated, and what you think we should understand better.

About Skip
Skip is building AI for entrepreneurs. More than 1 million entrepreneurs and small business owners use Skip to find funding, build websites, create business plans, generate content, sell products, and grow their businesses.

Our mission is simple: Build AI that helps millions of entrepreneurs and small businesses succeed. Skip wants to be the largest company in the world helping entrepreneurs and small business owners.

About the Role

• We're looking for an exceptionally smart, analytical, and curious person to work directly with the founder, product, and engineering team.
• This isn't a traditional data analyst role. It isn't a reporting role. And it isn't a traditional product manager role.
• Your job is to find important things about Skip that we don't know yet, figure out why they're happening, and turn what you learn into better products and decisions.
• You might come from product, data science, AI, engineering, growth, economics, research—or somewhere completely different. We care much more about how you think than your current title.
• You'll have access to a large and growing dataset across entrepreneurs, businesses, product usage, subscriptions, customer conversations, funding activity, content, AI interactions, and more.
• Sometimes we'll give you a question to investigate. More importantly, we want you to notice questions nobody has asked yet.

What You'll Work On

• Product and behavioral data across millions of user interactions
• Customer feedback and customer intelligence
• Growth, activation, retention, and monetization
• AI product quality and performance
• Experiments, cohorts, patterns, and anomalies
• Funding and grant behavior
• Business and entrepreneur success signals
• Internal analytics, models, and intelligence systems
• Turning qualitative feedback into quantitative investigation
• Finding product opportunities and problems before they're obvious

You Might Be a Great Fit If You...

You don't need 10+ years of experience for this role. We'd rather hire someone with exceptional analytical ability, curiosity, and initiative than someone with the perfect résumé.

• Are exceptionally analytical and intellectually curious
• Naturally ask “How do we know?”
• Go deep before forming opinions—you investigate, quantify, compare, and challenge your own assumptions
• Think naturally in denominators, cohorts, distributions, causality, and root causes
• Can take a messy question and figure out how to answer it without someone giving you step-by-step instructions
• Are comfortable working directly with data and SQL
• Have strong statistical and experimental reasoning
• Can connect qualitative customer feedback with quantitative product data
• Distinguish observations, hypotheses, correlations, and conclusions
• Notice patterns, inconsistencies, and questions others miss
• Don't just report what happened—you figure out why it happened and what we should do about it
• Are comfortable challenging the founder and team when the evidence points somewhere different
• Communicate complicated findings simply
• Move quickly without sacrificing rigor
• Are AI-native in how you work and constantly use AI to make yourself more capable
• Think like an owner and proactively investigate things because they matter—not because someone assigned them to you

Bonus Points

• Product, data science, AI, analytics, engineering, economics, or quantitative research experience
• Startup experience
• Experience with large behavioral datasets
• Experience with SMB software, fintech, marketplaces, or AI
• Built internal analytics, experimentation, or intelligence systems
• Have personally discovered something in data that materially changed a product or business decision
• Can prototype or build lightweight tools yourself
• Strong writing and communication skills

Why Join Skip

• Work with data and products used by more than 1 million entrepreneurs
• Work directly with the founder
• Investigate important questions with significant autonomy
• Influence what we build and how we operate
• Work closely with a fast-moving product and engineering team
• High ownership and autonomy
• Competitive salary plus meaningful equity

Compensation

• $70,000–$120,000 USD + meaningful equity, depending on experience, location, and impact
• Flexible PTO
• Remote-first, with the option to work in person with members of the team in New York, Miami, and São Paulo
• We care far more about finding an exceptional person than where you sit

How To Apply
Email [email protected]
Subject: Product Intelligence Lead – Application

Include:

• Resume or LinkedIn
• Tell us about something important you discovered in data that nobody explicitly asked you to investigate. What did you notice, how did you investigate it, and what changed because of it?
• Spend time using Skip before applying. Tell us something you noticed that you would want to investigate further. What questions would you ask, what data would you look at, and why?