Senior Product Lead (AI)

**Read this first: **We review every application ourselves. To be considered, please email careers@helloskip.com with the requested materials at the bottom of this post. Spend time with Skip. We want to hear what you noticed, what you questioned, and what you would make 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 exceptional Senior Product Lead to work directly with the founder, design and engineering team. This isn't a roadmap manager. It isn't a feature coordinator. It's a product leadership role for someone who loves building products, sweating details, simplifying complexity, and shipping quickly — and who becomes genuinely obsessed with understanding the product, the users, the data, and how every part of the experience can be better. Every week you'll debate product decisions, work closely with designers and engineers, and help shape how millions of business owners use AI. **What You'll Work On** * AI experiences and autonomous workflows * Onboarding and activation * Growth and retention loops * Memberships and monetization * Marketplace and commerce * Dashboards and analytics * Mobile and web experiences **You Might Be a Great Fit If You...** * Have exceptional product taste * Are obsessed with getting better and becoming exceptional at your craft * Go deep before forming opinions — you investigate, use the product, talk to users, look at data, and challenge your own assumptions * Think deeply about user behavior and psychology * Can simplify complicated products * Love working directly with engineers and designers * Care about every pixel—but also every metric * Ship quickly and iterate constantly * Are AI-native in how you work and have experience building AI products or AI-powered workflows * Think like an owner * Notice problems others miss and take initiative to understand and solve them * Have strong opinions, but change your mind quickly when the evidence says you're wrong **Bonus Points** * Startup experience * Experience with SMB software, fintech, marketplaces, or AI * Built products from zero to one—or significantly improved products used by millions * Strong writing and communication skills **Why Join Skip** * Build AI products used by more than 1 million entrepreneurs * Work directly with the founder * High ownership and autonomy * Ship every week * Competitive salary plus meaningful equity **Compensation** * $120,000–$180,000 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 careers@helloskip.com Subject: Senior Product Lead – Application **Include:** * Resume or LinkedIn * Examples of products you've helped build * Spend time using Skip before applying. Tell us one thing you think we do exceptionally well, one thing you would change, and why. * Tell us about a product you personally drove from insight → decision → shipped result. What changed because of your work?