Top Tech Jobs & Startup Jobs in Chicago, IL

Develop product-building skills while working directly with the CEO to build or scale new product verticals. Responsibilities include identifying opportunities, executing growth strategies, navigating operational complexity, and collaborating across product, growth, operations, finance, engineering, and data. The role offers broad exposure to startup functions and may lead to future product or commercial leadership opportunities.

Build and scale new product verticals under direct mentorship from the CEO. The Product Manager will identify customer pain points, develop strategies, execute initiatives, and collaborate across product, growth, operations, finance, engineering, and data. The role offers broad exposure to startup operations and potential progression into product or commercial leadership.

Leads partner ecosystem growth by managing strategic relationships, developing business plans, identifying new partnership opportunities, negotiating deals, analyzing performance data, and resolving operational issues. Collaborates with product, operations, data, and sales teams to deliver scalable outcomes and reports to the VP of Partnerships.

Manage and grow strategic partner relationships, develop business plans and OKRs, identify new collaboration opportunities, negotiate mutually beneficial deals, analyze performance data, deliver actionable insights, and resolve operational issues. The role partners with product, operations, data, and sales teams to execute partnership strategies and accelerate business growth.

Lead business development and partnership growth by managing strategic relationships, developing partner business plans, identifying new opportunities, negotiating mutually beneficial deals, analyzing performance data, and resolving operational challenges. Collaborate with product, operations, data, and sales teams to execute partnership strategies and accelerate organizational growth.

Build and grow Jerry’s organic presence across Reddit, Quora, YouTube, and TikTok. Develop channel-specific community engagement playbooks, grow trusted subreddits, and create scalable content and engagement strategies. Partner with Growth and Content teams to maintain consistency, while measuring sentiment, share of voice, referral traffic, and LLM citations. The role requires authentic platform-native communication, SEO and LLM knowledge, and experience making complex or stressful consumer categories relatable.

Own end-to-end analytics for a business unit spanning growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; surface actionable insights; and influence stakeholders’ decisions. The role requires independent data work, strong analytical judgment, clear communication, and ownership of ambiguous, high-impact initiatives.

Own one of Jerry.ai’s emerging 0-to-1 product bets, such as home, motorcycle, boat, RV insurance, or property-tax services. Identify customer needs, analyze quantitative and qualitative data, prioritize high-impact opportunities, build and launch products, gather feedback, iterate, achieve product-market fit, and scale successful offerings. The role requires strong ownership, consumer product judgment, analytical thinking, and comfort navigating complex regulatory and operational challenges.

Create authentic, educational Reddit content about automotive and financial topics for relevant communities. Write long- and short-form posts, engaging replies, SEO-optimized content, and narrative formats that build trust and organic reach. Translate complex insurance, vehicle maintenance, and purchasing topics into clear, useful prose while collaborating with Content, SEO, and Product teams. Requires strong Reddit fluency, copywriting experience, community awareness, and resilience to public and internal feedback.

Manage Jerry’s Reddit presence across brand-owned and relevant automotive, financial, and consumer communities. Create educational posts, guides, and visual content; establish community voice and engagement practices; handle reputation and crisis responses; track karma, sentiment, referrals, share of voice, SEO, and LLM citation impact; and relay customer insights to Product and Content teams.