Insurance Product Manager Remote Jobs in Chicago, IL

Clerkie is a fintech startup on a mission to democratize financial wellness using the power of artificial intelligence. Launched in 2018, Clerkie began with an app, aiming to help the nearly 123 million underserved Americans in need of financial guidance. Since its inception, the company has expanded its services and now pairs consumer guidance with cutting-edge B2B software. By pairing the two through the Clerkie network, these tools have become the go-to resource for creditors looking to manage loan losses while simultaneously helping millions of borrowers get out of debt.

Clerkie is a remote-first company, with over 40 employees spanning 4 time zones across the United States. To date, the company has raised $41 million, including a $33 million Series A round in early 2023. Investors include leading financial and venture institutions, including Citi Ventures, Left Lane Capital, Wellington Ventures, Flourish Ventures, and Vestigo Ventures.

We're looking for a driven, curious, and collaborative Product Manager to join our small-but-mighty Product team. This role is ideal for a product builder who has shipped software before and is ready to take deeper ownership of complex systems in a fast-moving startup environment.

As a Product Manager at Clerkie, you'll operate at the intersection of technology, business strategy, and real-world financial infrastructure. You'll collaborate closely with engineers, designers, and leadership while also working directly with external partners to understand how our products perform in the wild. This role offers the opportunity to own meaningful product surfaces, contribute to product strategy, and lead initiatives that directly impact how Clerkie scales its platform and partnerships. You'll work directly with technical and non-technical stakeholders across the business, including engineering, design, leadership, and client partners. Many initiatives will involve working closely with enterprise partners and users in the debt ecosystem, helping translate complex workflows into scalable product systems.

Because Clerkie is still in build mode, this role goes beyond shipping features. You'll help shape how our product organization operates - contributing to team rituals, documentation, product culture, and the systems that allow the team to move quickly and thoughtfully. For the right person, this is an opportunity to build deep product judgment, take real ownership, and grow alongside a company early on.

• Own and lead product initiatives across Clerkie's platform, from discovery through release
• Collaborate deeply with engineering and design to shape scalable product solutions
• Translate complex partner and ecosystem needs into clear product requirements
• Drive cross-functional alignment across technical and non-technical stakeholders
• Work directly with enterprise partners to understand workflows and product opportunities
• Define priorities, manage trade-offs, and help shape product roadmap decisions
• Lead product discovery, experimentation, and iteration across multiple initiatives
• Support the continued evolution of Clerkie's product systems, rituals, and documentation
• Contribute to building a strong product culture within a small, highly collaborative team

• Shipped high-priority product improvements for enterprise partners while pressure-testing our platform to support increasing scale
• Partnered directly with our SLT to scope and prioritize key initiatives across multiple product surfaces
• Led the development of enterprise sandbox demos with Design and Engineering that helped unlock major deals
• Contributed to shaping Clerkie's evolving product strategy and roadmap across both consumer experiences and the Fiber platform
• Improved our internal product knowledge base making documentation clearer, more useful, and easier for new teammates to navigate
• Helped onboard a new member of the Product team and refined internal product rituals to keep the team operating smoothly
• Joined our team hackathon to explore new product ideas and experiment with early concepts for future platform capabilities
• Spent the day on a private ranch in Jackson Hole horseback riding, axe throwing, eating outside a Michelin Star chef's table, roasting smores under the stars, and celebrating your latest hackathon win
• And so much more. Startup life moves fast and we're just getting started ????

• Experience building and shipping software products in collaboration with engineering teams
• Strong systems thinking - you're able to break complex workflows into clear product solutions
• Technical fluency - you're comfortable discussing APIs, data flows, and system architecture with engineers
• Ability to translate real-world problems into clear product requirements and prioritized work
• Excellent written and verbal communication skills across both technical and non-technical audiences
• Strong ownership mindset - you take responsibility for outcomes, not just tasks
• Ability to operate in a fast-moving startup environment where priorities evolve quickly
• Comfort working independently in a remote-first team

• Experience working on SaaS platforms, infrastructure products, or developer-facing tools
• Familiarity with fintech, financial services, or regulated industries
• Experience building products that integrate with external systems or enterprise partners
• Background in engineering, computer science, analytics, or another technical field
• Experience working in early-stage startups or high-growth environments
• Curiosity about financial wellness and technology that improves people's lives

• ???? Salary range: $120-150k 
• ???? Equity
• ???? Remote-first role (US only)
• ???? Medical, dental, and vision insurance
• ???? 401(k) + retirement benefits
• ???? Paid time off + annual company retreat
• ???? Company laptop + home office stipend
• ???? Collaborative, values-driven culture

We believe in a two-way interview process that helps us get to know you—and helps you get to know us.

1. Application (async)
2. Intro Call w/ People Team (20–30 min)
3. Take-Home Challenge (async over 1 week)
4. Take-Home live Presentation (1 hour live review with Product Team)
5. Technical Deep Dive w/ Product Leader (90 min)

Before we extend any offers, all candidates must successfully complete a standard background check in addition to a reference check. These checks are conducted in tandem to ensure a safe, secure, and compliant environment for all Clerkie team members and stakeholders.