Operational Specialist

Stridekick is a B2B2C preventative health platform that combines gamified health challenges with a curated marketplace of health and wellness products. Employers and small groups use our platform to get their teams moving together through fun, competitive challenges — and our shop marketplace helps users invest in their health with thousands of products, nearly half of which are HSA/FSA eligible.

We're a small, fast-moving team of less than 10 with plans to grow to ~20 over the next two years. We're in an intense growth stage where everyone owns their domain, collaborates across functions, and operates with high velocity. If you want to be early at a company with real traction, real revenue, and a product people genuinely love, this is that opportunity.

You'll own two core areas of the business: our shop marketplace operations (65%) and end-user support (35%). This is a hands-on role where you'll manage the day-to-day health of our product catalog, be the voice customers hear when they need help, and work closely with our product team to optimize our product and customer experience.

• Manage and optimize our shop marketplace of health and wellness products
• Upload and review new product listings daily
• Maintain strong data management across the catalog to ensure clean, accurate product data
• Create and curate collections based on health and wellness trends, seasonal themes, and user interests
• Proactively research and recommend new brands and products to incorporate into the marketplace
• Contribute to and refine our curation standards

• Serve as the frontline for end-user communications, answering daily support tickets through Intercom
• Help users troubleshoot issues and resolve bugs
• Train and maintain our Intercom support bot based on new features, product updates, and common issues
• Surface bugs and user-reported issues to the product team with clear context, and create Linear tickets to get them resolved
• Write and update help articles for new features and product releases
• Maintain our help center library
• Assist the account management team with technical support questions from clients and customers
• Monitor and respond to app store reviews and other avenues of customer feedback

In your first 90 days, you'll know the solutions to nearly every support issue in the queue, you’re publishing 30+ products per day, writing help articles on our latest feature releases, and have trained our support bot on new features and troubleshooting flows.

Intercom · Linear · Webflow · Claude · FigJam · Internal marketplace operations tools

This role has a clear path into a larger marketplace operations position — managing partnerships with key merchants, automating more of our marketplace workflows, and working closely with our product team to shape the future of the shop.

• Have 1–5 years of experience in customer support, marketplace operations, e-commerce, or a related field
• Are organized, detail-oriented, and take pride in clean data
• Communicate clearly and confidently across functions — you're comfortable flagging issues, sharing context, and asking questions
• Genuinely put the customer first
• Are comfortable in a fast-moving environment where priorities shift and flexibility is essential
• Are willing to roll up your sleeves and take on tasks outside your immediate role when needed
• Have a love for health and fitness at any level — our team ranges from aspiring couch potatoes to former D1 athletes
• Have experience with Intercom, Linear, or similar support and project management tools (a plus, not a requirement)

• Health insurance options
• HSA/FSA health spending account
• Unlimited PTO
• Downtown Chicago office