Senior Technical Support Lead

Who We Are:

Stay Ai is powered by savvy DTC industry vets, who have each been building subscription programs for over ten years. We’ve worked with over 300+ subscription-focused CPG brands that have generated hundreds of millions in subscription revenue alone. Our product is shaped by lifelong marketers who specialize in acquisition and retention, not developers—and it shows.

We have amazing investors like Telescope Partners, with participation from Boulder Food Group, Riverpark Ventures, and Vanterra Capital. Previous investments were led by Watchfire Ventures, alongside industry leaders such as Nik Sharma (Sharma Brands) and Adam Turner (Postscript).

We are not afraid of challenging work and are excited to build the next big thing. Sound good to you? Then, please read more about our role!

Our Culture:

We are dedicated to our work, but equally committed to celebrating our achievements. Collaboration is at the heart of everything we do, as we firmly believe in the power of teamwork. While we are remote-first as a company, we try to create opportunities to meet each other. That's why we organize annual offsite retreats in beautiful Park City and Mexico!

Who You Are:

As senior technical support lead you will own the day to day operations of technical support and provide technical support to our strategic merchants. You will work with our Customer Success team to assist with technical issues, triage with our product and engineering teams, and collaborate with our sales engineers on implementation of custom work.

Key Responsibilities

• Serve as the highest-tier technical escalation point for complex, cross-system, and high-impact customer issues.

• Diagnose and resolve issues involving APIs, integrations, webhooks, data pipelines, authentication, and platform configuration.

• Perform deep technical investigations using logs, monitoring tools, databases, and internal debugging environments.

• Lead the technical response during major incidents, coordinating with Engineering, Product, and Support stakeholders.

• Drive root-cause analysis and post-incident reviews, documenting findings and ensuring preventive actions are implemented.

• Maintain ownership of long-running or multi-team technical issues until full resolution.

• Develop, refine, and enforce best practices for troubleshooting, escalation, and customer communication.

• Identify recurring product issues or operational gaps and proactively propose solutions.

• Contribute to internal runbooks, knowledge base articles, and tooling improvements to streamline support workflows.

• Act as a bridge between Support and Engineering/Product teams, translating customer issues into actionable technical insights.

• Provide feedback on product reliability, edge-case behaviors, and customer experience pain points.

• Participate in technical reviews for new features to ensure support readiness and identify potential risk areas.

• Manage high-stakes customer interactions that require deep technical understanding and clear communication.

• Assist customers with advanced debugging, configuration best practices, API usage, and integration flows.

• Represent the customer perspective during internal discussions around product stability, enhancements, and roadmap needs.

What You'll Bring:

• 5–7+ years of experience in technical support, technical operations, or product support roles in a SaaS or cloud environment.

• Expert troubleshooting skills across Shopify solutions with a focus on subscriptions

• Ability to break down complex technical problems and communicate findings clearly to both technical and non-technical audiences.

• Experience working directly with engineering teams on bug triage, debugging, and release readiness.

Nice-to-Haves

• Strong familiarity with tools such as Postman, cURL, SQL, logging/monitoring systems, and debugging utilities.

• Familiarity with incident management frameworks (e.g., ITIL, post-mortems, RCA methodology).

• Background supporting products with APIs, integrations, or data pipelines.

• Prior experience in a customer-facing senior escalation or technical lead role.