Technical Connectivity Specialist

Details

Who We Are

About Stripe

Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world's largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Stripe's mission is to increase the GDP of the internet.

About the Team

Stripe Terminal helps users extend their online presence to the physical world. The Terminal team's mission is to make it easy for businesses to accept in-person payments through use cases such as retail experiences, pop-up stores, and mobile points of sale.

Responsibilities

• Own complex connectivity investigations end-to-end across merchant networks, Wi-Fi, LAN, LTE/5G, ISPs, routers, firewalls, VPNs, Stripe Terminal hardware, SDKs, cloud-based device management, and third-party connectivity partners. Lead technical troubleshooting until the root cause is identified and a sustainable resolution is delivered.
• Partner with Product, Engineering, Technical Support, Product Support Operations, Solutions Architecture, Sales, and third-party connectivity providers to coordinate incidents, align stakeholders, remove blockers, and drive improvements.
• Create runbooks, troubleshooting guides, AI-assisted diagnostics, dashboards, support processes, documentation, and enablement materials to improve support effectiveness.
• Act as Stripe's connectivity expert for complex Terminal users, working directly with enterprise customers, SaaS platforms, IT teams, and external partners across email, chat, and live support engagements.
• Identify recurring user pain points and systemic issues through support trends, diagnostics, and field insights. Translate these findings into product improvements, engineering priorities, preventative actions, partner service enhancements, support tooling, documentation, and scalable operational solutions.

Requirements

Minimum Requirements

• 5+ years of experience troubleshooting complex connectivity issues across enterprise environments.
• Deep knowledge of TCP/IP, DNS, DHCP, NAT, VPNs, routing, switching, Wi-Fi (802.11), LTE/5G, firewalls, MDM, and network diagnostic tools such as Wireshark, packet captures, traceroute, and nmap.
• Ability to troubleshoot across the full technology stack, including networks, infrastructure, devices, operating systems, firmware, and applications, using logs, diagnostics, and observability platforms such as Splunk, Datadog, Grafana, and Logscale.
• Strong customer-facing technical advisory skills, including the ability to work with enterprise IT teams, merchants, and executives and explain complex technical concepts clearly.
• Ability to collaborate across Support, Product, Engineering, Solutions Architecture, Sales, and external connectivity partners.
• Strong analytical skills, including SQL and data analysis, and experience creating scalable processes, playbooks, and documentation.

Preferred Qualifications

• Experience supporting payment hardware, POS systems, and in-person payment solutions, including card readers and device management.
• Familiarity with REST APIs, Terminal SDKs, and the Android networking stack.
• Experience building internal tools, dashboards, or AI-assisted diagnostics for support operations and troubleshooting.
• Willingness to travel for customer site visits, pilot deployments, and complex escalations when required.