Connectivity Jobs in Chicago, IL (NOW HIRING)

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. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career.

Stripe Terminal helps our users extend their online presence to the physical world. The Terminal team's mission is to make it as easy for businesses to accept in-person payments as the Stripe API has done for online payments. With Terminal, businesses can unlock in-person payment use cases that are right for their business model, whether it's creating a superb retail experience, extending their website to a pop-up store, or enabling a mobile point-of-sale at their next event.

• 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, leading technical troubleshooting until the true root cause is identified and a sustainable resolution is delivered.
• Partner cross-functionally with Product, Engineering, Technical Support, Product Support Operations, Solutions Architecture, Sales and third-party connectivity providers to coordinate complex incidents, align stakeholders, remove blockers and drive product, engineering or partner improvements that enhance the Stripe Terminal support experience.
• Drive operational excellence by creating runbooks, troubleshooting guides, AI-assisted diagnostics, dashboards, support processes, documentation and enablement material that empower the wider Support organization to resolve issues independently and continuously improve support effectiveness.
• Act as Stripe's connectivity expert for the largest and most complex Terminal users, working directly with enterprise customers, SaaS platforms, IT teams and external partners to troubleshoot complex connectivity and hardware issues, provide technical guidance and build user confidence across email, chat and live support engagements.
• Be the voice of the user and drive the continuous improvement of Stripe Terminal's connectivity capability by identifying recurring user pain points and systemic issues through support trends, diagnostics and field insights. Translate these learnings into product improvements, engineering priorities, preventative actions, partner service enhancements, support tooling, documentation and scalable operational solutions that improve reliability and technical excellence as Terminal scales globally.

• A deep networking expert with 5+ years of experience troubleshooting complex connectivity issues across enterprise environments, with strong 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.
• An exceptional technical investigator who can troubleshoot across the full technology stack, from network and infrastructure to devices, operating systems, firmware and applications, using logs, diagnostics and observability platforms (e.g. Splunk, Datadog, Grafana, Logscale) to identify root causes and drive issues to resolution.
• A trusted customer-facing technical advisor who partners confidently with enterprise IT teams, merchants and executives, translating complex technical concepts into clear guidance while helping customers implement best-practice network configurations and environments.
• A cross-functional systems thinker who thrives in ambiguity, collaborates effectively across Support, Product, Engineering, Solutions Architecture, Sales and external connectivity partners, and uses data to identify recurring issues and influence product and operational improvements.
• An operational builder who combines strong analytical skills (including SQL and data analysis) with a continuous improvement mindset, creating scalable processes, playbooks and documentation that increase team capability and improve the customer experience.

• Experience supporting payment hardware, POS systems and in-person payment solutions, including hands-on experience with 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 to improve support operations and troubleshooting.

Willingness to travel for customer site visits, pilot deployments and complex escalations when required.