Technical Connectivity Specialist

Stripe; Toronto; On-site; CAD 120,000 - 150,000; Full time

Benefits offered by this job

Equity

Bonuses/Success incentives

Medical benefits

Wellness stipends

Job summary

Stripe is seeking a connectivity expert to own end-to-end investigations across enterprise networks for Stripe Terminal. You will troubleshoot across Wi‑Fi, LAN, VPNs, and device management, coordinating with Product, Engineering, and Sales to drive improvements.

You will act as a trusted advisor to enterprise customers, providing technical guidance and building scalable support processes, dashboards and runbooks to empower the global team as Terminal scales.

Qualifications

• 5+ years of enterprise networking and connectivity troubleshooting experience.
• Strong knowledge of TCP/IP, DNS, DHCP, NAT, VPNs, routing, and Wi‑Fi.
• Experience with logs/observability tools (Splunk, Datadog, Grafana, Logscale).

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, leading technical troubleshooting until root cause identified.
• Coordinate incidents with Product, Engineering, Support and Sales to align stakeholders and drive improvements that enhance Stripe Terminal support.
• Create runbooks, troubleshooting guides, dashboards and enablement material to improve support effectiveness.
• Act as Stripe's connectivity expert with enterprise customers, IT teams and external partners to troubleshoot complex issues across email, chat and live support.
• Translate support trends into product and operational improvements for Stripe Terminal scalability.

Skills

Networking expertise

Connectivity troubleshooting

SQL & data analysis

Customer-facing advisory

Cross-functional collaboration

Tools

Wireshark

Datadog

Grafana

Splunk

Logscale

Traceroute

nmap

Job description

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. 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.

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. 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.

About The Team

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.

What you'll do

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, 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.

Who you are

Minimum Requirements

• 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.

Preferred Qualifications

• 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.

In‑office expectations

Office‑assigned Stripes in most of our locations are currently expected to spend at least 50% of the time in a given month in their local office or with users. This expectation may vary depending on role, team and location. For example, Stripes in Stripe Delivery Center roles in Mexico City, Mexico, Bengaluru, India, and Dublin, Ireland work 100% from the office. Also, some teams have greater in‑office attendance requirements, to appropriately support our users and workflows, which the hiring manager will discuss. This approach helps strike a balance between bringing people together for in‑person collaboration and learning from each other, while supporting flexibility when possible.

Pay and benefits

The annual US base salary range for this role is $124,600 - $186,800. For sales roles, the range provided is the role’s On Target Earnings ("OTE") range, meaning that the range includes both the sales commissions/sales bonuses target and annual base salary for the role. This salary range may be inclusive of several career levels at Stripe and will be narrowed during the interview process based on a number of factors, including the candidate’s experience, qualifications, and location. Applicants interested in this role and who are not located in the US may request the annual salary range for their location during the interview process.

Additional benefits for this role may include: equity, company bonus or sales commissions/bonuses; 401(k) plan; medical, dental, and vision benefits; and wellness stipends.

We look forward to hearing from you.

At Stripe, we're looking for people with passion, grit, and integrity. You're encouraged to apply even if your experience doesn't precisely match the job description. Your skills and passion will stand out—and set you apart—especially if your career has taken some extraordinary twists and turns. At Stripe, we welcome diverse perspectives and people who think rigorously and aren't afraid to challenge assumptions. Join us.