Technical Support Engineer, L1/L2 at Twingate

Twingate is building a modern remote access solution that simplifies and improves the way businesses secure access to their cloud, SaaS, and on-prem resources. Twingate is backed by leading investors such as BOND, WndrCo, 8VC, Green Bay Ventures, SignalFire, and Dropbox founders Drew Houston and Arash Ferdowsi. Our investors share our belief that in a world where workforces are becoming increasingly distributed, it is critical to be able to effectively secure access to apps, data, and environments. As part of our company culture, our belief in putting the customer first permeates our thinking in everything from our customer communications to the design process behind the product itself. If you take pride in creating experiences with the customer firmly at the center of the picture, we'd love to work with you. Responsibilities • Serve as the primary point of contact for inbound support requests via email, portal, and Slack (for customers who engage us that way), triaging and routing issues to the right teams. • Diagnose and troubleshoot technical issues across Twingate deployments spanning Windows, macOS, Linux, iOS, and Android clients, as well as Connectors deployed in cloud, on-prem, container, and Kubernetes environments. • Work through problems spanning networking (DNS, routing, NAT, firewalls), identity (Okta, Google Workspace, Entra ID / Azure AD, JumpCloud), and endpoint platforms — analyzing client and connector logs, packet captures, and configuration to find root cause. • Reproduce customer issues in-house where needed to confirm behavior and accelerate resolution. • Collaborate with senior Technical Support Engineers on complex or sensitive cases, and escalate product or infrastructure issues to Engineering with clear reproduction steps, logs, and impact summaries. • Document findings, fixes, and known issues in our knowledge base and internal runbooks — and continually improve them. • Represent the voice of the customer by providing structured feedback to Product, Engineering, and Docs teams to improve the overall customer experience. • Partner with other customer-facing teams (Customer Success, Sales Engineering) on accounts that need coordinated support. Qualifications • 1–3 years in a technical support, IT, or help desk role, ideally supporting infrastructure, networking, or security products. • Solid foundation in TCP/IP networking (DNS, routing, NAT, firewalls) and a working understanding of VPN, ZTNA, or similar remote access technologies. • Comfortable troubleshooting across macOS, Windows, and Linux — reading logs, tailing processes, and using standard CLI tools to narrow down an issue. • Exposure to modern SaaS tools, at least one major cloud platform (AWS, GCP, or Azure), and common identity providers (Okta, Google Workspace, Entra ID). • Strong written and verbal communication — you can explain technical concepts clearly and patiently, and you write tickets and docs that teammates genuinely want to read. • Customer-obsessed: you take ownership of a problem, communicate proactively, and treat every interaction as an opportunity to build trust. • Organised, curious, and eager to grow — you're not afraid to say "I don't know, but I'll find out." • Comfortable working in a fully remote environment with teammates across time zones. Desired Skills • Prior experience supporting remote access or security tools (VPN, ZTNA, SASE, ZTA). • Scripting knowledge (Bash, PowerShell, or Python) to accelerate troubleshooting and automate repetitive tasks. • Hands-on with packet captures and analysis tools (Wireshark, tcpdump) and general network debugging. • Familiarity with containerized and orchestrated environments (Docker, Kubernetes). • Experience with modern support tooling (we use Pylon for ticketing and customer engagement, and Slack as our primary internal and customer collaboration channel; prior experience with Pylon, Zendesk, FreshDesk, Teams, or similar is a plus). • Comfortable interacting with technical end users, IT admins, and non-technical stakeholders alike. Not sure if you tick every box? That's okay. At Twingate, we care more about your potential, your perspective, and your enthusiasm for what we're building than a perfect checklist match. We believe the best teams are made up of people from all kinds of backgrounds, with different experiences and ways of thinking. So if you're excited about our mission to provide exceptional customer experiences and make secure access simple, but you're unsure if you're the exact fit — reach out anyway. We're here to solve big problems together, and great ideas can come from anywhere. Benefits & Perks • Virtual-first working model coupled with in-person events • Medical (PPO, HMO, HDHP), dental and vision insurance — employees covered 100% • Basic Life, AD&D and disability insurance • Flexible Spending Accounts • Healthcare, Dependent Care and Commuter Health Savings Accounts • Flexible Paid Time Off • Paid Holidays, Sick Leave (10 days), Paid Parental Leave (6 weeks), Maternity Leave (12 weeks FMLA) • Retirement plan • Wellness — family and parenting support, remote physical therapy, mental health support, and more • Equity What We Value • High Agency: We own the problem and don't think in silos. "Not my job" is not an acceptable excuse if something is not working. Figure out what's wrong and take initiative to solve the problem. Speak up. Company success is everyone's job. • Deliver Customer Value: Company success follows customer success (not the other way around). Everything we do starts and ends with delivering value to our customers. • Continuous Improvement: Making small improvements consistently is preferred to aiming for big leaps. We embrace that we may not get it right the first time, so we learn by doing, making mistakes, and course correcting constantly. 1% better every day is how we accomplish great things over time. • Go Find Out: We seek a deeper understanding beyond the surface, and get our hands dirty with ground truth data (no matter the seniority). We know anecdotes can be more powerful than aggregate stats because they can reveal hidden truths. Always be learning. • Startup DNA: We operate at a higher clock speed and believe small committed teams can make the impossible possible. We embrace that great results only come with great effort, and we lift each other to achieve more than we could achieve alone. Twingate embraces diversity. We are proud to be an equal opportunity workplace and do not discriminate on the basis of sex, race, color, age, pregnancy, sexual orientation, gender identity or expression, religion, national origin, ancestry, citizenship, marital status, military or veteran status, genetic information, disability status, or any other characteristic protected by federal, provincial, state, or local law. Twingate is committed to working with and providing reasonable accommodation to individuals with disabilities. If you would like to request a reasonable accommodation for a medical condition or disability during any part of the application process, please contact: [Upgrade to PRO to see contact]