Who you are

- 5+ years in Technical Support, Solutions Engineering, Technical Account Management, or Technical Project Management — with at least some of it in a senior or lead capacity

- Experience owning customer-facing incident or maintenance communication. You will be writing status page updates, incident notices, and escalation emails. You understand the difference between transparency and alarm

- Robust internal communication skills. You will be the translation layer between customers, VGS account management, and VGS product and engineering. You should be able to operate in different contexts and understand how to translate between the technical, operations, and business contexts of conversations to ensure context is not lost between stakeholders

- Autonomy. You are comfortable deciding and then reporting, rather than checking first. You'll have a few hours of overlap with your manager each day and spend the rest of your shift as the main decision-maker

- Strong command of HTTP, REST APIs, and proxies

- Independent network debugging — DNS, TCP/IP, routing, connectivity, TLS/SSL handshakes. Be ready to describe a specific problem you diagnosed and how you narrowed it down

- English at C1 or above, written and spoken. You'll be writing text that customers and executives read, under time pressure

- Willingness to work PT business hours on a sustained basis

- Experience with tokenization, payment processing, cryptology, or security products

- BA/BS degree
- A knack for out-of-the-box thinking that thrives in a fast-paced startup environment

- Reading and debugging code in at least one of Python, Go, Java, or a similar language. You won't ship production code

- We're looking for passionate professionals who take pride in their craft and want to help grow a team tackling some of the most critical problems in payments. People who thrive here are curious by nature, unafraid of hard problems, and motivated by the chance to build something that matters at scale

- If you're driven to make a meaningful impact,



work at the leading edge of payment technology, and grow your career alongside a team that values ownership, collaboration, and continuous learning, you'll feel right at home at VGS

What the job involves

- The majority of this role is hands-on technical work: debugging, troubleshooting network and integration issues, onboarding new customers, and resolving tickets
- The remainder is operational ownership and cross-team coordination. The support team plays a vital role in translating between our Engineering and Go-To-Market teams (including account management and sales)

- During incidents, outages, escalations, and planned maintenance, you are the primary on-shift decision-maker for PT business hours: you decide whether an incident goes on the public status page, approve the wording of customer notifications, set maintenance timing, and coordinate as needed with the GTM teams so that they are aware of any impacts to their clients. These decisions sit with leadership today, and we want them to be owned within Support

- They come up infrequently but are time-sensitive and customer-visible. You'll have a written scope of what you can approve independently and what requires the manager, expanding as you establish a track record

- Serve as the senior decision-maker for the Support team during PT business hours. Escalations, judgment calls, and approvals land with you. You're the person on shift with the standing to decide, not to route

- Own incident and maintenance communications. Assess severity and customer impact, decide when to post to the public status page, write or approve the wording, including team drafts, and keep it up to date through resolution





- Set and coordinate maintenance timing. Choose windows based on real customer traffic patterns and regional load, negotiate them with engineering, inform internal client-facing teams about and make sure the notice goes out with enough lead time for customers to plan

- Coordinate multi-team projects where Support is a stakeholder: migrations, deprecations, launches, and customer-specific rollouts. Track dependencies and keep the parties honest about status

- Debug deeply. Reproduce issues with cURL and Postman, read logs, and trace requests across VGS infrastructure, customer systems, and downstream gateways.

Diagnose network problems independently: DNS, TCP/IP, routing, timeouts, connection resets, and TLS/SSL handshake failures

- Resolve an issue, find a workaround, or escalate with a bug report good enough for engineering to act on immediately

- Drive mid-tier and long tail customer integrations from kickoff to go-live, coordinating between customer engineers and internal teams

- Write up nontrivial investigations as internal runbooks or public documentation

- Prepare and deliver customer training, building the material where it doesn't exist

- Meet SLA and quality targets, and help the team meet theirs

- Participate in the weekend on-call rotation (every 3rd weekend, Saturday and Sunday, 8:00–20:00 PT). On-call is monitoring coverage, not a full working day — you respond to urgent incidents and time-sensitive requests, while routine tickets wait for the next business day

Benefits

- Competitive health benefits including medical, dental, & vision insurance

- VGS stock options
- 401k plan, with employer matching 4% and immediate vesting of employer match

- Life & disability insurance

- Pre-tax flexible spending accounts (dependent and healthcare FSA)

- Flexible work hours and flexible PTO

- 11 US company holidays

- Eligibility for health benefits starts on Day 1!

- New hire home office set up allowance

- Professional learning reimbursement

📌 Technical Support Engineer (Canada)
🏢 Very Good Security
📍 Canada