Technical Support Specialist

VendNovation•Redmond, WA

8d•Hybrid

About The Position

VendNovation is seeking a Technical Support Specialist to join their Enterprise Client Team. This role is crucial for managing a fleet of over 2,500 unattended machines, each a Windows PC integrated into expensive hardware, distributed nationwide. The team handles 30-40 tickets daily, originating from machine telemetry and direct communication with the customer's engineers. This is not a call center position; responsibilities include remote diagnosis, troubleshooting hardware and software issues, and communicating during incidents. The role requires a proactive individual who can sort through complex issues, automate recurring tasks, and act as a technical owner for the fleet. The company is 25 years old with approximately 50 employees, offering stability and a bureaucracy-free environment. The position offers regular hours (9:00 AM - 5:00 PM Pacific, Monday-Friday) with no on-call rotation and two days of remote work per week. The specialist will have direct interaction with the customer, acting as a trusted technical advisor.

Requirements

5+ years in technical support, systems support, desktop engineering, field technology, or a related IT role.
Strong hands-on experience with Windows 10 and Windows 11, including services, event logs, device drivers, user accounts, networking, and system configuration.
Proficiency in imaging, configuring, validating, and troubleshooting Windows devices.
Working proficiency with PowerShell (reading, modifying, and writing scripts for operational tasks).
Experience with a remote-access or endpoint-management platform (e.g., LogMeIn Central).
Experience with a ticketing system (e.g., Zendesk), including categorization, prioritization, and note-taking.
Ability to isolate problems across software, hardware, peripherals, and networks, distinguishing symptoms from root causes.
Composure and clarity when communicating with enterprise customers.
Ability to manage a queue with competing demands while maintaining accuracy and follow-through.
Availability to work on-site in Redmond three days a week, 9:00 AM – 5:00 PM Pacific.

Nice To Haves

Experience with unattended devices, kiosks, POS, vending, or other field-deployed systems.
Troubleshooting experience with USB, serial, camera, printer, scanner, or payment peripherals.
Knowledge of TCP/IP, DHCP, DNS, firewalls, VPNs, and cellular connectivity at remote sites.
Experience with Windows event log and crash data analysis.
Experience working with hardware and software vendors or field technicians.
Familiarity with BIOS, firmware, and driver workflows.
Experience writing runbooks and knowledge-base articles.

Responsibilities

Daily triage and resolution of fleet tickets, including Windows issues, application software, drivers, USB and serial peripherals, networking, payment hardware, and cameras.
Prioritize work based on stakeholder needs and communicate status updates.
Perform remote diagnosis using LogMeIn Central, including checking device health, event logs, configurations, restarting services, and confirming recovery.
Write, test, and deploy PowerShell scripts for fleet-wide changes, diagnostics, and data collection, especially during release nights.
Image, configure, test, and prepare Windows systems for deployment, replacement, or repair.
Identify recurring and systemic issues, escalating them with detailed reproduction steps, evidence, and labor cost analysis.
Communicate effectively during incidents, providing information on what happened, actions being taken, workarounds, and resolution status.
Maintain clear case notes and runbooks in Zendesk (transitioning to Salesforce) for knowledge sharing.
Act as a trusted technical voice for the customer, ensuring smooth operations and customer satisfaction.