Support the CEO and a ten-person FileMaker development team by managing work orders, time tracking, IT/security monitoring, onboarding/offboarding, marketing campaigns, and internal documentation. Maintain Hubstaff and FileMaker alignment, administer device security tools, coordinate maintenance/outage communications, and own recurring operational processes to ensure accuracy and reliability.
This is a remote position.
Our client, a specialized team of FileMaker development experts in Vancouver, Canada, is hiring an Executive Assistant & Technical Operations Coordinator to be the CEO's right hand and the operational backbone of a roughly ten-person team.
You will keep our projects, infrastructure, and people running day to day: owning time tracking and work orders, supporting IT and infrastructure, running onboarding and offboarding, handling marketing campaigns, and supporting the CEO directly. You will report to the CEO and work closely with clients, the development lead, and the systems administrator.
This is a broad, detail-critical role, and it is a lot of surface area for the hours - ruthless prioritization, speed, and accuracy matter. The non-negotiables: communications go straight to clients and staff and must be right the first time, and recurring processes have to run without being chased. Strong technical aptitude is essential - you will work in databases, time-tracking and security tools, and basic server / network systems
Employment Type: Ongoing part-time contract
Work Schedule: ~10 hours per week. Mandatory attendance at weekly client status meeting every Wednesday, 11 AM - 12 PM PST
Location: Remote, must work on Pacific Time for time-sensitive work (outage notices, onboarding/offboarding, work-order updates)
What You'll Do:
Operations & Work Orders (core)
- Create, assign, update, complete, and archive work orders in Hubstaff - this is the most frequent recurring task, running roughly one to two work orders a week, each created, assigned, and confirmed back to the requester.
- Keep Hubstaff aligned with the FileMaker NC_Quotes / Time & Billing system.
- Fix assignments, permissions, and time-logging issues for developers; action budget and hours changes accurately.
- Coordinate work-order status and approvals with the development lead, developers, and finance.
IT, Infrastructure & Security
- Run a daily check of the support / hosting queue for emergencies or site-down events; escalate to the systems administrator immediately.
- Track device security compliance across staff (NinjaOne RMM, SentinelOne EDR); administer the 1Password vault.
- Coordinate server maintenance windows and draft and send client outage / maintenance notices; maintain the outage calendar, recipient lists, and the monthly backup-link references.
- Support infrastructure with the systems administrator: backups and backup-failure triage, power, cooling, DNS, firewall / VPN, AWS, hosting tickets, and server-room facilities.
Onboarding & Offboarding
- A few times a year, as the team changes, own onboarding from a standard checklist: accounts, Hubstaff, 1Password, email signatures, and the security / privacy steps.
- Own offboarding from the wiki template: notify each access owner (payroll, systems, HR), track revocation across every system, and confirm completion.
- Coordinate timing and messaging with HR; keep the wiki current.
Marketing & Client Reconnection
- Draft and send newsletters and product updates (EmailOctopus) - low volume, roughly one newsletter a year; track delivery and list health.
- Run webinar invites and reminders (roughly one webinar a quarter); prepare social posts and clips, and handle routine website updates.
- Run reconnection campaigns to former clients; build prospect lists and handle warm follow-ups.
Executive Support
- Manage the CEO's calendar and meetings; send invites and links, send reminders, and follow up on action items on the CEO's behalf - this runs several times a week.
- Support ad hoc research and business projects for the CEO.
- Keep internal documentation organized across Google Drive, the wiki, and Trello.
Requirements
What You'll Bring
- Strong technical aptitude - comfortable with databases (FileMaker an asset), time-tracking / work-order systems, RMM and security tools, and basic server / networking concepts.
- Exceptional attention to detail and accuracy, especially in client email - the right message to the right people, the first time.
- Follows detailed instructions precisely the first time, with little rework.
- Self-directed - anticipates next steps, takes ownership, and works independently.
- Highly organized; juggles many recurring processes without dropping any.
- Discreet and reliable with credentials and confidential information.
- Clear, professional written English; approachable and responsive.
- Comfortable with Hubstaff, Trello, Freshdesk, 1Password, EmailOctopus, Google Workspace, and AI tools (e.g. Claude).
- Executive-assistant or operations experience supporting a founder is a plus.
Security & Compliance (Mandatory)
Our clients are government and utility organizations, so before accessing any client system you must complete a criminal record check and FOIPPA privacy training, and work on a machine running NinjaOne and SentinelOne. You don't need to own one - the team can provide a basic machine (Mac or Windows 11) and recover the cost from pay, or finance the purchase, so it is not on a personal device. These checks and tools are firm requirements.
Success Measures:
- Work orders, budgets, and time tracking are accurate and current.
- Onboarding and offboarding complete on time - no access left open, no gaps.
- Client and maintenance communications go out right, on schedule, to the right people.
- Recurring operations run reliably without being chased.
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