Startup jobs in Canada

At Octopus Pod, we help founders find the right hands when the chaos of scaling gets real. We’re partnering with Pluvo—a fast-growing startup reimagining financial planning through human-centred AI. They just closed a fresh round and are moving fast: packed calendars, investor calls, and no margin for error.

We’re helping them find an Executive Assistant who doesn’t just “support” the team - they run the cockpit. You’ll be the glue across leadership, ensuring their days run with clarity and momentum.

This isn’t your average admin role. It’s ideal for someone on the path to Chief of Staff—someone who thrives in fast-moving environments and knows how to anticipate needs before they’re spoken.

This is a hybrid role, primarily based at Pluvo’s Ottawa HQ. You’ll be in the room where decisions happen—and sometimes on the road with execs in places like San Francisco or NYC. Travel-readiness is a must.

Requirements

• Own the calendar, like air traffic control. Keep execs focused by running schedules, flagging conflicts early, and keeping investor calls, demos, and deep work time in perfect sync.
• Keep the playbook running. Prep materials, send follow-ups, track action items—so nothing slips between the cracks.
• Light support for the full exec bench. Beyond the CEO/CFO, you’ll assist the CTO/COO with scheduling and coordination. Travel like a pro. Plan investor trips, offsites, and internal events like a seasoned concierge.
• Maintain HubSpot hygiene. Add contacts, update lead records, and prep execs with the context they need to walk into every meeting with confidence.
• Personal support when needed. Light errands or admin tasks to keep the CEO focused on growth, not groceries.
• Anticipate, communicate, unblock. You’ll flag bottlenecks, surface risks, and make sure nothing falls through the cracks.

• Have 4+ years of experience supporting C-suite leaders (ideally at a startup or VC-backed company).
• Can juggle five things and still catch the sixth before it hits the floor.
• Have a sharp eye for details—typos in invites or misaligned decks don’t stand a chance.
• Can handle strong personalities with calm, confident energy.
• Know your way around Google Workspace, Notion, Monday.com, Jira, and especially HubSpot.
• Are available and responsive—even after hours if needed.
• Have a car and a valid license (some in-person errands required).
• Are thinking three steps ahead and ready to grow into a Chief of Staff.

Benefits

• Competitive compensation
• Full health and dental
• Company-paid travel (flights, hotels, per diems)
• Home office setup stipend
• Quarterly bonus eligibility
• Clear growth path to Chief of Staff