Operations & Executive Assistant

Feathery automates data intake workflows for insurance and wealth management firms. Industry leaders rely on Feathery to power mission-critical workflows like underwriting, client onboarding, and automated account openings.

With rapid revenue growth and expanding enterprise demand, we’re scaling our internal operations to support a fast-growing team and increasingly complex go-to-market efforts.

As Feathery grows, we need strong operational support to keep the company running smoothly — from executive coordination to office operations and go-to-market team logistics.

We’re hiring an Operations & Executive Assistant to serve as a central hub for coordination across leadership and GTM teams. This role is ideal for someone who is highly organized, detail-oriented, and enjoys keeping teams aligned and operating efficiently in a fast-paced environment.

You’ll work closely with executives and cross-functional teams to ensure day-to-day operations run seamlessly.

This is a high-ownership role that blends:

• Executive support and calendar management

• Office operations and workplace coordination

• GTM team logistics and event coordination

• Cross-functional operational support

You’ll play a key role in enabling leadership and GTM teams to operate effectively by handling the details that keep everything moving.

• Manage calendars, scheduling, and meeting coordination for executives

• Coordinate internal and external meetings, including preparation of materials and follow-ups

• Handle travel planning, logistics, and expense management

• Support executive priorities and special projects as needed

• Oversee day-to-day office operations and ensure a smooth workplace experience

• Manage vendors, supplies, and office logistics

• Coordinate team offsites, on-sites, and internal events

• Help maintain a productive, organized, and welcoming work environment

• Support sales and go-to-market teams with scheduling, logistics, and coordination

• Assist with planning and execution of conferences, customer events, and field activities

• Coordinate cross-functional meetings and ensure alignment across teams

• Help track key initiatives and follow up on action items

• Improve internal processes to increase efficiency and reduce friction

• Maintain internal documentation and operational systems

• Support onboarding logistics for new hires

• Assist with ad hoc operational and administrative needs across the company

• 1–3+ years of experience in executive support, operations, or administrative roles

• Highly organized with strong attention to detail and follow-through

• Excellent communication skills and ability to coordinate across teams

• Strong time management skills and ability to prioritize in a fast-paced environment

• Proactive, resourceful, and comfortable handling ambiguity

• Experience supporting executives and/or go-to-market teams

• Comfortable working in a high-growth startup environment

• Experience supporting sales or go-to-market teams

• Experience coordinating events, conferences, or offsites

• Familiarity with tools like Google Workspace, Slack, Notion, and CRM systems

• Experience in a high-growth B2B SaaS company

• Competitive compensation and equity

• Health, dental, and vision coverage

• Unlimited PTO

• Downtown Toronto office location

• Office snacks and lunches

• A supportive, low-ego team that values ownership and growth

• Company offsite to connect and recharge

Feathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.