Operations & Executive Assistant

About the company

Feathery builds automation tools for data intake workflows used by insurance and wealth management businesses. Its platform supports essential processes such as underwriting, client onboarding, and automated account openings.

With strong revenue momentum and growing enterprise demand, the company is expanding its internal operations to support a larger team and more complex go-to-market activities.

Why this role exists

Feathery is looking for an Operations & Executive Assistant to provide dependable coordination across leadership, office operations, and go-to-market teams. This position is well suited to someone who is highly organized, meticulous, and energized by helping teams stay aligned in a fast-moving environment.

The role sits at the center of day-to-day execution and works closely with executives and cross-functional partners to keep operations running smoothly.

Role overview

This is a broad, high-responsibility position that combines executive assistance, workplace operations, GTM coordination, and general cross-functional support. The person in this role will handle the details that keep leadership and commercial teams moving efficiently.

Key responsibilities

• Support executives by managing calendars, scheduling, and meeting coordination.
• Arrange internal and external meetings, including prep materials and follow-up tasks.
• Organize travel, related logistics, and expense tracking.
• Assist with executive priorities and special initiatives as needed.
• Oversee everyday office operations and contribute to a smooth workplace experience.
• Coordinate vendors, office supplies, and general workplace logistics.
• Plan and support team offsites, on-sites, and internal company events.
• Help maintain an efficient, organized, and welcoming office environment.
• Assist sales and go-to-market teams with scheduling and coordination needs.
• Support planning and execution for conferences, customer events, and field activities.
• Coordinate cross-functional meetings and help keep teams aligned.
• Track initiatives and follow up on outstanding action items.
• Improve internal processes to reduce friction and improve efficiency.
• Maintain documentation and operational systems used internally.
• Assist with onboarding logistics for new employees.
• Handle additional administrative and operational tasks across the business as needed.

Candidate profile

The ideal candidate has 1–3+ years of experience in executive support, administration, or operations. They bring excellent organization, strong attention to detail, and dependable follow-through.

This person should communicate clearly across teams, manage time well, prioritize effectively, and stay calm when working through ambiguity. Experience supporting executives or go-to-market teams is especially relevant, as is comfort in a high-growth startup setting.

Preferred experience

Additional value will come from experience supporting sales or go-to-market functions, coordinating events or offsites, working with tools such as Google Workspace, Slack, Notion, and CRM platforms, or contributing in a high-growth B2B SaaS environment.

What the company offers

• Competitive pay along with equity participation.
• Health, dental, and vision insurance coverage.
• Unlimited paid time off.
• A downtown Toronto office location.
• Snacks and lunches provided in the office.
• A supportive, low-ego team culture focused on ownership and development.
• Company offsites designed for connection and rest.

Equal opportunity statement

Feathery is an equal opportunity employer and makes hiring decisions without regard to race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other protected characteristic. Reasonable accommodations are available on request.