Executive Assistant

About The Bloomwell Collective

Bloomwell Collective is a founder-led consulting, advisory and investment firm. We advise ambitious founders and leadership teams, invest in search funds and acquisition entrepreneurs, and bring proven operating experience to businesses ready to grow.

The role

We are hiring a part-time Executive Assistant to support both founders. You will keep two busy calendars, inboxes and sets of priorities running smoothly, and you will spot problems before they reach either founder. This role is part-time by design, with a mix of in-person and remote hours each week.

What you will do

• Manage two complex calendars, resolving conflicts and protecting time for priority work
• Triage both inboxes and draft replies in each founder’s voice
• Prepare for meetings with agendas, briefing notes and materials
• Coordinate with clients, investors, advisors and vendors on the founders’ behalf
• Draft and proofread business communications, proposals and presentations
• Track projects and deadlines across the business and follow up on what is outstanding
• Handle administrative tasks such as expenses, invoices, filing and subscriptions
• Support new business projects with research and coordination
• Handle confidential business and personal matters with complete discretion

What you bring

• 2 or more years supporting senior leaders, ideally two or more at once
• Excellent written English and the ability to write in someone else’s voice
• Sound judgment and discretion with confidential matters
• Calm prioritizing when two leaders need different things at the same time
• Fluency with Google Workspace, Zoom, Docusign and comfort using AI tools
• A home base in Toronto and the ability to be in person on set days

Nice to have

• Experience supporting founders, investors or a family office
• Light bookkeeping, expenses and invoicing
• Brand, social media or basic design skills

What success looks like

• In 30 days: you run calendars and inboxes, and you know the key clients, investors and advisors by name.
• In 90 days: you anticipate rather than react and you own projects from start to finish and have improved how the office runs.

Hours: 20 per week, Monday to Friday. There is no fixed daily schedule; hours are flexible and agreed week to week.

Location: Hybrid, with up to two in-person days each week and the remaining hours remote.

Start Date: Flexible, mid November.

How to apply

Apply through Indeed with your resume and a cover letter telling us about your experience and why you would be a good fit for this role. Applications are reviewed as they arrive. The Bloomwell Collective welcomes applicants of all backgrounds. Accommodation is available on request at any stage of the hiring process.

Pay: $28.00-$31.00 per hour

Benefits:

• Flexible schedule
• Work from home

Application question(s):

• Are you able to reliably commute to downtown Toronto up to twice a week?

Work Location: Hybrid remote in Toronto, ON