We're Two Whimsical Florists — a custom artificial floral studio in Toronto designing weddings across Canada, the U.S., and beyond. We're a small team building something ambitious: a wedding studio that couples actually trust — transparent pricing, custom rentals, no gatekeeping.
We're growing. We need someone who can build the operational spine that lets us grow well.
About Us We're Two Whimsical Florists — a custom artificial floral studio in Toronto designing weddings across Canada, the U.S., and beyond. We're a small team building something ambitious: a wedding studio that couples actually trust — transparent pricing, custom rentals, no gatekeeping.
We're growing. We need someone who can build the operational spine that lets us grow well.
The Role We're hiring a Chief of Staff / Operations Lead to become the operational and strategic right hand to the founders.
This is a hybrid role combining studio operations, team leadership, founder support, relationship-building, and creative problem-solving. You will ensure the day-to-day business runs smoothly while helping the founders stay focused, organized, and accountable to the company's larger priorities.
You'll build and enforce systems, oversee production and logistics, lead internal conversations, and identify solutions before problems escalated. You'll also represent Two Whimsical Florists in conversations with vendors, collaborators, clients, and community partners.
We need someone who can learn how the founders think and communicate, adapt to our voice, and confidently act on our behalf when appropriate. At the same time — we don't want someone who simply agrees with us. You must be comfortable pushing back, redirecting our attention, and telling us when something isn't working.
This role requires someone who moves comfortably between detailed execution and higher-level thinking. One moment, you're reviewing the week's production schedule. The next, you're leading a vendor conversation, improving a process, shaping a new offering, or making sure the founders follow through on an important commitment.




You'll be trusted to make decisions, solve problems, and move work forward without requesting permission at every step.
What You'll Own Studio Operations Weekly production planning, order pipeline, delivery logistics
Studio scheduling, rental turnovers, workshop logistics
Vendor and supplier relationships
Inventory systems and materials management
Team Accountability Weekly team huddles and accountability check-ins
Enforcement of SOPs and standards across production, packing, and design
Support the founders in 1:1s and performance conversations
Escalate people issues early — before they become problems
Founder Support Manage the founders' calendars, meeting prep, and follow-through
Filter what needs their attention vs. what you can handle directly
Draft communications, close open loops, track their commitments
Represent the company consistently in conversations when they're not in the room
Systems + Growth Own the day-to-day of HoneyBook, Notion, Shopify, and Google Workspace
Track weekly KPIs and flag issues before they compound
Support the launch of new offerings (Storytelling tier, workshops, community events)
Identify inefficiencies and propose fixes without waiting to be asked
Creative + External Presence (bonus) A strong creative eye is a plus — helpful on styled shoots, in office setup during peak weekends, and content moments
Comfort representing the brand externally in vendor and partner conversations
You don't need to be a designer, but taste-level judgment helps
Who You Are Exceptionally organized. You naturally create order in fast-moving environments.
Logistics-oriented — you anticipate what could go wrong before it happens




You take ownership and make thoughtful decisions without needing constant approval
Comfortable enforcing systems, standards, deadlines, and accountability
You communicate confidently with employees, vendors, clients, and collaborators
Warm and relationship-oriented, but direct when a hard conversation is needed
You can adapt to the founders' voice and represent the company consistently
You are comfortable challenging the founders, redirecting priorities, and holding them accountable
Resourceful and solutions-focused — you adapt when plans change
Strong creative instincts and good judgment around aesthetics and brand presentation
You enjoy strategic thinking and hands-on execution equally
Energized by helping a growing company become more organized, professional, and scalable
Experience in wedding planning, event production, hospitality, venue operations, creative agencies, or another fast-paced service business is strongly preferred.
3+ years in operations, project management, chief of staff, or senior executive assistant roles.
What This Role Is Not Not a creative role. Creative eye is a bonus, but you're not designing florals or making content.
Not passive. You're not executing on someone else's plan — you're building the plan.
Not "get back to me" energy. You're proactive, decisive, and take ownership without needing permission.
Not for someone who needs constant affirmation. Your work is the evidence.
If any of those made you flinch, this isn't your role. And that's okay.
Compensation Base: $65,000 – $75,000 CAD, based on experience
Performance bonuses tied to team and operational milestones
Paid time off, sick days, and a modest professional development budget
In-studio, Toronto — this is not a remote role
Applications open until we find the right person.
Two Whimsical Florists is committed to building a team that reflects a range of backgrounds and perspectives. We encourage applications from BIPOC candidates, women, LGBTQ+ candidates, immigrants, and people with disabilities.

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📌 CHIEF OF STAFF / OPERATIONS LEAD (Ontario)
🏢 Two Whimsical Florists
📍 Ontario