Chief Of Staff ​/ Operations Lead

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.

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.

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.

• Weekly production planning, order pipeline, delivery logistics
• Studio scheduling, rental turnovers, workshop logistics
• Vendor and supplier relationships
• Inventory systems and materials management

• 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

• 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

• Own the day-to-day of Honey Book, 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

• A strong creative eye is a plus — helpful on styled shoots, on-site 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

• 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…