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 escalate. 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 robust 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 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

Being upfront so you self-select:

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 career development budget

In-studio, Toronto — this is not a remote role How to Apply

Send an email to [email protected] with the subject line Chief of Staff — [Your Name] and include:

A short note (250 words max) on why this role, why now

One example of a system or process you built that meaningfully improved a business

One example of a hard conversation you had to have at work — and how it landed

Your resume or LinkedIn

Please do not attach a portfolio. This isn't a creative role.

Shortlisted candidates will complete a 30-minute intro call, followed by a paid mini-project (2 hours, compensated) that mirrors real work you'd do here.

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.

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