Moniker Executive Retreats - Operations Manager

FULL-TIME | REMOTE Location: Canada Wide** Please note at this time, we are only able to consider candidates who are legally authorized to work in Canada. This includes Canadian citizens, permanent residents, and individuals who already hold a valid work permit. Unfortunately, we are not able to provide visa sponsorship or engage international contractors (including those based in the U.S.A.) for this role. Department: Moniker Executive Retreats Reports to: President & CEO (Sydney Penman & Sean Hoff) Ideal Start Date: August 9th, 2026 (flexible) About the Company: Moniker is an award-winning agency in the Corporate Retreat, Offsite, and Incentive Travel space, with over 13 years of history and 20+ employees across Canada. We are expanding into a new segment of the Corporate Retreat market via a new business line aimed at Executive Retreats. The new brand aims to create meaningful retreat experiences for (i) Executive Teams, (ii) Boards, (iii) Leadership Groups, and (iv) Peer Advisory Forums from communities like YPO, EO, and Vistage. Our goal is to help leaders remove the logistical and planning tasks from the planning process, so they can focus their energy on the elements that will maximize connection, growth, and impact. About the Role: As this will be a new business line within the Moniker umbrella, we are ideally looking for someone who demonstrates a strong "intrapreneurial" potential, having prior experience building out a brand or business from within an established company, and who thrives in both strategy and execution, wearing many hats as the needs and priorities of the business evolve over time. This role will be responsible for managing the complete executive retreat lifecycle from lead intake through post-event wrap-up. The right person must be highly organized, client-focused, and process-oriented to help build the operational engine and SOPs behind our new brand. They love building systems, maintaining order, managing details, and creating exceptional client experiences behind the scenes. They will oversee sales administration, work with property managers, dabble in retreat planning, oversee supplier coordination, sales tracking, website content, CRM management, and platform administration. In short, it’s building a business from the ground up, with the support and resources of a proven business and team behind you. RESPONSIBILITIES: Sales & Client Service • Collaborate with leadership and marketing teams to develop a Go-To-Market (GTM) and client acquisition strategy. • Manage and track the sales pipeline from initial inquiry through signed agreement via our CRM (Pipedrive). • Respond to inbound leads, conduct discovery calls as needed, and follow up on proposals and opportunities. • Serve as the primary client contact throughout the planning process. Property, Supplier & Partnership Relationship Management • Source, evaluate, onboard, and manage a curated portfolio of retreat properties, private villas, and hospitality partners. • Negotiate and enforce property agreements, preferred rates, commissions, concessions, and partnership terms. • Build and maintain a network of trusted suppliers, including transportation providers, private chefs, facilitators, wellness practitioners, activity providers, photographers, and other experience partners for each destination. • Maintain accurate and up-to-date supplier profile information across all systems, databases, and client-facing platforms. • Manage partner contracts, renewals, pricing, insurance requirements, key contacts, and performance reviews. • Continuously inform the future growth of the business through research of new destinations, properties, experiences, and partnership opportunities that enhance the Executive Retreats offering. Retreat Planning & Platform Operations • Support clients through the retreat planning journey using Moniker Executive Retreats' digital tools and planning platform. • Develop retreat proposals, budgets, agendas, timelines, and client-facing planning resources. • Build, manage, and continuously improve the collaborative agenda builder. • Coordinate accommodations, transportation, dining, activities, facilitators, and supplier logistics to ensure retreats are fully prepared for execution. • Prepare retreat documentation, operational plans, and handoff packages, and conduct final quality assurance reviews prior to departure. • Monitor the client's progress throughout the planning process and provide support as needed. Systems, Website & Data Management • Own and maintain operational systems, software platforms, databases, and business tools. • Serve as the internal expert on company technology platforms, including Cockpit, Qwilr, Typeform, and future business systems. • Maintain and update website content, property listings, destination pages, retreat packages, imagery, and marketing assets. • Ensure all digital content, databases, and documentation remain accurate, organized, and aligned with brand standards. • Develop and maintain SOPs, workflows, and operational documentation. • Identify opportunities for automation, process improvement, and operational efficiency. Financial Administration & Business Operations • Build and manage retreat budgets, forecasts, and financial trackers. • Manage invoicing, deposits, payment schedules, supplier payments, and reconciliations. • Monitor profitability, margins, and overall retreat financial performance. • Support contract reviews, business reporting, and operational metrics. • Contribute to the development of retreat offerings, pricing models, operational processes, and scalable business infrastructure. • Continuously improve the client experience, operational efficiency, and overall growth of Moniker Executive Retreats. The Ideal Candidate: • Has 5+ years of experience in operations, hospitality, retreat planning, event planning, travel, concierge/executive services, business operations, or a related field. • Experience managing projects from sale through delivery. • Strong financial and budget management skills. • Experience working with CRM platforms, databases, websites, and operational software. • Exceptional organizational and project management abilities. • Comfortable managing multiple projects and competing priorities simultaneously. • Excellent written, verbal, and phone communication skills. • Confident building relationships with clients, property partners, suppliers, and industry contacts. • Ability to work independently in a fast-paced, entrepreneurial environment. You'll Be Great In This Role If: • You thrive in fast-moving environments and enjoy helping build systems, processes, and best practices as a business grows. • You are highly organized, detail-oriented, and take pride in keeping information accurate, up-to-date, and well managed. • You enjoy building relationships and are comfortable picking up the phone to connect with clients, suppliers, and partners. • You are proactive, resourceful, and don't wait to be told what to do. • You enjoy researching, sourcing, and uncovering new opportunities, whether that's a retreat property, supplier, destination, or business partnership. • You naturally look for ways to improve efficiency, create structure, and solve problems. • You take ownership of your work, follow through on commitments, and are comfortable being accountable for outcomes. • You enjoy being part of a collaborative team and are always willing to jump in where needed. This Role Won't Be a Good Fit If: • You prefer highly structured environments where every process, system, and decision has already been built for you. • You dislike managing multiple projects, priorities, and deadlines at the same time. • You prefer focusing on a single area of expertise rather than wearing multiple hats across sales, operations, partnerships, systems, and planning. • You're uncomfortable picking up the phone, building relationships, or having conversation