Executive Assistant Operations (Toronto)

Schedule: Monday - Friday: 9am to 4pm Hybrid: Work from home up to 3 days per week Salary Range: $65,000 - $75,000 About Us The Pink Lion Business Coaching Corporation (TPL), is a business coaching, leadership development and people strategy company, designed for female business owners who are ready to expand their businesses, deepen their confidence, and intentionally build lives they love. As a Certified Executive and Business ActionCOACH Global Franchise Partner, the CEO uses the proven ActionCOACH framework to guarantee our clients achieve success. Under our services umbrella, we are creating The Pink Lion PowerHER Collective membership. This is a community for women business owners. It’s a place where collaboration replaces competition, where knowledge is shared freely, and where friendships are formed that go far beyond traditional business collaborations. This Collective is intentionally inclusive. Women who identify as neuro-diverse or, as Sarah affectionately calls it, “neuro-spicy” are welcomed and supported. Not only is Sarah a certified Business & Executive Coach, but she is also a certified ADHD Coach; truly understanding what it means to think differently, feel deeply, and thrive outside traditional business norms. The Opportunity The Operations Executive Assistant is a trusted strategic partner to the CEO, helping bring structure, momentum, and calm to a fast-growing business dedicated to supporting female entrepreneurs. This role is ideal for someone who loves creating order from complexity, building systems that help people thrive, and being deeply involved in meaningful work that positively impacts others. You will play a central role in helping scale both the business and the growing PowerHER community, while supporting a founder who values authenticity, innovation, collaboration, and human connection. The ideal candidate is highly resourceful, proactive, emotionally intelligent, and energized by variety. One moment you may be coordinating an event, another streamlining workflows with AI tools, supporting client experiences, managing operations, or helping create more ease and efficiency behind the scenes. This role is best suited for someone who enjoys being a true right-hand partner in a purpose-driven entrepreneurial environment. Key Job Responsibilities Executive Administration: - Run the CEO’s day like a control tower. - Build in daily/weekly schedules and reminders before each block of meetings/events, including “prep now”, “start travel”, “planning time”. - Time management for in-person meetings. Track traffic and transit times so that reminders reflect when to leave, not just when a meeting starts. Adjust alerts if conditions change. - Build simple automations so this process gets smarter over time. - Keep communication and follow-through tight. - Track decisions, follow-ups, and priories in a shared note with CEO. Nudge the right people at the right time to keep things moving. - Coordinate communications and liaise directly with external partners, vendors, and clients - Act as a trusted gatekeeper, screening calls, emails, and sensitive requests - Plan and organize events, meetings, and client-related functions - Use AI and automation to increase leverage. - Apply tools like ChatGPT, Claude, and others to draft communications, summarize information, create checklists, and streamline scheduling workflows. - Set up and maintain simple automations (rules, zaps, shortcuts, scripts, etc.) that reduce repetitive work and help the CEO stay on track. - Manage all personal, financial, and business matters with absolute discretion - Maintain confidential files, records, and transactions securely - Desire and ability to learn the ActionCOACH business system and best practices to support the CEO and client process Business Operations: - Your work behind the scenes will directly contribute to helping female business owners grow their confidence, leadership, businesses, and communities. - Support client-facing initiatives and ensure the smooth execution of programs, events and operations. - Contribute to the planning, organization, and execution of special projects - including high-profile events and key organizational initiatives - Presenting at events and preforming basic sales initiatives of current programs and products - Manage the company's social media presence, drafting social media posts, reaching out to new potential business connections and answering direct messages Personal Assistant: - Light home management support tasks, such as running errands, coordinating returns, completing shopping and general home organization - Organize, track and reconcile personal and professional finances and expenses, thereby ensuring the CEO spends as little time as possible worrying about administrative tasks, and as much time as possible growing the business - Provide occasional pet care when needed You are Perfect for This Role Because - Calendar and time management is your superpower. You have experience managing a high-volume, frequently changing calendars for a senior leader, founder, or equivalent. - AI-curious and automation-minded. You already use AI tools in your work or personal life. You enjoy experimenting with new tech, setting up automations, and continuously improving your systems. - High judgment: you know when to ask vs. when to act. You’re comfortable asking clear, concise questions when context is missing. You know when to pause and clarify versus when to take a best-effort step and move things forward. You’re proactive without being reckless. - Organized, precise, and discreet. You notice small details that prevent big problems. You handle sensitive information with confidentiality and professionalism. You communicate clearly and succinctly in writing and verbally. - You are comfortable with direct, honest communication and able to adapt quickly in a fast-moving entrepreneurial workplace. - This role occasionally requires flexibility outside traditional business hours during high-priority situations, events, or schedule changes. We value proactive communication, reliability, and strong judgment in navigating fast-moving situations while also supporting sustainable ways of working. - You have compassion, and maybe experience, supporting individuals with ADHD or executive-function differences - You are passionate, enthusiastic and motivated by success, assisting the business in operating in a seamless fashion, identifying needs and completing tasks as they arise to assure that the CEO and business can operate in an effective manner. - You are a highly professional and work exceptionally well independently. You bring a hospitality-minded approach, and a strong work ethic. You are resourceful, detail-oriented, and calm under pressure. - You communicate professionally, are not shy to offer gentle reminders to the CEO when helpful, and build trust through reliability, discretion, and follow-through. - You have an entrepreneurial curiosity, are highly collaborative and not afraid to challenge the status quo. - You are agile and able to deal with ambiguity while translating complex business issues into clear and coherent solutions that drive impact. - You take pride in your work and take the initiative to work outside normal business hours if required to complete your projects on time - You are a terrific coach to others, a positive role model, enjoy speaking with people, and have high integrity when dealing with sensitive situations - You are creative, solution-focused, and love sharing ideas - You love dogs (my hypoallergenic Maltipoo puppy expects affection) - You enjoy having fun at work; life is too short to be serious all the time. Why People Love Working Here This is not a traditional corporate executive assistant role. At The Pink Lion, you’ll have the opportunity to contribute to a growing business that is deeply focused on empowering women entrepreneurs to build businesses and lives they genuinely love. You’ll work closely with a founder who values creativity, authenticity, innovation, collaboration, and meaningful relationships. Your ideas, initiative, and contributions will matter here. We believe in building a business culture where people can be themselves, continue learning, challenge the status quo, and do work that feels purposeful. Our team shows up as their authentic selves. We are committed to Diversity, Neurodiversity, Equity and Belonging. We believe that different perspectives, skills, backgrounds, and experiences, result in higher-performing teams and better innovation. We are happy to help during any part of the recruitment process and invite you to let us know how we can help make the overall process easier for you. Career Growth This role offers significant opportunity for growth, ownership, and evolution as the company expands. This position has the potential to grow into an Operations Manager role. What You Have - 5+ years experience working as an executive assistant or a proven track record of success providing administrative coordination in a professional setting - Post-secondary education in Business Administration or a related field is preferred - A positive mindset and a \"can-do\" attitude, with a passion to learn and grow - Working camera or webcam on your personal desktop/laptop - Access to a reliable high speed internet connection - Strong computer skills to prepare data analysis, reports, and presentations - Valid driver's license and reliable transportation (mileage reimbursement provided for work-related tasks; candidate uses their own vehicle) - This role may involve occasional travel (a valid passport is a required) - Must be flexible with working hours and available as needed in urgent situations Please note: We do not offer employment sponsorships. This role is open to Canadian citizens, permanent residents, and valid Canadian work-permit holders only. Compensation This role requires comfort with responsibility, …