Community Support Services jobs in Ontario

EXECUTIVE & PERSONAL ASSISTANT

• Mississauga, ON | Monday–Friday | Hybrid (On-Site + Virtual)
• The successful candidate must be available to work onsite up to 3-days per week.
• Hours of Work: 9am to 4pm

About Us

The Pink Lion Business Coaching Corporation (TPL), is a business coaching, leadership development and people strategy company, designed for 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. 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.

Our Benefits

• Flexible work environment where you will have the opportunity to work 2-5 days per week from home, and the other days you will work at the CEO’s personal home
• Casual dress
• Flex hours and half day Fridays before every long weekend
• Unpaid week off between Christmas and New Year’s
• Summer Hours
• Health & Wellness Spending Account
• RRSP
• Work-life Balance
• Career growth, development, and continuous learning opportunities
• Fun and outgoing professional environment that really cares and values its employees

The Opportunity

The Executive & Personal Assistant is a trusted strategic partner to the CEO, helping bring structure, momentum, and calm to a fast-growing business dedicated to supporting 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.

Key Job Responsibilities

Executive Administration:

• Run the CEO’s day like a control tower
• 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
• Apply tools like ChatGPT, Claude, and others to draft communications, summarize information, create checklists, and streamline workflows
• Manage all personal, financial, and business matters with absolute discretion
• 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 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 are AI-curious and automation-minded
• You have high judgment; you know when to ask vs. when to act
• You are organized, precise, and discreet. You notice small details that prevent big problems
• You bring a hospitality-minded approach, and a strong work ethic
• You have an entrepreneurial curiosity, are highly collaborative and not afraid to challenge the status quo
• You enjoy speaking with people, and have high integrity when dealing with sensitive situations
• You love dogs (my hypoallergenic Maltipoo puppy expects affection) lol!
• 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 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.

We are committed to Diversity, Neurodiversity, Equity and Belonging. 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 opportunity for growth, ownership, and evolution as the company expands. This position has the potential to grow into a Manager role.

What You Have

• 5+ years experience working as an executive or administrative 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

If you are excited about this opportunity, we are so excited to hear from you!

Pay: $70,000.00-$90,000.00 per year

Ability to commute/relocate:

• Mississauga, ON L5L 5P7: reliably commute or plan to relocate before starting work (required)

Education:

• Bachelor's Degree (preferred)

Experience:

• Administrative: 5 years (required)

Work Location: Hybrid remote in Mississauga, ON L5L 5P7