Executive Assistant to CEO / Founder (Remote)

Actionable.co; Toronto; Remote; CAD 50,000 - 80,000; Full time

Job summary

Actionable.co is seeking an Executive Assistant to join their Toronto team. This role requires excellent organizational skills to support the CEO, manage communications, and assist with project coordination. Ideal candidates are proactive and tech-savvy, with strong communication abilities. Experience in financial oversight and client management is essential.

Qualifications

• Experience managing financial tasks such as invoicing and payments.
• Located in Canada, preferably in Central, Eastern, or Atlantic time zones.
• Experience in a remote-first environment.

Responsibilities

• Manage the CEO's inbox and prioritize emails.
• Oversee calendar management and scheduling.
• Assist in drafting and sending client updates.

Skills

Organization

Communication

Problem-Solving

Client Management

Time Management

Tools

Google Workspace

Hubspot

Slack

Job description

Actionable is a tech-enabled coaching company that helps impact focused leadership consultants deepen client relationships by proving the impact of their programs. We consider ourselves a software AND a service business where we provide world-class onboarding and coaching services to our clients in addition to our proprietary behavior change software. The Habit Builder system that helps workshop participants apply what they learned, organizations measure the return on their investment and consultants differentiate from the sea of training providers.

About the Role

Chris posted a short video about the role on LinkedIn.

We are looking for a smart, proactive, and highly organized individual to join our team as the Executive Assistant to the CEO / Founder . In this role, you act as a key "second brain" for the business, working hand-in-glove with the Founder to advance and realize the vision for the business. You will be responsible for administrative tasks, assisting with marketing-related activities, client communication, and project coordination across all business operations. Strong written and spoken English skills are essential, as you will be the primary point of communication for internal teams and external stakeholders.

It is crucial that you possess excellent interpersonal skills and can make everyone you interact with feel seen, heard, and respected. If you have a passion for organization, marketing-related support, and client engagement, we encourage you to apply for this exciting opportunity.

Key Responsibilities

World-Class Administrative Professional :

• Manage the CEO's inbox, prioritize emails, and handle action items.
• Oversee calendar management, scheduling, and meeting coordination.
• Take detailed notes during meetings, track action items, and ensure follow-ups.
• Handle internal and external communications on behalf of the CEO.

Marketing-Related Assistance :

• Maintain and update marketing assets.
• Catalog, review and analyze campaign results.

Client Communication and Relationship Management :

• Interact with clients in a professional and timely manner.
• Assist in coordinating client communications and follow-ups.
• Assist in drafting and sending client updates, reports, and communications.

Documentation and Process Optimization :

• Create and maintain Standard Operating Procedures (SOPs).
• Ensure all processes are well-documented and continuously improved.
• Utilize tools like Hubspot & Google Drive to organize information.

Operational and Project Support :

• Provide project management assistance to the CEO.
• Collaborate with multiple departments to ensure smooth execution of projects.
• Prioritize tasks effectively to help the CEO stay focused on strategic initiatives.

Ideal Candidate

• Highly Organized : You thrive in an organized environment but also lean into the chaos that comes with working for a bootstrapped business
• Strong Communicator : You have excellent written and verbal communication skills and are comfortable speaking on behalf of leadership.
• Financially Savvy : You have experience with basic financial management and can oversee payments, invoicing, and cash flow tracking.
• Proactive Problem-Solver : You anticipate needs before they arise and take action without being asked.
• Tech-Savvy : You're familiar with tools like Google Workspace, Slack, and Hubspot, and can quickly adapt to new technologies.
• Client-Focused : You understand the importance of client relationships and can manage communications professionally and efficiently.

Experience and Qualifications

Required :

• Applicants must be located in Canada (Central, Eastern, or Atlantic time zone preferred).
• Experience in a remote-first environment.
• Excellent written and verbal communication skills.
• Strong administrative and organizational skills.
• Experience managing financial tasks such as invoicing, payments, and cash flow.
• Ability to handle sensitive information with confidentiality and discretion.

Preferred :

• Experience working with executives and supporting high-level business operations.
• Passion for working with data and using insights to drive efficiency.
• Experience in the SaaS industry or supporting SaaS-based businesses.
• Strong interest in helping companies scale and improve operational effectiveness.
• Experience working with AI-driven tools or a curiosity about integrating AI into business processes.

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