Executive Assistant / Chief of Staff

Job Summary
DentistFind, a premier Canadian marketing technology company with 14 years of experience supporting dental practices worldwide, is seeking a highly skilled Executive Assistant / Chief of Staff to support the CEO. This critical role involves managing the CEO’s daily tasks and spearheading strategic initiatives, requiring strong AI literacy, excellent problem-solving abilities, and independent decision-making. The successful candidate will oversee key operational workflows, draft executive-level communications, and foster collaboration across departments, allowing the CEO to concentrate on vision, sales, and growth. DentistFind offers a stable, prestigious, and remote-first work environment, with opportunities for professional development and international exposure within a diverse, global team.

Key Responsibilities
- Decision Triage & First-Pass Resolution: Manage inbound requests from email, Slack, and project management platforms, independently resolving 70–80% of routine issues and escalating only novel or critical matters to the CEO.
- AI-Driven Research & Reporting: Leverage AI tools such as ChatGPT to draft briefs, summarize complex data, and produce concise “What/Why/Outcome/Input” documents that support informed decision-making.
- Calendar & Project Management: Oversee the CEO’s calendar by blocking focused work periods, coordinating cross-department initiatives, and providing regular status updates and action tracking to ensure alignment and progress.
- Process & SOP Management: Identify operational bottlenecks, recommend improvements, and document new standard operating procedures (SOPs). Train staff on updated processes to enhance organizational efficiency.
- High-Level Communications: Prepare and proofread CEO communications, board meeting materials, investor updates, and client-facing reports with precision and professionalism.
- Stakeholder Liaison: Collaborate closely with Marketing, Sales, Client Success, Finance, and HR teams to maintain alignment and ensure timely delivery of key objectives.
- Risk & “Luck” Monitoring: Maintain weekly dashboards tracking financial runway and risk factors, providing early warnings to the CEO about potential critical issues.

Required Qualifications
- Bachelor’s degree in Business, Communications, or a related discipline.
- At least 5 years of experience as an Executive Assistant, Chief of Staff, or in a similar role supporting C-suite executives.
- Expert proficiency with AI tools including ChatGPT and prompt engineering techniques.
- Exceptional written and verbal communication skills, with proven experience drafting executive-level materials.
- Demonstrated ability to independently triage and resolve complex tasks efficiently.
- Strong organizational skills and familiarity with project management tools such as Freedcamp, Asana, or Notion.
- Project management certifications are highly desirable.

Preferred Qualifications and Benefits
- Master of Business Administration (MBA) or equivalent advanced degree.
- Experience in marketing or professional services industries.
- Knowledge of Google Ads, Meta Ads, and CRM platforms.
- Proven success in documenting SOPs and developing training materials.
- Experience working within remote, multicultural teams.
- Ability to handle confidential information with utmost integrity and discretion.

DentistFind cultivates a culture focused on analytical decision-making, agility, strategic clarity, continuous improvement, integrity, and transparency. The company embraces challenges as opportunities for innovation and offers a fast-paced, dynamic environment where employees can make a significant impact on the growth of dental practices globally. Professional development and career growth are actively supported within a collaborative, remote work culture.

This is a full-time, remote position with a Monday to Friday schedule, offering two shift options between 6:00 AM and 5:00 PM EST. The Executive Assistant will join a vibrant, globally distributed team spanning the Philippines, Nigeria, Pakistan, Indonesia, and India, working closely with the CEO and department heads to drive strategic alignment and organizational success.