Executive Assistant / Chief of Staff

Job Summary
DentistFind, a premier Canadian marketing technology company with 14 years of experience supporting dental practices globally, is seeking a highly skilled Executive Assistant / Chief of Staff to support the CEO. This pivotal role balances managing routine operational tasks with driving strategic initiatives, enabling the CEO to concentrate on vision, sales, and company growth. The ideal candidate will expertly leverage AI tools, demonstrate strong problem-solving abilities, and independently oversee key processes. This fully remote position involves collaborating with a diverse, international team to enhance communication, streamline workflows, and ensure alignment across departments.

Key Responsibilities
- Decision Triage & First-Pass Resolution: Efficiently review incoming requests from email, Slack, and project management boards, independently resolving 70–80% of routine issues while escalating only unique or critical matters to the CEO.
- AI-Driven Research & Reporting: Utilize AI platforms such as ChatGPT to draft briefs, summarize complex data, and produce clear “What/Why/Outcome/Input” documents that support informed decision-making.
- Calendar & Project Management: Proactively manage the CEO’s calendar by blocking focus time, coordinating cross-department projects, and maintaining regular status updates with action-item tracking to ensure deadlines are met.
- Process & SOP Management: Identify operational bottlenecks and inefficiencies, propose improvements, document new standard operating procedures (SOPs), and lead system-wide training initiatives to enhance productivity.
- High-Level Communications: Prepare, draft, and proofread executive communications, including board meeting materials, investor updates, and client-facing reports, ensuring accuracy and professionalism.
- Stakeholder Liaison: Collaborate closely with Marketing, Sales, Client Success, Finance, and HR teams to maintain alignment and ensure timely delivery of key initiatives.
- Risk & “Luck” Monitoring: Maintain weekly dashboards tracking runway and risk factors, providing early warnings of potential issues to support proactive management.

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 comparable role supporting C-suite executives.
- Advanced proficiency with AI tools, including ChatGPT and prompt engineering techniques.
- Exceptional written and verbal communication skills, with a proven track record of preparing executive-level documents.
- Demonstrated ability to independently triage and resolve complex operational tasks.
- 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 sectors.
- Knowledge of Google Ads, Meta Ads, and CRM platforms.
- Proven success in documenting SOPs and developing training materials.
- Experience working within remote, multicultural teams.
- Demonstrated integrity and discretion in handling confidential information.

DentistFind offers a dynamic, fast-paced work environment that encourages innovation and professional growth with international exposure. This full-time, remote role offers flexible shifts between 6 AM and 5 PM EST, Monday through Friday. The global team spans the Philippines, Nigeria, Pakistan, Indonesia, and India, fostering a collaborative culture grounded in analytical decision-making, speed, strategic focus, continuous improvement, integrity, transparency, and viewing challenges as opportunities.

This position reports directly to the CEO and requires a strong alignment with company values and a commitment to confidentiality. Interested candidates should apply via the company’s official job board for prompt consideration.