Executive Assistant: AI-First & Proactive Support for Startup EdTech CEO

We’re seeking a highly experienced, proactive, and tech-savvy Executive Assistant to support the CEO of an innovative EdTech startup on a fractional basis. This role is ideal for someone who thrives in fast-paced environments, excels in automation and efficiency, and has a track record of supporting startup executives. If you’re an AI-first thinker who loves using technology to streamline operations and drive impact, we want to hear from you.

???? Role at a Glance:

Hours: 5-10 hours per week to start, with potential for growth
Location: Fully remote
Start Date: ASAP

???? Key Responsibilities
Strategic Time & Inbox Management: Own the CEO’s email and calendar, ensuring seamless scheduling, time optimization, and prioritization of key initiatives.
High-Level Administrative Support: Handle traditional EA tasks such as travel arrangements, expense tracking, meeting preparation, and follow-ups.
Automation & AI Implementation: Leverage AI and automation tools (including ChatGPT, Zapier, and Notion) to streamline workflows and improve efficiency.
Business Development Support: Conduct cold email outreach and LinkedIn engagement to build relationships and generate leads.
Content & Marketing Assistance: Create and manage visually compelling content using Canva for newsletters, social media, and presentations.

Email Marketing & CRM Management: Assist with email campaigns in Klaviyo, list segmentation, and performance tracking.

???? Required Skills & Experience
Prior Experience Supporting Startup CEOs: At least 3+ years as an EA, Chief of Staff, or similar role in a fast-paced startup environment.
Exceptional Communication & Attention to Detail: Strong written and verbal communication skills, with the ability to craft clear, concise, and professional correspondence.
AI & Automation Proficiency: Experience using AI tools (e.g., ChatGPT, Claude) and workflow automation platforms (Zapier, Airtable, Notion). Bonus if you’ve built custom GPTs or have experience with prompt engineering.
Marketing & Outreach Expertise: Experience with LinkedIn outreach, email marketing (Klaviyo), and CRM management.
Design & Content Creation Skills: Familiarity with Canva or other design tools to create visually engaging content.
Self-Starter & Problem-Solver: Ability to anticipate needs, take initiative, and work independently in a fully remote setting.

? Why Join Us?
Mission-Driven Work: We’re transforming postsecondary education by connecting students with high-ROI career pathways. Your work will directly support this mission.
Opportunity for Growth: Start with 5-10 hours per week, with potential for increased responsibilities and hours as we scale.
Work with Cutting-Edge Tech: Be at the forefront of AI and automation, using the latest tools to enhance efficiency and impact.
If you’re an experienced, resourceful, and tech-forward Executive Assistant who thrives on making things run smoothly and efficiently, we’d love to hear from you!