Senior Executive Assistant to CEO | Remote, Fast-Paced

Dapple; Connecticut; Hybrid; USD 100,000 - 170,000; Full time

Benefits offered by this job

Medical, dental, vision, disability

401(k)

Maternity/Parental leave

6 weeks PTO

Flexible work schedules

Job summary

Dapple is seeking an experienced Executive Assistant to the CEO to keep the CEO’s world running and free her to focus on high-leverage work. You will own the calendar, inbox and travel, act as a discreet gatekeeper, and coordinate meetings, materials and follow-ups across a fast-moving organization.

Beyond daily support, you’ll help sustain rhythm and culture, organizing offsites, team events and company swag for a distributed, remote-first team across time zones.

Qualifications

• 5+ years as an executive assistant to a CEO, founder or senior executive, ideally in startup or fast-moving environment.
• Exceptional gatekeeper with mastery of complex calendars and independent time management.
• Exceptional organization, discretion and reliability with confidential, high-stakes information.
• Proactive, low ego; anticipates needs and owns details.

Responsibilities

• Own the CEO's calendar, inbox and travel with the judgment to prioritize, decline and reschedule.
• Be an exceptional gatekeeper: protect time and surface what needs attention.
• Prepare the CEO for meetings with agendas, materials, briefing notes and follow-ups.
• Handle scheduling, expenses, documents and day-to-day tasks to prevent slips.
• Plan and coordinate company programs and team events, including offsite and swag.
• Maintain the small but important things that hold the company together.

Skills

Executive support to CEO

Calendar management

Gatekeeper

Discretion

Reliability

Written communication

Microsoft 365

DocuSign

Tools

Microsoft 365

DocuSign

Job description

Dapple is seeking an experienced Executive Assistant to the CEO to keep the CEO’s world running and free her to focus on high-leverage work. You will own the calendar, inbox and travel, act as a discreet gatekeeper, and coordinate meetings, materials and follow-ups across a fast-moving organization.

Beyond daily support, you’ll help sustain rhythm and culture, organizing offsites, team events and company swag for a distributed, remote-first team across time zones.